Synthesis 2014; 46(18): 2430-2435
DOI: 10.1055/s-0033-1340193
paper
© Georg Thieme Verlag Stuttgart · New York

Fluorescent-Labeled Amino Acid–Antibiotic Conjugates

Anand D. Tiwari
a   Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA
,
Siva S. Panda*
a   Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA
,
Abdullah M. Asiri
b   Chemistry Department, King Abdulaziz University, Jeddah, 21589, Saudi Arabia
c   Center for Advanced Materials Research (CEAMR), King Abdulaziz University, Jeddah 21589, Saudi Arabia   Fax: +1(352)3929199   Email: sspanda12@gmail.com   Email: charlesdennishall@gmail.com
,
C. Dennis Hall*
a   Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA
,
Alan R. Katritzky †
a   Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA
b   Chemistry Department, King Abdulaziz University, Jeddah, 21589, Saudi Arabia
› Author Affiliations
Further Information

Publication History

Received: 31 March 2014

Accepted after revision: 01 May 2014

Publication Date:
24 June 2014 (online)


Abstract

Benzotriazole-mediated synthesis provides novel fluorescent-labeled amino acid–quinolone antibiotic conjugates in good yields with retention of chirality. The photophysical properties of all the fluorescent-labeled antibiotic conjugates were determined.

Supporting Information

 
  • References

  • 1 Chu DT. W, Plattner JJ, Katz L. J. Med. Chem. 1996; 39: 3853
  • 2 Finch R, Hunter PA. J. Antimicrob. Chemother. 2006; 58: i3
  • 3 Nikaido H, Zgurskaya HI. Curr. Opin. Infect. Dis. 1999; 12: 529
  • 4 Rice LB. Cleve. Clin. J. Med. 2007; 74: S12
  • 5 Falagas ME, Bliziotis IA. Int. J. Antimicrob. Agents 2007; 29: 630
  • 6 Davin-Regli A, Bolla JM, James CE, Lavigne JP, Chevalier J, Garnotel E, Molitor A, Pages JM. Curr. Drug Targets 2008; 9: 750
  • 7 Kascakova S, Maigre L, Chevalier J, Refregiers M, Pages JM. PLoS One 2012; 7: e38624
  • 8 Mayer A, Neuenhofer S. Angew. Chem. Int. Ed. Engl. 1994; 33: 1044
  • 9 Zimmer M. Chem. Rev. 2002; 102: 759
  • 10 Reetz MT. Angew. Chem. Int. Ed. 2001; 40: 284
  • 11 Farrer RA, Copeland GT, Previte MJ. R, Okamoto MM, Miller SJ, Fourkas JT. J. Am. Chem. Soc. 2002; 124: 1994
  • 12 Trenor SR, Shultz AR, Love BJ, Long TE. Chem. Rev. 2004; 104: 3059
  • 13 Wagner BD. Molecules 2009; 14: 210
  • 14 Paul M, Gafter-Gvili A, Fraser A, Leibovici L. Eur. J. Clin. Microbiol. Infect. Dis. 2007; 26: 825
  • 15 Sissi C, Lalumbo M. Curr. Med. Chem., Anticancer Agents 2003; 3: 439
  • 16 Sato M, Motomura T, Aramaki H, Matsuda T, Yamashita M, Yoshiharu I, Kawakami H, Matsuzaki Y, Watanabe W, Yamataka K, Ikeda S, Kodama E, Matsuoka M, Shinkai H. J. Med. Chem. 2006; 49: 1506
  • 17 Panda SS, Bajaj K, Meyers MJ, Sverdrup FM, Katritzky AR. Org. Biomol. Chem. 2012; 10: 8985
  • 18 Panda SS, Ibrahim MA, Kucukbay H, Meyers MJ, Sverdrup FM, El-Feky SA, Katritzky AR. Chem. Biol. Drug Des. 2013; 82: 361
  • 19 Ibrahim MA, Panda SS, Birs AS, Serrano JC, Gonzalaez CF, Alamry KA, Katritzky AR. Bioorg. Med. Chem. Lett. 2014; 24: 1856
  • 20 Yadav SB, Suryakar AN, Hudedar AD, Shukla PS. Ind. J. Clin. Biochem. 2006; 21: 152
  • 21 Therasse P, Arbuck SG, Eisenhauer EA, Wanders J, Kaplan RS, Rubinstein L, Verweij J, Glabbeke MV, Oosterom AT, Christian MC, Gwyther SG. J. Natl. Canc. Inst. 2000; 92: 205
  • 22 Katritzky AR, Narindoshvili T, Angrish P. Synthesis 2008; 2013
  • 23 Eckardt T, Hagen V, Schade B, Schmidt R, Schweitzer C, Bendig J. J. Org. Chem. 2002; 67: 703
  • 24 Furuta T, Wang SS.-H, Dantzker JL, Dore TM, Bybee WJ, Callaway EM, Denk W, Tsien RY. Proc. Natl. Acad. Sci. USA 1999; 96: 1193
  • 25 Biswas S, Avan I, Basak AK, Abo-Dya NE, Asiri A, Katritzky AR. Amino Acids 2013; 45: 159