7 Tetrazine-Based Cycloadditions in Click Chemistry
Buch
Herausgeber: Rutjes, F. P. J. T.
Titel: Click Chemistry
Print ISBN: 9783132435568; Online ISBN: 9783132435575; Buch-DOI: 10.1055/b000000077
1st edition © 2022. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Fachgebiete: Organische Chemie;Chemische Reaktionen, Katalyse;Organometallchemie;Chemische Labormethoden, Stöchiometrie
Science of Synthesis Reference Libraries
Übergeordnete Publikation
Titel: Science of Synthesis
DOI: 10.1055/b-00000101
Reihenherausgeber: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.
Typ: Mehrbändiges Werk
Abstract
The spontaneous cycloaddition of tetrazines with a number of different dienophiles has become a powerful tool in chemical biology, in particular for the biocompatible conjugation and modification of (bio)molecules. The exceptional reaction kinetics made these bioorthogonal ligations the methods of choice for time-critical processes at very low concentrations, facilitating controlled molecular transformations in complex environments and even in vivo. The emerging concept of bond-cleavage reactions triggered by tetrazine-based cycloadditions enabled the design of diagnostic and therapeutic strategies. The tetrazine-triggered activation of prodrugs represents the first bioorthogonal reaction performed in humans, marking the beginning of the era of clinical translation of bioorthogonal chemistry. This chapter provides an overview of the synthesis and reactivity of tetrazines, their cycloadditions with various dienophiles, and transformations triggered by these reactions, focusing on reaction mechanisms, kinetics and efficiency, and selected applications.
Schlüsselwörter
click chemistry - bioorthogonal chemistry - inverse-electron-demand Diels–Alder - dienophiles - trans-cyclooctenes - cyclooctynes - cyclopropenes - isonitriles - reaction kinetics - bioorthogonal bond-cleavage - click-to-release - tetrazines - dihydropyridazines - pyridazines - aminopyrazoles- 6 Wu K, Yee NA, Srinivasan S, Mahmoodi A, Zakharian M, Mejia Oneto JM, Royzen M. Chem. Sci.. 2021; 12: 1259
- 12 Koshy ST, Desai RM, Joly P, Li J, Bagrodia RK, Lewin SA, Joshi NS, Mooney DJ, Koshy ST, Desai RM, Li J, Bagrodia RK, Joshi NS, Mooney DJ, Koshy ST, Joly P. Adv. Healthcare Mater.. 2016; 5: 541
- 43 Stevens MFG, Hickman JA, Stone R, Gibson NW, Baig GU, Lunt E, Newton CG. J. Med. Chem.. 1984; 27: 196
- 44 Churakov AM, Ioffe SL, Strelenko YA, Tartakovskii VA. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.). 1990; 39: 639
- 58 Sauer J, Bäuerlein P, Ebenbeck W, Gousetis C, Sichert H, Troll T, Utz F, Wallfahrer U. Eur. J. Org. Chem.. 2001; 2629
- 60 Sauer J, Heldmann DK, Hetzenegger J, Krauthan J, Sichert H, Schuster J. Eur. J. Org. Chem.. 1998; 2885
- 61 Versteegen RM, Rossin R, ten Hoeve W, Janssen HM, Robillard MS. Angew. Chem. Int. Ed.. 2013; 52: 14112
- 63 Tu J, Svatunek D, Parvez S, Eckvahl HJ, Xu M, Peterson RT, Houk KN, Franzini RM. Chem. Sci.. 2020; 11: 169
- 68 Rossin R, van den Bosch SM, ten Hoeve W, Carvelli M, Versteegen RM, Lub J, Robillard MS. Bioconjugate Chem.. 2013; 24: 1210
- 69 Neves AA, Stöckmann H, Wainman YA, Kuo JC.-H, Fawcett S, Leeper FJ, Brindle KM. Bioconjugate Chem.. 2013; 24: 934
- 80 Eising S, Xin B.-T, Kleinpenning F, Heming JJA, Florea BI, Overkleeft HS, Bonger KM. ChemBioChem. 2018; 19: 1648
- 83 Rossin R, Verkerk PR, van den Bosch SM, Vulders RCM, Verel I, Lub J, Robillard MS. Angew. Chem. Int. Ed.. 2010; 49: 3375
- 85 Sarris AJC, Hansen T, de Geus MAR, Maurits E, Doelman W, Overkleeft HS, Codée JDC, Filippov DV, van Kasteren SI. Chem.–Eur. J.. 2018; 24: 18075
- 86 Fan X, Ge Y, Lin F, Yang Y, Zhang G, Ngai WSC, Lin Z, Zheng S, Wang J, Zhao J, Li J, Chen PR. Angew. Chem. Int. Ed.. 2016; 55: 14046
- 89 Darko A, Wallace S, Dmitrenko O, Machovina MM, Mehl RA, Chin JW, Fox JM. Chem. Sci.. 2014; 5: 3770
- 91 Tu J, Svatunek D, Parvez S, Liu AC, Levandowski BJ, Eckvahl HJ, Peterson RT, Houk KN, Franzini RM. Angew. Chem. Int. Ed.. 2019; 58: 9043
- 97 Audebert P, Sadki S, Miomandre F, Clavier G, Vernières MC, Saoud M, Hapiot P. New J. Chem.. 2004; 28: 387
- 100 McGrane SD, Bolme CA, Greenfield MT, Chavez DE, Hanson SK, Scharff RJ. J. Phys. Chem. A. 2016; 120: 895
- 102 Tolshchina SG, Rusinov GL, Charushin VN. Chem. Heterocycl. Compd. (N. Y., NY, U. S.). 2013; 49: 66
- 104 Quinton C, Alain-Rizzo V, Dumas-Verdes C, Clavier G, Vignau L, Audebert P. New J. Chem.. 2015; 39: 9700
- 111 Lambert WD, Fang Y, Mahapatra S, Huang Z, am Ende CW, Fox JM. J. Am. Chem. Soc.. 2019; 141: 17068
- 116 Qu Y, Pander P, Vybornyi O, Vasylieva M, Guillot R, Miomandre F, Dias FB, Skabara P, Data P, Clavier G, Audebert P. J. Org. Chem.. 2020; 85: 3407
- 120 Blizzard RJ, Backus DR, Brown W, Bazewicz CG, Li Y, Mehl RA. J. Am. Chem. Soc.. 2015; 137: 10044
- 125 Hoffmann J.-E, Plass T, Nikić I, Aramburu IV, Koehler C, Gillandt H, Lemke EA, Schultz C. Chem.–Eur. J.. 2015; 21: 12266
- 126 Murrey HE, Judkins JC, am Ende CW, Ballard TE, Fang Y, Riccardi K, Di L, Guilmette ER, Schwartz JW, Fox JM, Johnson DS. J. Am. Chem. Soc.. 2015; 137: 11461
- 136 Svatunek D, Denk C, Rosecker V, Sohr B, Hametner C, Allmaier G, Fröhlich J, Mikula H. Monatsh. Chem.. 2016; 147: 579
- 139 Wilkovitsch M, Haider M, Sohr B, Herrmann B, Klubnick J, Weissleder R, Carlson JCT, Mikula H. J. Am. Chem. Soc.. 2020; 142: 19132
- 141 Vázquez A, Dzijak R, Dračínský M, Rampmaier R, Siegl SJ, Vrabel M. Angew. Chem. Int. Ed.. 2017; 56: 1334
- 142 Dommerholt J, Schmidt S, Temming R, Hendriks LJA, Rutjes FPJT, van Hest JCM, Lefeber DJ, Friedl P, van Delft FL. Angew. Chem. Int. Ed.. 2010; 49: 9422
- 144 Wang M, Svatunek D, Rohlfing K, Liu Y, Wang H, Giglio B, Yuan H, Wu Z, Li Z, Fox J. Theranostics. 2016; 6: 887
- 145 Seitchik JL, Peeler JC, Taylor MT, Blackman ML, Rhoads TW, Cooley RB, Refakis C, Fox JM, Mehl RA. J. Am. Chem. Soc.. 2012; 134: 2898
- 147 Kozma E, Nikić I, Varga BR, Aramburu IV, Kang JH, Fackler OT, Lemke EA, Kele P. ChemBioChem. 2016; 17: 1518
- 148 Siegl SJ, Vázquez A, Dzijak R, Dračínský M, Galeta J, Rampmaier R, Klepetářová B, Vrabel M. Chem.–Eur. J.. 2018; 24: 2426
- 151 Lambert WD, Scinto SL, Dmitrenko O, Boyd SJ, Magboo R, Mehl RA, Chin JW, Fox JM, Wallace S. Org. Biomol. Chem.. 2017; 15: 6640
- 152 Wang M, Vannam R, Lambert WD, Xie Y, Wang H, Giglio B, Ma X, Wu Z, Fox J, Li Z. Chem. Commun. (Cambridge). 2019; 55: 2485
- 153 Pigga JE, Rosenberger JE, Jemas A, Boyd SJ, Dmitrenko O, Xie Y, Fox JM. Angew. Chem. Int. Ed.. 2021; 60: 14975
- 155 Krebs A, Pforr K.-I, Raffay W, Thölke B, König WA, Hardt I, Boese R. Angew. Chem. Int. Ed. Engl.. 1997; 36: 159
- 162 Fang Y, Zhang H, Huang Z, Scinto SL, Yang JC, am Ende CW, Dmitrenko O, Johnson DS, Fox JM. Chem. Sci.. 2018; 9: 1953
- 163 Cioslowski J, Sauer J, Hetzenegger J, Karcher T, Hierstetter T. J. Am. Chem. Soc.. 1993; 115: 1353
- 167 Debets MF, van Berkel SS, Schoffelen S, Rutjes FPJT, van Hest JCM, van Delft FL. Chem. Commun. (Cambridge). 2010; 46: 97
- 173 Lang K, Davis L, Wallace S, Mahesh M, Cox DJ, Blackman ML, Fox JM, Chin JW. J. Am. Chem. Soc.. 2012; 134: 10317
- 174 Pinto-Pacheco B, Carbery WP, Khan S, Turner DB, Buccella D. Angew. Chem. Int. Ed.. 2020; 59: 22140
- 178 Vrabel M, Kölle P, Brunner KM, Gattner MJ, López-Carrillo V, de Vivie-Riedle R, Carell T. Chem.–Eur. J.. 2013; 19: 13309
- 182 Nikić I, Plass T, Schraidt O, Szymański J, Briggs JAG, Schultz C, Lemke EA. Angew. Chem. Int. Ed.. 2014; 53: 2245
- 183 Matikonda SS, Orsi DL, Staudacher V, Jenkins IA, Fiedler F, Chen J, Gamble AB. Chem. Sci.. 2015; 6: 1212
- 187 Matsuura M, Saikawa Y, Inui K, Nakae K, Igarashi M, Hashimoto K, Nakata M. Nat. Chem. Biol.. 2009; 5: 465
- 192 Späte A.-K, Bußkamp H, Niederwieser A, Schart VF, Marx A, Wittmann V. Bioconjugate Chem.. 2014; 25: 147
- 193 Elliott TS, Townsley FM, Bianco A, Ernst RJ, Sachdeva A, Elsässer SJ, Davis L, Lang K, Pisa R, Greiss S, Lilley KS, Chin JW. Nat. Biotechnol.. 2014; 32: 465
- 194 Xiong D.-C, Zhu J, Han M.-J, Luo H.-X, Wang C, Yu Y, Ye Y, Tai G, Ye X.-S. Org. Biomol. Chem.. 2015; 13: 3911
- 195 Kamber DN, Nazarova LA, Liang Y, Lopez SA, Patterson DM, Shih H.-W, Houk KN, Prescher JA. J. Am. Chem. Soc.. 2013; 135: 13680
- 203 Yamada T, Yanagi T, Omote Y, Miyazawa T, Kuwata S, Sugiura M, Matsumoto K. J. Chem. Soc., Chem. Commun.. 1990; 1640
- 205 Stairs S, Neves AA, Stöckmann H, Wainman YA, Ireland-Zecchini H, Brindle KM, Leeper FJ. ChemBioChem. 2013; 14: 1063
- 207 Wainman YA, Neves AA, Stairs S, Stöckmann H, Ireland-Zecchini H, Brindle KM, Leeper FJ. Org. Biomol. Chem.. 2013; 11: 7297
- 209 Braun K, Wiessler M, Ehemann V, Pipkorn R, Spring H, Debus J, Didinger B, Koch M, Muller G, Waldeck W. Drug Des., Dev. Ther.. 2008; 2: 289
- 211 Niederwieser A, Späte A.-K, Nguyen LD, Jüngst C, Reutter W, Wittmann V. Angew. Chem. Int. Ed.. 2013; 52: 4265
- 212 Bußkamp H, Batroff E, Niederwieser A, Abdel-Rahman OS, Winter RF, Wittmann V, Marx A. Chem. Commun. (Cambridge). 2014; 50: 10827
- 213 Lee Y.-J, Kurra Y, Yang Y, Torres-Kolbus J, Deiters A, Liu WR. Chem. Commun. (Cambridge). 2014; 50: 13085
- 222 Kiesewetter ET, OʼBrien RV, Yu EC, Meek SJ, Schrock RR, Hoveyda AH. J. Am. Chem. Soc.. 2013; 135: 6026
- 223 Barbeyron R, Benedetti E, Cossy J, Vasseur J.-J, Arseniyadis S, Smietana M. Tetrahedron. 2014; 70: 8431
- 227 Zhang H, Trout WS, Liu S, Andrade GA, Hudson DA, Scinto SL, Dicker KT, Li Y, Lazouski N, Rosenthal J, Thorpe C, Jia X, Fox JM. J. Am. Chem. Soc.. 2016; 138: 5978
- 228 Wang C, Zhang H, Zhang T, Zou X, Wang H, Rosenberger JE, Vannam R, Trout WS, Grimm JB, Lavis LD, Thorpe C, Jia X, Li Z, Fox JM. J. Am. Chem. Soc.. 2021; 143: 10793
- 229 Kumar P, Zainul O, Camarda FM, Jiang T, Mannone JA, Huang W, Laughlin ST. Org. Lett.. 2019; 21: 3721
- 231 Mayer SV, Murnauer A, von Wrisberg M.-K, Jokisch M.-L, Lang K. Angew. Chem. Int. Ed.. 2019; 58: 15876
- 232 Rossin R, van Duijnhoven SMJ, ten Hoeve W, Janssen HM, Kleijn LHJ, Hoeben FJM, Versteegen RM, Robillard MS. Bioconjugate Chem.. 2016; 27: 1697
- 233 Rossin R, Versteegen RM, Wu J, Khasanov A, Wessels HJ, Steenbergen EJ, ten Hoeve W, Janssen HM, van Onzen AHAM, Hudson PJ, Robillard MS. Nat. Commun.. 2018; 9: 1484
- 234 van Onzen AHAM, Versteegen RM, Hoeben FJM, Filot IAW, Rossin R, Zhu T, Wu J, Hudson PJ, Janssen HM, ten Hoeve W, Robillard MS. J. Am. Chem. Soc.. 2020; 142: 10955
- 236 Czuban M, Srinivasan S, Yee NA, Agustin E, Koliszak A, Miller E, Khan I, Quinones I, Noory H, Motola C, Volkmer R, Di Luca M, Trampuz A, Royzen M, Mejia Oneto JM. ACS Cent. Sci.. 2018; 4: 1624
- 237 Srinivasan S, Yee NA, Wu K, Zakharian M, Mahmoodi A, Royzen M, Mejia Oneto JM. Adv. Ther. (Weinheim, Ger.). 2021; 4: 2000 243
- 242 Jiménez-Moreno E, Guo Z, Oliveira BL, Albuquerque IS, Kitowski A, Guerreiro A, Boutureira O, Rodrigues T, Jiménez-Osés G, Bernardes GJL. Angew. Chem. Int. Ed.. 2017; 56: 243
- 244 Versteegen RM, ten Hoeve W, Rossin R, de Geus MAR, Janssen HM, Robillard MS. Angew. Chem. Int. Ed.. 2018; 57: 10494
- 252 Neumann K, Jain S, Gambardella A, Walker SE, Valero E, Lilienkampf A, Bradley M. ChemBioChem. 2017; 18: 91
- 260 Selvaraj R, Liu S, Hassink M, Huang C.-w, Yap L.-p, Park R, Fox JM, Li Z, Conti PS. Bioorg. Med. Chem. Lett.. 2011; 21: 5011
- 262 Zeglis BM, Sevak KK, Reiner T, Mohindra P, Carlin SD, Zanzonico P, Weissleder R, Lewis JS. J. Nucl. Med.. 2013; 54: 1389
- 263 Rossin R, van Duijnhoven SMJ, Läppchen T, van den Bosch SM, Robillard MS. Mol. Pharmaceutics. 2014; 11: 3090
- 264 van Duijnhoven SMJ, Rossin R, van den Bosch SM, Wheatcroft MP, Hudson PJ, Robillard MS. J. Nucl. Med.. 2015; 56: 1422
- 265 Denk C, Svatunek D, Mairinger S, Stanek J, Filip T, Matscheko D, Kuntner C, Wanek T, Mikula H. Bioconjugate Chem.. 2016; 27: 1707
- 266 Denk C, Svatunek D, Filip T, Wanek T, Lumpi D, Fröhlich J, Kuntner C, Mikula H. Angew. Chem. Int. Ed.. 2014; 53: 9655
- 267 Denk C, Wilkovitsch M, Aneheim E, Herth MM, Jensen H, Lindegren S, Mikula H. ChemPlusChem. 2019; 84: 775
- 268 Stéen EJL, Jørgensen JT, Denk C, Battisti UM, Nørregaard K, Edem PE, Bratteby K, Shalgunov V, Wilkovitsch M, Svatunek D, Poulie CBM, Hvass L, Simón M, Wanek T, Rossin R, Robillard M, Kristensen JL, Mikula H, Kjaer A, Herth MM. ACS Pharmacol. Transl. Sci.. 2021; 4: 824
- 269 García-Vázquez R, Battisti UM, Jørgensen JT, Shalgunov V, Hvass L, Stares DL, Petersen IN, Crestey F, Löffler A, Svatunek D, Kristensen JL, Mikula H, Kjaer A, Herth MM. Chem. Sci.. 2021; 12: 11668
- 270 Meyer J.-P, Houghton JL, Kozlowski P, Abdel-Atti D, Reiner T, Pillarsetty NV, Scholz WW, Zeglis BM, Lewis JS. Bioconjugate Chem.. 2016; 27: 298
- 272 Houghton JL, Membreno R, Abdel-Atti D, Cunanan KM, Carlin S, Scholz WW, Zanzonico PB, Lewis JS, Zeglis BM. Mol. Cancer Ther.. 2017; 16: 124
- 277 Plass T, Milles S, Koehler C, Szymański J, Mueller R, Wiessler M, Schultz C, Lemke EA. Angew. Chem. Int. Ed.. 2012; 51: 4166
- 279 Meimetis LG, Carlson JCT, Giedt RJ, Kohler RH, Weissleder R. Angew. Chem. Int. Ed.. 2014; 53: 7531
- 280 Werther P, Yserentant K, Braun F, Kaltwasser N, Popp C, Baalmann M, Herten D.-P, Wombacher R. Angew. Chem. Int. Ed.. 2020; 59: 804
- 282 Werther P, Yserentant K, Braun F, Grußmayer K, Navikas V, Yu M, Zhang Z, Ziegler MJ, Mayer C, Gralak AJ, Busch M, Chi W, Rominger F, Radenovic A, Liu X, Lemke EA, Buckup T, Herten D.-P, Wombacher R. ACS Cent. Sci.. 2021; 7: 1561
- 283 Siegl SJ, Galeta J, Dzijak R, Vázquez A, Del Río-Villanueva M, Dračínský M, Vrabel M. ChemBioChem. 2019; 20: 886