Ligand-Directed Modification of Active Matrix Metalloproteases: Activity-based Probes with no Photolabile Group.
activity-based probes
affinity-labelling
ligand-directed chemistry
macrophage elastase
metalloproteases
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
09 08 2021
09 08 2021
Historique:
received:
06
05
2021
pubmed:
8
6
2021
medline:
8
6
2021
entrez:
7
6
2021
Statut:
ppublish
Résumé
Activity-based probes enable discrimination between the active enzyme and its inactive or inactivated counterparts. Since metalloproteases catalysis is non-covalent, activity-based probes targeting them have been systematically developed by decorating reversible inhibitors with photo-crosslinkers. By exploiting two types of ligand-guided chemistry, we identified novel activity-based probes capable of covalently modifying the active site of matrix metalloproteases (MMPs) without any external trigger. The ability of these probes to label recombinant MMPs was validated in vitro and the identity of the main labelling sites within their S
Identifiants
pubmed: 34096148
doi: 10.1002/anie.202106117
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
18272-18279Informations de copyright
© 2021 Wiley-VCH GmbH.
Références
T. Klein, U. Eckhard, A. Dufour, N. Solis, C. M. Overall, Chem. Rev. 2018, 118, 1137-1168.
R. E. Vandenbroucke, C. Libert, Nat. Rev. Drug Discovery 2014, 13, 904-927.
P. G. Jobin, G. S. Butler, C. M. Overall, Biochim. Biophys. Acta Mol. Cell Res. 2017, 1864, 2043-2055.
D. J. Marchant, C. L. Bellac, T. J. Moraes, S. J. Wadsworth, A. Dufour, G. S. Butler, L. M. Bilawchuk, R. G. Hendry, A. G. Robertson, C. T. Cheung, J. Ng, L. Ang, Z. Luo, K. Heilbron, M. J. Norris, W. Duan, T. Bucyk, A. Karpov, L. Devel, D. Georgiadis, R. G. Hegele, H. Luo, D. J. Granville, V. Dive, B. M. McManus, C. M. Overall, Nat. Med. 2014, 20, 493-502.
C. M. Overall, O. Kleifeld, Nat. Rev. Cancer 2006, 6, 227-239.
L. M. Coussens, B. Fingleton, L. M. Matrisian, Science 2002, 295, 2387-2392.
M. Vizovišek, R. Vidmar, M. Drag, M. Fonović, G. S. Salvesen, B. Turk, Trends Biochem. Sci. 2018, 43, 829-844.
M. Verdoes, S. H. L. Verhelst, Biochim. Biophys. Acta Proteins Proteomics 2016, 1864, 130-142.
R. L. Scherer, J. O. McIntyre, L. M. Matrisian, Cancer Metastasis Rev. 2008, 27, 679-690.
L. Zhu, J. Xie, M. Swierczewska, F. Zhang, Q. Quan, Y. Ma, X. Fang, K. Kim, S. Lee, X. Chen, Theranostics 2011, 1, 18-27.
S. Chakrabarty, J. P. Kahler, M. A. T. van de Plassche, R. Vanhoutte, S. H. L. Verhelst, Curr. Top. Microbiol. Immunol. 2019, 420, 253-281.
L. I. Willems, H. S. Overkleeft, S. I. van Kasteren, Bioconjugate Chem. 2014, 25, 1181-1191.
S. Serim, U. Haedke, S. H. L. Verhelst, ChemMedChem 2012, 7, 1146-1159.
E. Deu, M. Verdoes, M. Bogyo, Nat. Struct. Mol. Biol. 2012, 19, 9-16.
A. Saghatelian, N. Jessani, A. Joseph, M. Humphrey, B. F. Cravatt, Proc. Natl. Acad. Sci. USA 2004, 101, 10000-10005.
E. W. S. Chan, S. Chattopadhaya, R. C. Panicker, X. Huang, S. Q. Yao, J. Am. Chem. Soc. 2004, 126, 14435-14446.
S. A. Sieber, S. Niessen, H. S. Hoover, B. F. Cravatt, Nat. Chem. Biol. 2006, 2, 274-281.
M. A. Leeuwenburgh, P. P. Geurink, T. Klein, H. F. Kauffman, G. A. van der Marel, R. Bischoff, H. S. Overkleeft, Org. Lett. 2006, 8, 1705-1708.
J. Wang, M. Uttamchandani, J. Li, M. Hu, S. Q. Yao, Org. Lett. 2006, 8, 3821-3824.
A. David, D. Steer, S. Bregant, L. Devel, A. Makaritis, F. Beau, A. Yiotakis, V. Dive, Angew. Chem. Int. Ed. 2007, 46, 3275-3277;
Angew. Chem. 2007, 119, 3339-3341.
P. P. Geurink, L. M. Prely, G. A. van der Marel, R. Bischoff, H. S. Overkleeft, Top. Curr. Chem. 2012, 324, 85-113.
S. Bregant, C. Huillet, L. Devel, A.-S. Dabert-Gay, F. Beau, R. Thai, B. Czarny, A. Yiotakis, V. Dive, J. Proteome Res. 2009, 8, 2484-2494.
C. Nury, B. Czarny, E. Cassar-Lajeunesse, D. Georgiadis, S. Bregant, V. Dive, ChemBioChem 2013, 14, 107-114.
L. Prely, T. Klein, P. P. Geurink, K. Paal, H. S. Overkleeft, R. Bischoff, Methods Mol. Biol. 2017, 1491, 103-111.
K. C. Ravindra, C. C. Ahrens, Y. Wang, J. Y. Ramseier, J. S. Wishnok, L. G. Griffith, A. J. Grodzinsky, S. R. Tannenbaum, J. Biol. Chem. 2018, 293, 11459-11469.
C. C. Ahrens, E. L. Chiswick, K. C. Ravindra, M. A. Miller, J. Y. Ramseier, K. B. Isaacson, D. A. Lauffenburger, L. G. Griffith, Biochemistry 2019, 58, 3938-3942.
Q. Zhu, A. Girish, S. Chattopadhaya, S. Q. Yao, Chem. Commun. 2004, 1512-1513.
S. A. Testero, C. Granados, D. Fernández, P. Gallego, G. Covaleda, D. Reverter, J. Vendrell, F. X. Avilés, I. Pallarès, S. Mobashery, ACS Med. Chem. Lett. 2017, 8, 1122-1127.
C. Forbes, Q. Shi, J. F. Fisher, M. Lee, D. Hesek, L. I. Llarrull, M. Toth, M. Gossing, R. Fridman, S. Mobashery, Chem. Biol. Drug Des. 2009, 74, 527-534.
M. Morell, T. Nguyen Duc, A. L. Willis, S. Syed, J. Lee, E. Deu, Y. Deng, J. Xiao, B. E. Turk, J. R. Jessen, S. J. Weiss, M. Bogyo, J. Am. Chem. Soc. 2013, 135, 9139-9148.
N. Amara, M. Tholen, M. Bogyo, ACS Chem. Biol. 2018, 13, 2645-2654.
T. Tamura, I. Hamachi, J. Am. Chem. Soc. 2019, 141, 2782-2799.
L. Devel, V. Rogakos, A. David, A. Makaritis, F. Beau, P. Cuniasse, A. Yiotakis, V. Dive, J. Biol. Chem. 2006, 281, 11152-11160.
B. Czarny, E. A. Stura, L. Devel, L. Vera, E. Cassar-Lajeunesse, F. Beau, V. Calderone, M. Fragai, C. Luchinat, V. Dive, J. Med. Chem. 2013, 56, 1149-1159.
S. Fujishima, R. Yasui, T. Miki, A. Ojida, I. Hamachi, J. Am. Chem. Soc. 2012, 134, 3961-3964.
K. Yamaura, S. Kiyonaka, T. Numata, R. Inoue, I. Hamachi, Nat. Chem. Biol. 2016, 12, 822-830.
S. Wakayama, S. Kiyonaka, I. Arai, W. Kakegawa, S. Matsuda, K. Ibata, Y. L. Nemoto, A. Kusumi, M. Yuzaki, I. Hamachi, Nat. Commun. 2017, 8, 14850.
T. Tamura, T. Ueda, T. Goto, T. Tsukidate, Y. Shapira, Y. Nishikawa, A. Fujisawa, I. Hamachi, Nat. Commun. 2018, 9, 1870.
A.-S. Dabert-Gay, B. Czarny, L. Devel, F. Beau, E. Lajeunesse, S. Bregant, R. Thai, A. Yiotakis, V. Dive, J. Biol. Chem. 2008, 283, 31058-31067.
T. Ueda, T. Tamura, M. Kawano, K. Shiono, F. Hobor, A. J. Wilson, I. Hamachi, J. Am. Chem. Soc. 2021, 143, 4766-4774.
R. Visse, H. Nagase, Circ. Res. 2003, 92, 827-839.
H. Laronha, J. Caldeira, Cells 2020, 9, 1076.
C. Nury, S. Bregant, B. Czarny, F. Berthon, E. Cassar-Lajeunesse, V. Dive, J. Biol. Chem. 2013, 288, 5636-5644.
C. Rouanet-Mehouas, B. Czarny, F. Beau, E. Cassar-Lajeunesse, E. A. Stura, V. Dive, L. Devel, J. Med. Chem. 2017, 60, 403-414.