Download PDF
Synthesis 2022; 54(16): 3499-3557
DOI: 10.1055/a-1783-0751
review

Advances in the Synthesis of Enterobactin, Artificial Analogues, and Enterobactin-Derived Antimicrobial Drug Conjugates and Imaging Tools for Infection Diagnosis

Philipp Klahn  ∗
a   Institute of Organic Chemistry, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany
b   Department for Chemistry and Molecular Biology, University of Gothenburg, Kemigården 4, 41296 Göteborg, Sweden
,
Robert Zscherp
a   Institute of Organic Chemistry, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany
,
Claire C. Jimidar
a   Institute of Organic Chemistry, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany
› Author AffiliationsThis work has been carried out within the framework of the SMART BIOTECS alliance between the Technische Universität Braunschweig and the Leibniz Universität Hannover. This initiative is supported by the Niedersächsisches Ministerium für Wissenschaft und Kultur (Ministry of Science and Culture (MWK) of Lower Saxony, Germany). Financially support by the Deutsche Forschungsgemeinschaft (Grant KL3012/2-1) and Fonds der Chemischen Industrie is gratefully acknowledged. The content of this work is solely the responsibility of the authors and does not necessarily represent the official views of the funding agencies.
› Further Information
    Permissions and Reprints All articles of this category


In memoriam of Prof. Dr. Dieter Enders

Abstract

Iron is an essential growth factor for bacteria, but although highly abundant in nature, its bioavailability during infection in the human host or the environment is limited. Therefore, bacteria produce and secrete siderophores to ensure their supply of iron. The triscatecholate siderophore enterobactin and its glycosylated derivatives, the salmochelins, play a crucial role for iron acquisition in several bacteria. As these compounds can serve as carrier molecules for the design of antimicrobial siderophore drug conjugates as well as siderophore-derived tool compounds for the detection of infections with bacteria, their synthesis and the design of artificial analogues is of interest. In this review, we give an overview on the synthesis of enterobactin, biomimetic as well as totally artificial analogues, and related drug-conjugates covering up to 12/2021.

1 Introduction

2 Antibiotic Crisis and Sideromycins as Natural Templates for New Antimicrobial Drugs

3 Biosynthesis of Enterobactin, Salmochelins, and Microcins

4 Total Synthesis of Enterobactin and Salmochelins

5 Chemoenzymatic Semi-synthesis of Salmochelins and Microcin E492m Derivatives

6 Synthesis of Biomimetic Enterobactin Derivatives with Natural Tris-lactone Backbone

7 Synthesis of Artificial Enterobactin Derivatives without Tris-lactone Backbone

8 Conclusions

Key words

enterobactin - salmochelins - microcins - siderophores - drug conjugates - catecholates - tris-lactone - iron(III) chelator


Publication History

Received: 15 January 2022

Accepted after revision: 28 February 2022

Accepted Manuscript online:
28 February 2022

Article published online:
17 May 2022

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

  • 1 Sánchez M, Sabio L, Gálvez N, Capdevila M, Dominguez-Vera JM. IUBMB Life 2017; 69: 382
    CrossrefPubMed
  • 2 Andreini C, Putignano V, Rosato A, Banci L. Metallomics 2018; 10: 1223
    CrossrefPubMed
  • 3 Durham B, Millett FS. Iron: Heme Proteins & Electron Transport. In Encyclopedia of Inorganic and Bioinorganic Chemistry [Online]. Wiley & Sons, Posted December 15, 2011; 15.12.2011
    Google Scholar
  • 4 Sousa JS, D’Imprima E, Vonck J. In Membrane Protein Complexes: Structure and Function . Harris JR, Boekema EJ. Springer Singapore; Singapore: 2018: 167
    CrossrefGoogle Scholar
  • 5 Harel A, Bromberg Y, Falkowski PG, Bhattacharya D. Proc. Natl. Acad. Sci. U. S. A. 2014; 111: 7042
    CrossrefPubMed
  • 6 Poulos TL. Chem. Rev. 2014; 114: 3919
    CrossrefPubMed
  • 7 Yamanaka T, Okunuti K. In Microbial Iron Metabolism: A Comprehensive Treatise . Neilands JB. Academic Press; New York: 1974: 349-400
    CrossrefGoogle Scholar
  • 8 Yancey RJ, Breeding SA. L, Lankford CE. Infect. Immun. 1979; 24: 174
    CrossrefPubMed
  • 9 Burris RH, Orme-Johnson WH. In Microbial Iron Metabolism: A Comprehensive Treatise . Neilands JB. Academic Press; New York: 1974: 187-209
    CrossrefGoogle Scholar
  • 10 Atkin CL, Thelander L, Reichard P. J. Biol. Chem. 1973; 248: 7464
    CrossrefPubMed
  • 11 Payne SM, Neilands IB. Crit. Rev. Microbiol. 1988; 16: 81
    CrossrefPubMed
  • 12 Davis KA, Hatefi Y. Biochemistry 1971; 10: 2509
    CrossrefPubMed
  • 13 Schröder I, Johnson E, De Vries S. FEMS Microbiol. Rev. 2003; 27: 427
    CrossrefPubMed
  • 14 Gkouvatsos K, Papanikolaou G, Pantopoulos K. Biochim. Biophys. Acta, Gen. Subj. 2012; 1820: 188
    CrossrefPubMed
  • 15 Rosa L, Cutone A, Lepanto MS, Paesano R, Valenti P. Int. J. Mol. Sci. 2017; 18: 1985
    CrossrefPubMed
  • 16 Harrison PM, Arosio P. Biochim. Biophys. Acta 1996; 1275: 161
    CrossrefPubMed
  • 17 Zhang J, Chen X, Hong J, Tang A, Liu Y, Xie N, Nie G, Yan X, Liang M. Sci. China Life Sci. 2021; 64: 352
    CrossrefPubMed
  • 18 Fenton HJ. H. J. Chem. Soc. Trans. 1894; 65: 899
    Crossref
  • 19 Klahn P, Brönstrup M. Nat. Prod. Rep. 2017; 34: 832
    CrossrefPubMed
  • 20 Ganz T, Nemeth E. Am. J. Physiol.: Gastrointest. Liver Physiol. 2006; 290: 199
  • 21 Gammella E, Buratti P, Cairo G, Recalcati S. Metallomics 2014; 6: 1336
    CrossrefPubMed
  • 22 Ganz T. Int. J. Hematol. 2018; 107: 7
    CrossrefPubMed
  • 23 Sukhbaatar N, Weichhart T. Pharmaceuticals 2018; 11: 137
    CrossrefPubMed
  • 24 Golonka R, Yeoh BS, Vijay-Kumar M. J. Innate Immun. 2019; 11: 249
    CrossrefPubMed
  • 25 Cassat JE, Skaar EP. Cell Host Microbe 2013; 13: 509
    CrossrefPubMed
  • 26 Hider RC, Kong X. Nat. Prod. Rep. 2010; 27: 637
    CrossrefPubMed
  • 27 Saha R, Saha N, Donofrio RS, Bestervelt LL. J. Basic Microbiol. 2013; 53: 303
    CrossrefPubMed
  • 28 Neilands JB. J. Biol. Chem. 1995; 270: 26723
    CrossrefPubMed
  • 29 Klebba PE, Newton SM. C, Six DA, Kumar A, Yang T, Nairn BL, Munger C, Chakravorty S. Chem. Rev. 2021; 121: 5193
    CrossrefPubMed
  • 30 Raymond KN, Dertz EA, Kim SS. Proc. Natl. Acad. Sci. U. S. A. 2003; 100: 3584
    CrossrefPubMed
  • 31 Bister B, Bischoff D, Nicholson GJ, Valdebenito M, Schneider K, Winkelmann G, Hantke K, Süssmuth RD. BioMetals 2004; 17: 471
    CrossrefPubMed
  • 32 Klebba PE. Front. Biosci. 2003; 8: 1422
    CrossrefPubMed
  • 33 Watts RE, Totsika M, Challinor VL, Mabbett AN, Ulett GC, Voss JJ. D, Schembri MA. Infect. Immun. 2012; 80: 333
    CrossrefPubMed
  • 34 Jalal MA. F, van der Helm D. FEBS Lett. 1989; 243: 366
    CrossrefPubMed
  • 35 Rabsch W, Voigt W, Reissbrodt R, Tsolis RM, Bäumler AJ. J. Bacteriol. 1999; 181: 3610
    CrossrefPubMed
  • 36 Buchanan SK, Smith BS, Venkatramani L, Xia D, Esser L, Palnitkar M, Chakraborty R, van der Helm D, Deisenhofer J. Nat. Struct. Biol. 1999; 6: 56
    CrossrefPubMed
  • 37 Russo TA, McFadden CD, Carlino-MacDonald UB, Beanan JM, Barnard TJ, Johnson JR. Infect. Immun. 2002; 70: 7156
    CrossrefPubMed
  • 38 Braun V, Braun M. FEBS Lett. 2002; 529: 78
    CrossrefPubMed
  • 39 Raymond KN, Allred BE, Sia AK. Acc. Chem. Res. 2015; 48: 2496
    CrossrefPubMed
  • 40 Johnstone TC, Nolan EM. Dalton Trans. 2015; 44: 6320
    CrossrefPubMed
  • 41 Holden VI, Bachman MA. Metallomics 2015; 7: 986
    CrossrefPubMed
  • 42 Schmiederer T, Rausch S, Valdebenito M, Mantri Y, Mösker E, Baramov T, Stelmaszyk K, Schmieder P, Butz D, Müller SI, Schneider K, Baik M.-H, Hantke K, Süssmuth RD. Angew. Chem. Int. Ed. 2011; 50: 4230
    CrossrefPubMed
  • 43 Baramov T, Keijzer K, Irran E, Mösker E, Baik MH, Süssmuth R. Chem. Eur. J. 2013; 19: 10536
    CrossrefPubMed
  • 44 Saha P, Yeoh BS, Olvera RA, Xiao X, Singh V, Awasthi D, Subramanian BC, Chen Q, Dikshit M, Wang Y, Parent CA, Vijay-Kumar M. J. Immunol. 2017; 198: 4293
    CrossrefPubMed
  • 45 Behnsen J, Rafatellu M. Mbio 2016; 7: e01906
    CrossrefPubMed
  • 46 Wilson BR, Bogdan AR, Miyazawa M, Hashimoto K, Tsuji Y. Trends Mol. Med. 2016; 1471
  • 47 Saha P, Yeoh BS, Xiao X, Golonka RM, Kumarasamy S, Vijay-Kumar M. Biochem. Pharmacol. 2019; 168: 71
    CrossrefPubMed
  • 48 Saha P, Yeoh BS, Xiao X, Golonka RM, Abokor AA, Wenceslau CF, Shah YM, Joe B, Vijay-Kumar M. Gut Microbes 2020; 12: 1841548
    CrossrefPubMed
  • 49 Qi B, Han M. Cell 2018; 175: 571
    CrossrefPubMed
  • 50 Costas M, Mehn MP, Jensen MP, Que L. Chem. Rev. 2004; 104: 939
    CrossrefPubMed
  • 51 Scarrow RC, Ecker DJ, Ng C, Liu S, Raymond KN. Inorg. Chem. 1991; 30: 900
    Crossref
  • 52 Loomis LD, Raymond KN. Inorg. Chem. 1991; 30: 906
    Crossref
  • 53 Müller SI, Valdebenito M, Hantke K. BioMetals 2009; 22: 691
    CrossrefPubMed
  • 54 Fischbach MA, Lin H, Liu DR, Walsh CT. Nat. Chem. Biol. 2006; 2: 132
    CrossrefPubMed
  • 55 Guo C, Steinberg LK, Cheng M, Song JH, Henderson JP, Gross ML. ACS Chem. Biol. 2020; 15: 1154
    CrossrefPubMed
  • 56 Zhu W, Winter MG, Spiga L, Beiting DP, Hooper LV, Winter SE, Zhu W, Winter MG, Spiga L, Hughes ER, Chanin R, Mulgaonkar A, Hooper LV, Winter SE. Cell Host Microbe 2020; 27: 1
    CrossrefPubMed
  • 57 Singh V, Yeoh BS, Xiao X, Kumar M, Bachman M, Borregaard N, Joe B, Vijay-Kumar M. Nat. Commun. 2015; 6: 7113
    CrossrefPubMed
  • 58 Vander ElstN, Breyne K, Steenbrugge J, Gibson AJ, Smith DG. E, Germon P, Werling D, Meyer E. Front. Vet. Sci. 2020; 7: 576583
    CrossrefPubMed
  • 59 Wang H, Zeng X, Lin J. Vaccine 2020; 38: 7764
    CrossrefPubMed
  • 60 Abergel RJ, Clifton MC, Pizarro JC, Warner JA, Shuh DK, Strong RK, Raymond KN. J. Am. Chem. Soc. 2008; 130: 11524
    CrossrefPubMed
  • 61 Wang H, Zeng X, Mo Y, He B, Lin H, Lin J. Appl. Environ. Microbiol. 2019; 85: e00358
    PubMed
  • 62 Zeng X, Wang H, Huang C, Logue CM, Barbieri NL, Nolan LK, Lin J. Front. Immunol. 2021; 12: 629480
    CrossrefPubMed
  • 63 Hantke K, Nicholson G, Rabsch W, Winkelmann G. Proc. Natl. Acad. Sci. U. S. A. 2003; 100: 3677
    CrossrefPubMed
  • 64 Nagy TA, Moreland SM, Andrews-Polymenis H, Detweiler CS. Infect. Immun. 2013; 81: 4063
    CrossrefPubMed
  • 65 Crouch ML. V, Castor M, Karlinsey JE, Kalhorn T, Fang FC. Mol. Microbiol. 2008; 67: 971
    CrossrefPubMed
  • 66 Lam MM. C, Wyres KL, Judd LM, Wick RR, Jenney A, Brisse S, Holt KE. Genome Med. 2018; 10: 77
    CrossrefPubMed
  • 67 Caza M, Garénaux A, Lépine F, Dozois CM. Mol. Microbiol. 2015; 97: 717
    CrossrefPubMed
  • 68 Chairatana P, Zheng T, Nolan EM. Chem. Sci. 2015; 6: 4458
    CrossrefPubMed
  • 69 Fiedler H, Krastel P, Müller J, Gebhardt K, Zeeck A. FEMS Microbiol. Lett. 2001; 196: 147
    CrossrefPubMed
  • 70 Mislin GL, Schalk IJ. Metallomics 2014; 6: 408
    CrossrefPubMed
  • 71 Heymann P, Ernst JF, Winkelmann G. BioMetals 2000; 13: 65
    CrossrefPubMed
  • 72 Lesuisse E, Simon-Casteras M, Labbe P. Microbiology 1998; 144: 3455
    CrossrefPubMed
  • 73 Haas H, Schoeser M, Lesuisse E, Ernst JF, Parson W, Abt B, Winkelmann G, Oberegger H. Biochem. J. 2003; 371: 505
    CrossrefPubMed
  • 74 Haas H. Nat. Prod. Rep. 2014; 31: 1266
    CrossrefPubMed
  • 75 Karpishin TB, Dewey TM, Raymond KN. J. Am. Chem. Soc. 1993; 115: 1842
    Crossref
  • 76 Hou Z, Stack TD. P, Sunderland CJ, Raymond KN. Inorg. Chim. Acta 1997; 263: 341
    Crossref
  • 77 Karpishin TB, Raymond KN. Angew. Chem. Int. Ed. 1992; 31: 466
    Crossref
  • 78 Abergel RJ, Warner JA, Shuh DK, Raymond KN. J. Am. Chem. Soc. 2006; 128: 8920
    CrossrefPubMed
  • 79 Dean CR, Poole K. J. Bacteriol. 1993; 175: 317
    CrossrefPubMed
  • 80 Moynié L, Milenkovic S, Mislin GL. A, Gasser V, Malloci G, Baco E, Mccaughan RP, Page MG. P, Schalk IJ, Ceccarelli M, Naismith JH. Nat. Commun. 2019; 10: 3673
    CrossrefPubMed
  • 81 Dean CR, Neshat S, Poole K. J. Bacteriol. 1996; 178: 5361
    CrossrefPubMed
  • 82 Moynié L, Luscher A, Rolo D, Pletzer D, Tortajada A, Weingart H, Braun Y, Page MG. P, Naismith JH, Köhler T. Antimicrob. Agents Chemother. 2017; 61: e02531
    CrossrefPubMed
  • 83 Noinaj N, Rollauer SE, Buchanan SK. Curr. Opin. Struct. Biol. 2015; 31: 35
    CrossrefPubMed
  • 84 Vergalli J, Bodrenko IV, Masi M, Moynié L, Acosta-Gutiérrez S, Naismith JH, Davin-Regli A, Ceccarelli M, van den Berg B, Winterhalter M, Pagès J.-M. Nat. Rev. Microbiol. 2020; 18: 164
    CrossrefPubMed
  • 85 Johnstone TC, Nolan EM. J. Am. Chem. Soc. 2017; 139: 15245
    CrossrefPubMed
  • 86 Peuckert F, Miethke M, Albrecht AG, Essen LO, Marahiel MA. Angew. Chem. Int. Ed. 2009; 48: 7924
    CrossrefPubMed
  • 87 Peuckert F, Ramos-Vega AL, Miethke M, Schwörer CJ, Albrecht AG, Oberthür M, Marahiel MA. Chem. Biol. 2011; 18: 907
    CrossrefPubMed
  • 88 Liu X, Du Q, Wang Z, Liu S, Li N, Chen Y, Zhu C, Zhu D, Wei T, Huang Y, Xu S, Gu L. FEBS Lett. 2012; 586: 1240
    CrossrefPubMed
  • 89 Flores Jiménez RH, Cafiso DS. Biochemistry 2012; 51: 3642
    CrossrefPubMed
  • 90 Klebba PE. J. Bacteriol. 2016; 198: 1013
    CrossrefPubMed
  • 91 Jordan LD, Zhou Y, Smallwood CR, Lill Y, Ritchie K, Yip WT, Newton SM, Klebba PE. Proc. Natl. Acad. Sci. U. S. A. 2013; 110: 11553
    CrossrefPubMed
  • 92 Majumdar A, Trinh V, Moore KJ, Smallwood CR, Kumar A, Yang T, Scott DC, Long NJ, Newton SM, Klebba PE. J. Biol. Chem. 2020; 295: 4974
    CrossrefPubMed
  • 93 Higgs PI, Larsen RA, Postle K. Mol. Microbiol. 2002; 44: 271
    CrossrefPubMed
  • 94 Chimento DP, Kadner RJ, Wiener MC. Proteins Struct. Funct. Genet. 2005; 59: 240
    CrossrefPubMed
  • 95 Shultis DD, Purdy MD, Banchs CN, Wiener MC. Science 2006; 312: 1396
    CrossrefPubMed
  • 96 Moeck GS, Coulton JW. Mol. Microbiol. 1998; 28: 675
    CrossrefPubMed
  • 97 Köster W. Res. Microbiol. 2001; 152: 291
    CrossrefPubMed
  • 98 Braun V. Int. J. Med. Microbiol. 2001; 291: 67
    CrossrefPubMed
  • 99 Larsen NA, Lin H, Wei R, Fischbach MA, Walsh CT. Biochemistry 2006; 45: 10184
    CrossrefPubMed
  • 100 Perraud Q, Cantero P, Roche B, Gasser V. Mol. Cell. Proteomics 2020; 19: 589
    CrossrefPubMed
  • 101 Pelfrene E, Botgros R, Cavaleri M. Antimicrob. Resist. Infect. Control 2021; 10: 21
    CrossrefPubMed
  • 102 Lucien MA. B, Canarie MF, Kilgore PE, Jean-Denis G, Fénélon N, Pierre M, Cerpa M, Joseph GA, Maki G, Zervos MJ, Dely P, Boncy J, Sati H, del Rio A, Ramon-Pardo P. Int. J. Infect. Dis. 2021; 104: 250
    CrossrefPubMed
  • 103 Sriram A, Kapoor G, Craig J, Balasubramanian R, Brar S, Criscuolo N, Hamilton A, Klein E, Tseng K, Van Boeckel TP, Laxminarayan R. The State of the World’s Antibiotics 2021 . The Center for Disease Dynamics, Economics & Policy (CDDEP); Washington DC: 2021
    Google Scholar
  • 104 O’Neill, J. Tackling Drug-Resistant Infections Globally 2016.
  • 105 Davies J. Can. J. Infect. Dis. Med. Microbiol. 2006; 17: 287
    CrossrefPubMed
  • 106 Moloney MG. Trends Pharmacol. Sci. 2016; 37: 689
    CrossrefPubMed
  • 107 Klahn P, Brönstrup M. Curr. Top. Microbiol. Immunol. 2016; 389: 365
  • 108 Boucher HW, Talbot GH, Bradley JS, Edwards JE, Gilbert D, Rice LB, Scheld M, Spellberg B, Bartlett J. Clin. Infect. Dis. 2009; 48: 1
    CrossrefPubMed
  • 109 Boucher HW, Talbot GH, Benjamin DK, Bradley J, Guidos RJ, Jones RN, Murray BE, Bonomo RA, Gilbert D. Clin. Infect. Dis. 2013; 56: 1685
    CrossrefPubMed
  • 110 Peterson LR. Clin. Infect. Dis. 2009; 49: 992
    CrossrefPubMed
  • 111 Global Priority List of Antibiotic-Resistant Bacteria to Guide Research, Discovery, and Development of New Antibiotics (WHO/EMP/IAU/2017.12). World Health Organization; Geneva: 2017
    Google Scholar
  • 112 Prioritization of Pathogens to Guide Discovery, Research and Development of New Antibiotics for Drug-Resistant Bacterial Infections, Including Tuberculosis (WHO/EMP/IAU/2017.12). World Health Organization; Geneva: 2017
    Google Scholar
  • 113 Cooper MA, Shlaes D. Nature 2011; 472: 32
    CrossrefPubMed
  • 114 Piddock LJ. V. Lancet Infect. Dis. 2012; 12: 249
    CrossrefPubMed
  • 115 Ventola CL. J. Formul. Manag. 2015; 40: 277
  • 116 Wright GD. ACS Infect. Dis. 2015; 1: 80
    CrossrefPubMed
  • 117 Li X.-Z, Plésiat P, Nikaido H. Clin. Microbiol. Rev. 2015; 28: 337
    CrossrefPubMed
  • 118 Farhat N, Ali A, Bonomo RA, Khan AU. Drug Discov. Today 2020; 25: 2307
    CrossrefPubMed
  • 119 Zhou G, Shi Q, Huang X, Xie X. Int. J. Mol. Sci. 2015; 16: 21711
    CrossrefPubMed
  • 120 Vassiliadis G, Destoumieux-Garzón D, Lombard C, Rebuffat S, Peduzzi J. Antimicrob. Agents Chemother. 2010; 54: 288
    CrossrefPubMed
  • 121 Braun V, Pramanik A, Gwinner T, Köberle M, Bohn E. BioMetals 2009; 22: 3
    CrossrefPubMed
  • 122 Duquesne S, Destoumieux-Garzón D, Peduzzi J, Rebuffat S. Nat. Prod. Rep. 2007; 24: 708
    CrossrefPubMed
  • 123 Budzikiewicz H. Curr. Top. Med. Chem. 2001; 1: 73
    CrossrefPubMed
  • 124 Górska A, Sloderbach A, Marszałł MP. Trends Pharmacol. Sci. 2014; 35: 442
    CrossrefPubMed
  • 125 Ji C, Juárez-Hernández RE, Miller MJ. Future Med. Chem. 2012; 4: 297
    CrossrefPubMed
  • 126 Skwarecki AS, Milewski S, Schielmann M, Milewska MJ. Nanomed. Nanotechnol., Biol. Med. 2016; 12: 2215
    CrossrefPubMed
  • 127 Page MG. P. Ann. N. Y. Acad. Sci. 2013; 1277: 115
    CrossrefPubMed
  • 128 Bickel H, Gaeumann E, Keller-Schierlein W, Prelog V, Vischer E, Wettstein A, Zaehner H. Experentia 1960; 16: 129
    CrossrefPubMed
  • 129 Benz G, Schröder T, Kurz J, Wünsche C, Karl W, Steffens G, Pfitzner J, Schmidt D. Angew. Chem. Int. Ed. 1982; 21: 527
    Crossref
  • 130 Zeng Y, Kulkarni A, Yang Z, Patil PB, Zhou W, Chi X, Van Lanen S, Chen S. ACS Chem. Biol. 2012; 7: 1565
    CrossrefPubMed
  • 131 Stefanska AL, Fulston M, Houge-Frydrych CS, Jones JJ, Warr SR. J. Antibiot. 2000; 53: 1346
    CrossrefPubMed
  • 132 Pramanik A, Braun V. J. Bacteriol. 2006; 188: 3878
    CrossrefPubMed
  • 133 Braun V, Gunthner K, Hantke K, Zimmermann L. J. Bacteriol. 1983; 156: 308
    CrossrefPubMed
  • 134 Vertesy L, Aretz W, Fehlhaber H.-W, Kogler H. Helv. Chim. Acta 1995; 78: 46
    Crossref
  • 135 Bickel H, Mertens P, Prelog V, Seibl J, Walser A. Antimicrob. Agents Chemother. 1965; 5: 951
    PubMed
  • 136 Tsukiura H, Okanishi M, Omori T, Koshiyama H, Miyaki T, Kitajima H, Kawaguchi H. J. Antibiot. 1964; 17: 3947
  • 137 Huber P, Leuenberger H, Keller-Schierlein W. Helv. Chim. Acta 1986; 69: 236
    Crossref
  • 138 Palmer JD, Mortzfeld BM, Piattelli E, Silby MW, McCormick BA, Bucci V. ACS Infect. Dis. 2020; 6: 672
    CrossrefPubMed
  • 139 Thomas X, Destoumieux-Garzón D, Peduzzi J, Afonso C, Blond A, Birlirakis N, Goulard C, Dubost L, Thai R, Tabet JC, Rebuffat S. J. Biol. Chem. 2004; 279: 28233
    CrossrefPubMed
  • 140 Strahsburger E, Baeza M, Monasterio O, Lagos R. Antimicrob. Agents Chemother. 2005; 49: 3083
    CrossrefPubMed
  • 141 De Lorenzo V, Pugsley AP. Antimicrob. Agents Chemother. 1985; 27: 666
    CrossrefPubMed
  • 142 Bieler S, Silva F, Soto C, Belin D. J. Bacteriol. 2006; 188: 7049
    CrossrefPubMed
  • 143 Destoumieux-Garzón D, Thomas X, Santamaria M, Goulard C, Barthélémy M, Boscher B, Bessin Y, Molle G, Pons AM, Letellier L, Peduzzi J, Rebuffat S. Mol. Microbiol. 2003; 49: 1031
    CrossrefPubMed
  • 144 Sargun A, Gerner RR, Raffatellu M, Nolan EM. J. Infect. Dis. 2021; 223: S307
    CrossrefPubMed
  • 145 Wencewicz TA, Miller MJ. Top. Med. Chem. 2017; 26: 151
    Crossref
  • 146 Schalk I. J. Clin. Microbiol. Infect. 2018; 24: 801
    CrossrefPubMed
  • 147 Negash KH, Norris JK. S, Hodgkinson JT. Molecules 2019; 24
    PubMed
  • 148 Kong H, Cheng W, Wei H, Yuan Y, Yang Z, Zhang X. Eur. J. Med. Chem. 2019; 182: 111615
    CrossrefPubMed
  • 149 Möllmann U, Heinisch L, Bauernfeind A, Köhler T, Ankel-Fuchs D. BioMetals 2009; 22: 615
    CrossrefPubMed
  • 150 Li K, Chen WH, Bruner SD. BioMetals 2016; 29: 377
    CrossrefPubMed
  • 151 Petrik M, Zhai C, Haas H, Decristoforo C. Clin. Transl. Imaging 2017; 5: 15
    CrossrefPubMed
  • 152 Zscherp R, Coetzee J, Vornweg J, Grunenberg J, Herrmann J, Müller R, Klahn P. Chem. Sci. 2021; 12: 10179
    CrossrefPubMed
  • 153 Ferreira K, Hu HY, Fetz V, Prochnow H, Rais B, Müller PP, Brönstrup M. Angew. Chem. Int. Ed. 2017; 56: 8272
    CrossrefPubMed
  • 154 Nosrati R, Dehghani S, Karimi B, Yousefi M, Taghdisi SM, Abnous K, Alibolandi M, Ramezani M. Biosens. Bioelectron. 2018; 117: 1
    CrossrefPubMed
  • 155 Southwell JW, Black CM, Duhme-Klair AK. ChemMedChem 2021; 16: 1063
    CrossrefPubMed
  • 156 Zheng T, Nolan EM. Metallomics 2012; 4: 866
    CrossrefPubMed
  • 157 Sattely ES, Fischbach MA, Walsh CT. Nat. Prod. Rep. 2008; 25: 757
    CrossrefPubMed
  • 158 Reitz ZL, Sandy M, Butler A. Metallomics 2017; 9: 824
    CrossrefPubMed
  • 159 Gehring AM, Bradley KA, Walsh CT. Biochemistry 1997; 36: 8495
    CrossrefPubMed
  • 160 May JJ, Wendrich TM, Marahiel MA. J. Biol. Chem. 2001; 276: 7209
    CrossrefPubMed
  • 161 Bluhm ME, Kim SS, Dertz EA, Raymond KN. J. Am. Chem. Soc. 2002; 124: 2436
    CrossrefPubMed
  • 162 Budzikiewicz H, Bössenkamp A, Taraz K, Pandey A, Meyer J.-M. Z. Naturforsch. C 1997; 52: 551
    Crossref
  • 163 Wen Y, Wu X, Teng Y, Qian C, Zhan Z, Zhao Y, Li O. Environ. Microbiol. 2011; 13: 2726
    CrossrefPubMed
  • 164 Patzer SI, Braun V. J. Bacteriol. 2010; 192: 426
    CrossrefPubMed
  • 165 Matsuo Y, Kanoh K, Jang JH, Adachi K, Matsuda S, Miki O, Kato T, Shizuri Y. J. Nat. Prod. 2011; 74: 2371
    CrossrefPubMed
  • 166 Zane HK, Naka H, Rosconi F, Sandy M, Haygood MG, Butler A. J. Am. Chem. Soc. 2014; 136: 5615
    CrossrefPubMed
  • 167 Sandy M, Han A, Blunt J, Munro M, Haygood M, Butler A. J. Nat. Prod. 2010; 73: 1038
    CrossrefPubMed
  • 168 Han AW, Sandy M, Fishman B, Trindade-Silva AE, Soares CA. G, Distel DL, Butler A, Haygood MG. PLoS One 2013; 8 (10) : e76151
    CrossrefPubMed
  • 169 Süssmuth RD, Mainz A. Angew. Chem. Int. Ed. 2017; 56: 3770
    CrossrefPubMed
  • 170 Valdebenito M, Bister B, Reissbrodt R, Hantke K, Winkelmann G. Int. J. Med. Microbiol. 2005; 295: 99
    CrossrefPubMed
  • 171 Yu X, Dai Y, Yang T, Gagné MR, Gong H. Tetrahedron 2011; 67: 144
    Crossref
  • 172 Foshag D, Campbell C, Pawelek PD. Biochim. Biophys. Acta, Proteins Proteomics 2014; 1844: 1619
    CrossrefPubMed
  • 173 Fischbach MA, Lin H, Liu DR, Walsh CT. Proc. Natl. Acad. Sci. U. S. A. 2005; 102: 571
    CrossrefPubMed
  • 174 Caza M, Lépine F, Milot S, Dozois CM. Infect. Immun. 2008; 76: 3539
    CrossrefPubMed
  • 175 Nolan EM, Fischbach MA, Koglin A, Walsh CT. J. Am. Chem. Soc. 2007; 129: 14336
    CrossrefPubMed
  • 176 Nolan EM, Walsh CT. Biochemistry 2008; 47: 9289
    CrossrefPubMed
  • 177 Corey EJ, Bhattacharyya S. Tetrahedron Lett. 1977; 18: 3919
    Crossref
  • 178 Rastetter WH, Erickson TJ, Venuti MC. J. Org. Chem. 1981; 46: 3579
    Crossref
  • 179 Rogers HJ. J. Chem. Soc., Perkin Trans. 1 1995; 3073
    Crossref
  • 180 Shanzer A, Libman J. J. Chem. Soc., Chem. Commun. 1983; 846
    Crossref
  • 181 Ramirez RJ. A, Karamanukyan L, Ortiz S, Gutierrez CG. Tetrahedron Lett. 1997; 38: 749
    Crossref
  • 182 Marinez ER, Salmassian EK, Lau TT, Gutierrez CG. J. Org. Chem. 1996; 61: 3548
    Crossref
  • 183 Rastetter WH, Erickson TJ, Venuti MC. J. Org. Chem. 1980; 45: 5011
    Crossref
  • 184 Masamune S, Hayase Y, Chan WS. W. K, Bates GS. J. Am. Chem. Soc. 1977; 99: 6756
    CrossrefPubMed
  • 185 Neilands JB, Erickson TJ, Rastetter WH. J. Biol. Chem. 1981; 256: 3831
    CrossrefPubMed
  • 186 Shanzer A, Libman J, Frolow F. J. Am. Chem. Soc. 1981; 103: 7339
    Crossref
  • 187 Shanzer A, Libman J. J. Organomet. Chem. 1982; 239: 301
    Crossref
  • 188 Sheehan JC, Hasspacher K, Yeh YL. J. Am. Chem. Soc. 1959; 81: 6086
    Crossref
  • 189 Considine WJ. J. Organomet. Chem. 1966; 5: 263
    Crossref
  • 190 Meyer M, Telford JR, Cohen SM, White DJ, Xu J, Raymond KN, March RV. J. Am. Chem. Soc. 1997; 119: 10093
    Crossref
  • 191 Gong H, Gagné MR. J. Am. Chem. Soc. 2008; 130: 12177
    CrossrefPubMed
  • 192 Lee AA, Chen YC. S, Ekalestari E, Ho SY, Hsu NS, Kuo TF, Wang TA. S. A. Angew. Chem. Int. Ed. 2016; 55: 12338
    CrossrefPubMed
  • 193 Gantt RW, Peltier-Pain P, Cournoyer WJ, Thorson JS. Nat. Chem. Biol. 2011; 7: 685
    CrossrefPubMed
  • 194 Isied SS, Kuo G, Raymond KN. J. Am. Chem. Soc. 1976; 98: 1763
    CrossrefPubMed
  • 195 Sargun A, Sassone-Corsi M, Zheng T, Raffatellu M, Nolan EM. ACS Infect. Dis. 2021; 7: 1248
    CrossrefPubMed
  • 196 Nodwell MB, Britton R. ACS Infect. Dis. 2020; 7: 153
    CrossrefPubMed
  • 197 du Moulinet d’Hardemare A, Alnaga N, Serratrice G, Pierre JL. Bioorg. Med. Chem. Lett. 2008; 18: 6476
    CrossrefPubMed
  • 198 Baramov T, Schmid B, Ryu H, Jeong J, Keijzer K, von Eckardstein L, Baik MH, Süssmuth RD. Chem. Eur. J. 2019; 25: 6955
    CrossrefPubMed
  • 199 Weizman H, Shanzer A. Chem. Commun. 2000; 2013
    Crossref
  • 200 Du Moulinet D’Hardemare A, Gellon G, Philouze C, Serratrice G. Inorg. Chem. 2012; 51: 12142
    CrossrefPubMed
  • 201 Zheng T, Bullock JL, Nolan EM. J. Am. Chem. Soc. 2012; 134: 18388
    CrossrefPubMed
  • 202 Zheng T, Nolan EM. J. Am. Chem. Soc. 2014; 136: 9677
    CrossrefPubMed
  • 203 Neumann W, Sassone-Corsi M, Raffatellu M, Nolan EM. J. Am. Chem. Soc. 2018; 140: 5193
    CrossrefPubMed
  • 204 Sargun A, Johnstone TC, Zhi H, Raffatellu M, Nolan E. Chem. Sci. 2021; 12: 4041
    CrossrefPubMed
  • 205 Abergel RJ, Moore EG, Strong RK, Raymond KN. J. Am. Chem. Soc. 2006; 128: 10998
    CrossrefPubMed
  • 206 Cohen SM, Raymond KN. Inorg. Chem. 2000; 39: 3624
    CrossrefPubMed
    • 207a E. coli ATCC 33475 (ΔentA) lacks genes, necessary for the biosynthesis of Ent, but retains the capacity to import and metabolize Ent.
    • 207b Wayne R, Frick K, Neilands JB. J. Bacteriol. 1976; 126: 7
      CrossrefPubMed
    • 207c E. coli H1187 (ΔfepA) lacks the outer membrane receptor for Ent and therefore cannot import the siderophore.
    • 207d E. coli K-12 JW0576 (Δfes) can accumulate ferric Ent, but cannot release the iron because it is deficient in the Ent esterase Fes.
    • 207e P. aeruginosa K648 (Δpvd/pch) is deficient in the biosynthesis of both pyoverdine (Pvd) and pyochelin(Pch) siderophores.
    • 207f P. aeruginosa K407 (Δpvd/pFr) is deficient in the biosynthesis of Pvd and lacks the enterobactin specific siderophore receptor PfeA.
    • 207g Poole K, Young L, Neshat S. J. Bacteriol. 1990; 172: 6991
      CrossrefPubMed
    • 207h E. coli K-12 (+iroD) is a mutant of the non-pathogenic laboratory strain E. coli K-12 which was complemented with the iroD gene.
    • 207i E. coli CFT073 (ΔiroD) lacks the gene necessary for the expression of iroD.
    • 207j E. coli K-12 (ΔentA) comparable to E. coli ATCC 33475 (ΔentA), lacks genes, necessary for the biosynthesis of enterobactin, but retains the capacity to import and metabolize enterobactin.
  • 208 Abergel RJ, Zawadzka AM, Hoette TM, Raymond KN. J. Am. Chem. Soc. 2009; 131: 12682
    CrossrefPubMed
  • 209 Mulvey MA, Schilling JD, Hultgren SJ. Infect. Immun. 2001; 69: 4572
    CrossrefPubMed
  • 210 Mobley HL, Green DM, Trifillis AL, Johnson DE, Chippendale GR, Lockatell CV, Jones BD, Warren JW. Infect. Immun. 1990; 58: 1281
    CrossrefPubMed
  • 211 Henderson JP, Crowley JR, Pinkner JS, Walker JN, Tsukayama P, Stamm WE, Hooton TM, Hultgren SJ. PLoS Pathog. 2009; 5: e1000305
    CrossrefPubMed
  • 212 Bourgat Y, Mikolai C, Stiesch M, Klahn P, Menzel H. Antibiotics 2021; 10: 653
    CrossrefPubMed
  • 213 Cramariuc O, Rog T, Javanainen M, Monticelli L, Polishchuk AV, Vattulainen I. Biochim. Biophys. Acta, Biomembr. 2012; 1818: 2563
    CrossrefPubMed
  • 214 Cormier R, Burda WN, Harrington L, Edlinger J, Kodigepalli KM, Thomas J, Kapolka R, Roma G, Anderson BE, Turos E, Shaw LN. Bioorg. Med. Chem. Lett. 2012; 22: 6513
    CrossrefPubMed
  • 215 Kaper JB, Nataro JP, Mobley HL. T. Nat. Rev. Microbiol. 2004; 2: 123
    CrossrefPubMed
  • 216 Valdebenito M, Müller SI, Hantke K. FEMS Microbiol. Lett. 2007; 277: 182
    CrossrefPubMed
  • 217 Goetz DH, Holmes MA, Borregaard N, Bluhm ME, Raymond KN, Strong RK. Mol. Cell 2002; 10: 1033
    CrossrefPubMed
  • 218 Centers for Disease Control and Prevention (CDC). Surveillance for Foodborne Disease Outbreaks, United States, 2017, Annual Report. U.S. Department of Health and Human Services, CDC; Atlanta GA: 2019
    Google Scholar
  • 219 Neumann W, Nolan EM. J. Biol. Inorg. Chem. 2018; 23: 1025
    CrossrefPubMed
  • 220 Shanzer A, Libman J, Lifson S, Felder CE. J. Am. Chem. Soc. 1986; 108: 7609
    CrossrefPubMed
  • 221 Glindemann CP, Backenköhler A, Strieker M, Wittstock U, Klahn P. ChemBioChem 2019; 20: 2341
    CrossrefPubMed
  • 222 Dale JA, Dull DL, Mosher HS. J. Org. Chem. 1969; 34: 2543
    Crossref
  • 223 Nicolaou KC, Estrada AA, Zak M, Lee SH, Safina BS. Angew. Chem. Int. Ed. 2005; 44: 1378
    CrossrefPubMed
  • 224 Gerlach H, Thalmann A. Helv. Chim. Acta 1974; 57: 2661
    Crossref
  • 225 Corey EJ, Nicolaou KC. J. Am. Chem. Soc. 1974; 96: 5614
    CrossrefPubMed
  • 226 Ji C, Miller PA, Miller MJ. J. Am. Chem. Soc. 2012; 134: 9898
    CrossrefPubMed
  • 227 Ohi N, Aoki B, Kuroki T, Matsumoto M, Kojima K, Nehashi T. J. Antibiot. 1987; 40: 22
    CrossrefPubMed
  • 228 Nicolaou KC, Yin J, Mandal D, Erande RD, Klahn P, Jin M, Aujay M, Sandoval J, Gavrilyuk J, Vourloumis D. J. Am. Chem. Soc. 2016; 138: 1698
    CrossrefPubMed
  • 229 Klahn P, Fetz V, Ritter A, Collisi W, Hinkelmann B, Arnold T, Tegge W, Rox K, Hüttel S, Mohr KI, Wink J, Stadler M, Wissing J, Jänsch L, Brönstrup M. Chem. Sci. 2019; 10: 5187
    CrossrefPubMed
  • 230 Neilands JB, Konopka K. Biochemistry 1984; 23: 2122
    CrossrefPubMed
  • 231 Aisen P, Listowsky I. Annu. Rev. Biochem. 1980; 49: 357
    CrossrefPubMed
  • 232 Pollack JR, Neilands JB. Biochem. Biophys. Res. Commun. 1970; 38: 989
    CrossrefPubMed
  • 233 Zhou T, Ma Y, Kong X, Hider RC. Dalton Trans. 2012; 41: 6371
    CrossrefPubMed
  • 234 Hider RC, Singh S, Porter JB. Proc. R. Soc. Edinburgh, Sect. B: Biol. Sci. 1992; 99 (01) 137-168
    Crossref
  • 235 du Moulinet d’Hardemare A, Serratrice G, Pierre J.-L. Mini-Rev. Org. Chem. 2010; 7: 125
    CrossrefPubMed
  • 236 Baco E, Hoegy F, Schalk IJ, Mislin GL. A. Org. Biomol. Chem. 2014; 12: 749
    CrossrefPubMed
  • 237 Perraud Q, Cantero P, Munier M, Hoegy F, Zill N, Gasser V, Mislin GL. A, Ehret-Sabatier L, Schalk IJ. Microorganisms 2020; 8: 1
    CrossrefPubMed
  • 238 D’Amato A, Ghosh P, Costabile C, Della Sala G, Izzo I, Maayan G, De Riccardis F. Dalton Trans. 2020; 49: 6020
    CrossrefPubMed
  • 239 Oh J, Kang D, Hong S, Kim SH, Choi JH, Seo J. Dalton Trans. 2021; 50: 3459
    CrossrefPubMed
  • 240 Rodgers SJ, Lee C, Ng CY, Raymond KN. Inorg. Chem. 1987; 26: 1622
    CrossrefPubMed
  • 241 Anderson MT, Armstrong SK. J. Bacteriol. 2006; 188: 5731
    CrossrefPubMed
  • 242 Heinisch L, Gebhardt P, Heidersbach R, Reissbrodt R, Möllmann U. BioMetals 2002; 15: 133
    CrossrefPubMed
  • 243 McMurry TJ, Rodgers SJ, Raymond KN. J. Am. Chem. Soc. 1987; 109: 3451
    Crossref
  • 244 Thomas F, Beguin C, Pierre JL, Serratrice G. Inorg. Chim. Acta 1999; 291: 148
    Crossref
  • 245 Baret P, Béguin C, Gaude D, Gellon G, Mourral C, Pierre JL, Serratrice G, Favier A. Tetrahedron 1994; 50: 2077
    Crossref
  • 246 Baret P, Beaujolais V, Béguin C, Gaude D, Pierre JL, Serratrice G. Eur. J. Inorg. Chem. 1998; 613
    Crossref
  • 247 Pierre J, Serratrice G, Baret P, Be C, Saint-aman E, Thomas F, Laulhe J. Eur. J. Inorg. Chem. 2000; 1219
  • 248 Serratrice G, Biaso F, Thomas F, Béguin C. Eur. J. Inorg. Chem. 2004; 1552
    Crossref
  • 249 Baret P, Beguin CG, Boukhalfa H, Caris C, Laulhere J.-P, Pierre J.-L, Serratrice G. J. Am. Chem. Soc. 1995; 117: 9760
    Crossref
  • 250 Serratrice G, Boukhalfa H, Béguin C, Baret P, Caris C, Pierre JL. Inorg. Chem. 1997; 36: 3898
    CrossrefPubMed
  • 251 Caris C, Baret P, Beguin C, Serratrice G, Pierre JL, Laulhère JP. Biochem. J. 1995; 312: 879
    CrossrefPubMed
  • 252 Henry C, Rakba N, Imbert D, Thomas F, Baret P, Serratrice G, Gaude D, Pierre JL, Ward RJ, Crichton RR, Lescoat G. Biochem. Pharmacol. 2001; 62: 1355
    CrossrefPubMed
  • 253 Caris C, Baret P, Pierre J.-L, Serratrice G. Tetrahedron 1996; 52: 4659
    Crossref
  • 254 Ng CY, Rodgers SJ, Raymond KN. Inorg. Chem. 1989; 28: 2062
    CrossrefPubMed
  • 255 Streater M, Taylor PD, Hider RC, Porter J. J. Med. Chem. 1990; 33: 1749
    CrossrefPubMed
  • 256 Xiao G, Der Van Helm D, Hider RC, Rai BL. J. Phys. Chem. 1996; 100: 2345
    CrossrefPubMed
  • 257 Gyparaki M, Porter JB, Hirani S, Streater M, Hider RC, Huehns ER. Acta Haematol. 1987; 78: 217
    CrossrefPubMed
  • 258 Piyamongkol S, Zhou T, Liu ZD, Khodr HH, Hider RC. Tetrahedron Lett. 2005; 46: 1333
    Crossref
  • 259 Xie Y.-Y, Liu M.-S, Hu P.-P, Kong X.-L, Qiu D.-H, Xu J.-L, Hider RC, Zhou T. Med. Chem. Res. 2013; 22: 2351
    CrossrefPubMed
  • 260 Xu J, Churchill DG, Botta M, Raymond KN. Inorg. Chem. 2004; 43: 5492
    CrossrefPubMed
  • 261 Xu J, Franklin SJ, Whisenhunt DW, Raymond KN. J. Am. Chem. Soc. 1995; 117: 7245
    CrossrefPubMed
  • 262 Doble DM. J, Botta M, Wang J, Aime S, Barge A, Raymond KN. J. Am. Chem. Soc. 2001; 123: 10758
    CrossrefPubMed
  • 263 Xu J, O’Sullivan B, Raymond KN. Inorg. Chem. 2002; 41: 6731
    CrossrefPubMed
  • 264 Puerta DT, Botta M, Jocher CJ, Werner EJ, Avedano S, Raymond KN, Cohen SM. J. Am. Chem. Soc. 2006; 128: 2222
    CrossrefPubMed
  • 265 Datta A, Raymond KN. Acc. Chem. Res. 2009; 42: 938
    CrossrefPubMed
  • 266 Stintzi A, Barnes C, Xu J, Raymond KN. Proc. Natl. Acad. Sci. U. S. A. 2000; 97: 10691
    CrossrefPubMed
  • 267 Turcot I, Stintzi A, Xu J, Raymond KN. J. Biol. Inorg. Chem. 2000; 5: 634
    CrossrefPubMed
  • 268 Dertz EA, Xu J, Raymond KN. Inorg. Chem. 2006; 45: 5465
    CrossrefPubMed
  • 269 Naikare H, Butcher J, Flint A, Xu J, Raymond KN, Stintzi A. Metallomics 2013; 5: 988
    CrossrefPubMed
  • 270 Cohen SM, O’Sullivan B, Raymond KN. Inorg. Chem. 2000; 39: 4339
    CrossrefPubMed
  • 271 Cohen SM, Xu J, Radkov E, Raymond KN, Botta M, Barge A, Aime S. Inorg. Chem. 2000; 39: 5747
    CrossrefPubMed
  • 272 Albrecht-Gary AM, Blanc S, Biaso F, Thomas F, Baret P, Gellon G, Pierre JL, Serratrice G. Eur. J. Inorg. Chem. 2003; 2596
    Crossref
  • 273 Hoette TM, Abergel RJ, Xu J, Strong RK, Raymond KN. J. Am. Chem. Soc. 2008; 130: 17584
    CrossrefPubMed
  • 274 Baral M, Gupta A, Akbar R, Kanungo BK. J. Appl. Chem. 2016; 2016: 3757418
    CrossrefPubMed
  • 275 Chaves S, Marques SM, Matos AM. F, Nunes A, Gano L, Tuccinardi T, Martinelli A, Santos MA. Chem. Eur. J. 2010; 16: 10535
    CrossrefPubMed
  • 276 Xu B, Kong X.-L, Zhou T, Qiu DH, Chen YL, Liu MS, Yang RH, Hider RC. Bioorg. Med. Chem. Lett. 2011; 21: 6376
    CrossrefPubMed
  • 277 Harris WR, Weitl FL, Raymond KN. J. Chem. Soc., Chem. Commun. 1979; 177
    Crossref
  • 278 Weitl FL, Harris WR, Raymond KN. J. Med. Chem. 1979; 22: 1281
    CrossrefPubMed
  • 279 Weitl FL, Raymond KN. J. Am. Chem. Soc. 1979; 101: 2728
    Crossref
  • 280 Carrano CJ, Raymond KN. J. Am. Chem. Soc. 1979; 101: 5401
    Crossref
  • 281 Pecoraro VL, Weitl FL, Raymond KN. J. Am. Chem. Soc. 1981; 103: 5133
    Crossref
  • 282 Kiggen W, Vögtle F. Angew. Chem. Int. Ed. 1984; 23: 714
    Crossref
  • 283 Rai BL, Khodr H, Hider RC. Tetrahedron 1999; 55: 1129
    CrossrefPubMed
  • 284 Xu J, Kullgren B, Durbin PW, Raymond KN. J. Med. Chem. 1995; 38: 2606
    CrossrefPubMed
  • 285 Stutte P, Kiggen W, Vögtle F. Tetrahedron 1987; 43: 2065
    Crossref
  • 286 McMurry TJ, Hosseini MW, Garrett TM, Hahn FE, Reyes ZE, Raymond KN. J. Am. Chem. Soc. 1987; 109: 7196
    CrossrefPubMed
  • 287 Venuti MC, Rastetter WH, Neilands JB. J. Med. Chem. 1979; 22: 123
    CrossrefPubMed
  • 288 Matzanke BF, Ecker DJ, Yang TS, Huynh BH, Müller G, Raymond KN. J. Bacteriol. 1986; 167: 674
    CrossrefPubMed
  • 289 Heidinger S, Braun V, Pecoraro VL, Raymond KN. J. Bacteriol. 1983; 153: 109
    CrossrefPubMed
  • 290 Ecker DJ, Loomis LD, Cass ME, Raymond KN. J. Am. Chem. Soc. 1988; 110: 2457
    CrossrefPubMed
  • 291 Pinkert L, Lai Y, Peukert C, Hotop S, Karge B, Schulze LM, Grunenberg J, Brönstrup M. J. Med. Chem. 2021; 64: 15440
    CrossrefPubMed
  • 292 Zhang Q, Jin B, Shi Z, Wang X, Liu Q, Lei S, Peng R. Sci. Rep. 2016; 6: 34024
    CrossrefPubMed
  • 293 Hayashi M, Ishii M, Hiratani K, Saigo K. Tetrahedron Lett. 1998; 39: 6215
    CrossrefPubMed
  • 294 Wang J, Oyler KD, Bernhard S. Inorg. Chem. 2007; 46: 5700
    CrossrefPubMed
  • 295 Ong SA, Peterson T, Neilands JB. J. Biol. Chem. 1979; 254: 1860
    CrossrefPubMed
  • 296 Eng-Wilmot DL, van der Helm D. J. Am. Chem. Soc. 1980; 102: 7719
    Crossref
  • 297 Griffiths GL, Sigel SP, Payne SM, Neilands JB. J. Biol. Chem. 1984; 259: 383
    CrossrefPubMed
  • 298 Kretchmar SA, Raymond KN. J. Am. Chem. Soc. 1986; 108: 6212
    Crossref
  • 299 Blainey J, Swanson S, Weitl FL, Raymond KN, Durbin PW. J. Med. Chem. 1981; 24: 5401
    Crossref
  • 300 Weitl FL, Raymond KN. J. Org. Chem. 1981; 46: 5234
    Crossref
  • 301 Kappel MJ, Pecoraro VL, Raymond KN. Inorg. Chem. 1985; 24: 2447
    CrossrefPubMed
  • 302 Sharma SK, Miller MJ, Payne SM. J. Med. Chem. 1989; 32: 357
    CrossrefPubMed
  • 303 Abergel RJ, Raymond KN. Inorg. Chem. 2006; 45: 3622
    CrossrefPubMed
  • 304 Ghosh A, Miller MJ. J. Org. Chem. 1993; 58: 7652
    CrossrefPubMed
  • 305 Ghosh M, Miller MJ. Bioorg. Med. Chem. 1996; 4: 43
    CrossrefPubMed
  • 306 Diarra MS, Lavoie MC, Jacques M, Darwish I, Dolence EK, Dolence JA, Ghosh A, Ghosh M, Miller MJ, Malouin F. Antimicrob. Agents Chemother. 1996; 40: 2610
    CrossrefPubMed
  • 307 Ghosh A, Ghosh M, Niu C, Malouin F, Moellmann U, Miller MJ. Chem. Biol. 1996; 3: 1011
    CrossrefPubMed
  • 308 Wencewicz TA, Miller MJ. J. Med. Chem. 2013; 56: 4044
    CrossrefPubMed
  • 309 Bohac TJ, Fang L, Banas VS, Giblin DE, Wencewicz TA. ACS Infect. Dis. 2021; 7: 2138
    CrossrefPubMed
  • 310 Proschak A, Lubuta P, Grün P, Löhr F, Wilharm G, De Berardinis V, Bode HB. ChemBioChem 2013; 14: 633
    CrossrefPubMed
  • 311 Ghosh M, Miller PA, Möllmann U, Claypool WD, Schroeder VA, Wolter WR, Suckow M, Yu H, Li S, Huang W, Zajicek J, Miller MJ. J. Med. Chem. 2017; 60: 4577
    CrossrefPubMed
  • 312 Ghosh M, Lin Y.-M, Miller PA, Möllmann U, Boggess W, Miller MJ. ACS Infect. Dis. 2018; 4: 1529
    CrossrefPubMed
  • 313 Ji C, Miller MJ. BioMetals 2015; 28: 541
    CrossrefPubMed
  • 314 Ghosh M, Miller PA, Miller MJ. J. Antibiot. 2020; 73: 152
    CrossrefPubMed
  • 315 Okoh OA, Klahn P. ChemBioChem 2018; 19: 1668
    CrossrefPubMed
  • 316 Jimidar CC, Grunenberg J, Karge B, Fuchs HL. S, Brönstrup M, Klahn P. Chem. Eur. J. 2021; 28: e202103525
    CrossrefPubMed
  • 317 Bollinger JE, Mague JT, Roundhill DM. Inorg. Chem. 1994; 33: 1241
    Crossref
  • 318 Bollinger JE, Mague JT, O’Connor CJ, Banks WA, Roundhill DM. J. Chem. Soc., Dalton Trans. 1995; 1677
    Crossref
  • 319 Sahoo SK, Bera RK, Kanungo BK, Baral M. Spectrochim. Acta, Part A 2012; 89: 322
    CrossrefPubMed
  • 320 Baral M, Sahoo SK, Kanungo BK. J. Inorg. Biochem. 2008; 102: 1581
    CrossrefPubMed
  • 321 Kanungo BK, Baral M, Sahoo SK, Muthu SE. Spectrochim. Acta, Part A 2009; 74: 544
    CrossrefPubMed
  • 322 Bera RK, Baral M, Sahoo SK, Kanungo BK. Spectrochim. Acta, Part A 2015; 134: 165
    CrossrefPubMed
  • 323 Grazina R, Gano L, Šebestík J, Santos MA. J. Inorg. Biochem. 2009; 103: 262
    CrossrefPubMed
  • 324 Akbar R, Baral M, Kanungo BK. Spectrochim. Acta, Part A 2021; 247: 119124
    CrossrefPubMed
  • 325 Tse B, Kishi Y. J. Org. Chem. 1994; 59: 7807
    CrossrefPubMed
  • 326 Zhu CF, Qiu DH, Kong X.-L, Hider RC, Zhou T. J. Pharm. Pharmacol. 2013; 65: 512
    CrossrefPubMed
  • 327 Zhou YJ, Liu MS, Osamah AR, Kong X.-L, Alsam S, Battah S, Xie YY, Hider RC, Zhou T. Eur. J. Med. Chem. 2015; 94: 8
    CrossrefPubMed
  • 328 Zhou T, Kong X.-L, Hider RC. Dalton Trans. 2019; 48: 3459
    CrossrefPubMed
  • 329 Imbert D, Thomas F, Baret P, Serratrice G, Gaude D, Pierre JL, Laulhère JP. New J. Chem. 2000; 24: 281
    CrossrefPubMed
  • 330 Imbert D, Baret P, Gaude D, Gautier-Luneau I, Gellon G, Thomas F, Serratrice G, Pierre JL. Chem. Eur. J. 2002; 8: 1091
    CrossrefPubMed
  • 331 Fardeau S, Dassonville-Klimpt A, Audic N, Sasaki A, Pillon M, Baudrin E, Mullié C, Sonnet P. Bioorg. Med. Chem. 2014; 22: 4049
    CrossrefPubMed
  • 332 Kita K, Kida T, Nakatsuji Y, Ikeda I. Chem. Lett. 1997; 26: 405
    Crossref
  • 333 Sun Y, Motekaitis RJ, Martell AE. Inorg. Chim. Acta 1998; 281: 60
    CrossrefPubMed
  • 334 Akbar R, Baral M, Kanungo BK. Spectrochim. Acta, Part A 2015; 142: 246
    CrossrefPubMed
  • 335 Akbar R, Baral M, Kanungo BK. RSC Adv. 2015; 5: 16207
    CrossrefPubMed
  • 336 Besserglick J, Olshvang E, Szebesczyk A, Englander J, Levinson D, Hadar Y, Gumienna-Kontecka E, Shanzer A. Chem. Eur. J. 2017; 23: 13181
    CrossrefPubMed
  • 337 Neff C, Bellot F, Waern JB, Lambert F, Brandel J, Serratrice G, Gaboriau F, Policar CJ. Inorg. Biochem. 2012; 112: 59
    CrossrefPubMed
  • 338 Ghosh M, Miller MJ. J. Org. Chem. 1994; 59: 1020
    CrossrefPubMed
  • 339 Ghosh M, Miller MJ. Bioorg. Med. Chem. 1995; 3: 1519
    CrossrefPubMed
  • 340 Bernier G, Girijavallabhan V, Murray A, Niyaz N, Ding P, Miller MJ, Malouin F. Antimicrob. Agents Chemother. 2005; 49: 241
    CrossrefPubMed
  • 341 Möllmann U, Ghosh A, Dolence EK, Dolence JA, Ghosh M, Miller MJ, Reissbrodt R. BioMetals 1998; 11: 1
    CrossrefPubMed
  • 342 Raymond KN, Müller G, Matzanke BF. Top. Curr. Chem. 1984; 123: 49
    Crossref
  • 343 Harris WR, Raymond KN, Weitl FL. J. Am. Chem. Soc. 1981; 103: 2667
    Crossref
  • 344 Esteves MA, Vaz MC. T, Gonçalves ML. S. S, Farkas E, Santos MA. J. Chem. Soc., Dalton Trans. 1995; 2565
    Crossref
  • 345 Nonat A, Imbert D, Pecaut J, Giraud M, Mazzanti M. Inorg. Chem. 2009; 48: 4207
    CrossrefPubMed
  • 346 Werner EJ, Avedano S, Botta M, Hay BP, Moore EG, Aime S, Raymond KN. J. Am. Chem. Soc. 2007; 129: 1870
    CrossrefPubMed
  • 347 Rohini, Baral M, Kanungo BK. New J. Chem. 2018; 42: 16040
    Crossref
  • 348 Gaspar M, Grazina R, Bodor A, Farkas E, Santos MA. J. Chem. Soc., Dalton Trans. 1999; 799
    Crossref
  • 349 Rodgers SJ, Ng CY, Raymond KN. J. Am. Chem. Soc. 1985; 107: 4094
    CrossrefPubMed
  • 350 Gaspar M, Santos MA, Krauter K, Winkelmann G. BioMetals 1999; 12: 209
    CrossrefPubMed
  • 351 Brönstrup M, Hu H, Sergeev G. WO 2016026841 A1, 2016
    PubMed
  • 352 Peukert C, Langer LN. B, Wegener SM, Tutov A, Bankstahl JP, Karge B, Bengel FM, Ross TL, Brönstrup M. J. Med. Chem. 2021; 64: 12359
    CrossrefPubMed
  • 353 Huband MD, Ito A, Tsuji M, Sader HS, Fedler A, Flamm RK. Diagn. Microbiol. Infect. Dis. 2017; 88: 198
    CrossrefPubMed
  • 354 Sato T, Yamawaki K. Clin. Infect. Dis. 2019; 69: S538
    CrossrefPubMed
  • 355 Zhanel GG, Golden AR, Zelenitsky S, Wiebe K, Lawrence CK, Adam HJ, Idowu T, Domalaon R, Schweizer F, Zhanel MA, Wiens PR. S. L, Walkty AJ, Noreddin A, Lynch JP, James II. I. Drugs 2019; 79: 271
    CrossrefPubMed