Synthesis of Carbapenems Containing Peptidoglycan Mimetics and Inhibition of the Cross-Linking Activity of a Transpeptidase of l,d Specificity.
carbapenem
esterification
peptidoglycan
peptidomimetics
transpeptidase
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
15 Feb 2021
15 Feb 2021
Historique:
received:
04
11
2020
revised:
15
12
2020
pubmed:
19
12
2020
medline:
25
2
2021
entrez:
18
12
2020
Statut:
ppublish
Résumé
The carbapenem class of β-lactams has been optimized against Gram-negative bacteria producing extended-spectrum β-lactamases by introducing substituents at position C2. Carbapenems are currently investigated for the treatment of tuberculosis as these drugs are potent covalent inhibitors of l,d-transpeptidases involved in mycobacterial cell wall assembly. The optimization of carbapenems for inactivation of these unusual targets is sought herein by exploiting the nucleophilicity of the C8 hydroxyl group to introduce chemical diversity. As β-lactams are structure analogs of peptidoglycan precursors, the substituents were chosen to increase similarity between the drug and the substrate. Fourteen peptido-carbapenems were efficiently synthesized. They were more effective than the reference drug, meropenem, owing to the positive impact of a phenethylthio substituent introduced at position C2 but the peptidomimetics added at position C8 did not further improve the activity. Thus, position C8 can be modified to modulate the pharmacokinetic properties of highly efficient carbapenems.
Identifiants
pubmed: 33336443
doi: 10.1002/chem.202004831
doi:
Substances chimiques
Anti-Bacterial Agents
0
Carbapenems
0
Peptidoglycan
0
Peptidyl Transferases
EC 2.3.2.12
Meropenem
FV9J3JU8B1
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
3542-3551Subventions
Organisme : Ministère de l'Enseignement Supérieur, de la Recherche et de l'Innovation (FR)
Informations de copyright
© 2020 Wiley-VCH GmbH.
Références
L. L. Silver, Curr. Opin. Microbiol. 2003, 6, 431-438.
S. Jovetic, Y. Zhu, G. L. Marcone, F. Marinelli, J. Tramper, Trends Biotechnol. 2010, 28, 596-604.
J. L. Mainardi, M. Fourgeaud, J. E. Hugonnet, L. Dubost, J. P. Brouard, J. Ouazzani, L. B. Rice, L. Gutmann, M. Arthur, J. Biol. Chem. 2005, 280, 38146-38152.
M. Lavollay, M. Fourgeaud, J. L. Herrmann, L. Dubost, A. Marie, L. Gutmann, M. Arthur, J. L. Mainardi, J. Bacteriol. 2011, 193, 778-782.
E. Sacco, J. E. Hugonnet, N. Josseaume, J. Cremniter, L. Dubost, A. Marie, D. Patin, D. Blanot, L. B. Rice, J. L. Mainardi, M. Arthur, Mol. Microbiol. 2010, 75, 874-885.
J. E. Hugonnet, D. Mengin-Lecreulx, A. Monton, T. den Blaauwen, E. Carbonnelle, C. Veckerle, Y. V. Brun, M. van Nieuwenhze, C. Bouchier, K. Tu, L. B. Rice, M. Arthur, Elife 2016, 5, e19469.
K. M. Papp-Wallace, A. Endimiani, M. A. Taracila, R. A. Bonomo, Antimicrob. Agents Chemother. 2011, 55, 4943-4960.
N. Bhattacharjee, S. Triboulet, V. Dubee, M. Fonvielle, Z. Edoo, J. E. Hugonnet, M. Etheve-Quelquejeu, J. P. Simorre, M. J. Field, M. Arthur, C. M. Bougault, Antimicrob. Agents Chemother. 2019, 63, e02039-18.
J. E. Hugonnet, L. W. Tremblay, H. I. Boshoff, C. E. Barry III, J. S. Blanchard, Science 2009, 323, 1215-1218.
N. Dhar, V. Dubee, L. Ballell, G. Cuinet, J. E. Hugonnet, F. Signorino-Gelo, D. Barros, M. Arthur, J. D. McKinney, Antimicrob. Agents Chemother. 2015, 59, 1308-1319.
A. H. Diacon, L. van der Merwe, M. Barnard, F. von Groote-Bidlingmaier, C. Lange, A. L. Garcia-Basteiro, E. Sevene, L. Ballell, D. Barros-Aguirre, N. Engl. J. Med. 2016, 375, 393-394.
E. Le Run, M. Arthur, J. L. Mainardi, Antimicrob. Agents Chemother. 2019, 63, e01915-18.
R. A. Floto, K. N. Olivier, L. Saiman, C. L. Daley, J. L. Herrmann, J. A. Nick, P. G. Noone, D. Bilton, P. Corris, R. L. Gibson, S. E. Hempstead, K. Koetz, K. A. Sabadosa, I. Sermet-Gaudelus, A. R. Smyth, J. van Ingen, R. J. Wallace, K. L. Winthrop, B. C. Marshall, C. S. Haworth, Thorax 2016, 71, 88-90.
M. Cordillot, V. Dubee, S. Triboulet, L. Dubost, A. Marie, J. E. Hugonnet, M. Arthur, J. L. Mainardi, Antimicrob. Agents Chemother. 2013, 57, 5940-5945.
P. Kumar, K. Arora, J. R. Lloyd, I. Y. Lee, V. Nair, E. Fischer, H. I. Boshoff, C. E. Barry III, Mol. Microbiol. 2012, 86, 367-381.
R. Gupta, M. Lavollay, J. L. Mainardi, M. Arthur, W. R. Bishai, G. Lamichhane, Nat. Med. 2010, 16, 466-469.
S. Triboulet, V. Dubee, L. Lecoq, C. Bougault, J. L. Mainardi, L. B. Rice, M. Etheve-Quelquejeu, L. Gutmann, A. Marie, L. Dubost, J. E. Hugonnet, J. P. Simorre, M. Arthur, PLoS One 2013, 8, e67831.
L. Lecoq, V. Dubee, S. Triboulet, C. Bougault, J. E. Hugonnet, M. Arthur, J. P. Simorre, ACS Chem. Biol. 2013, 8, 1140-1146.
J. L. Mainardi, J. E. Hugonnet, F. Rusconi, M. Fourgeaud, L. Dubost, A. N. Moumi, V. Delfosse, C. Mayer, L. Gutmann, L. B. Rice, M. Arthur, J. Biol. Chem. 2007, 282, 30414-30422.
D. J. Tipper, J. L. Strominger, Proc. Natl. Acad. Sci. USA 1965, 54, 1133-1141.
H. R. Josephine, I. Kumar, R. F. Pratt, J. Am. Chem. Soc. 2004, 126, 8122-8123.
M. Jamin, J. M. Wilkin, J. M. Frere, Biochemistry 1993, 32, 7278-7285.
K. H. Schleifer, O. Kandler, Bacteriol. Rev. 1972, 36, 407-477.
N. R. Silvaggi, H. R. Josephine, A. P. Kuzin, R. Nagarajan, R. F. Pratt, J. A. Kelly, J. Mol. Biol. 2005, 345, 521-533.
M. A. McDonough, J. W. Anderson, N. R. Silvaggi, R. F. Pratt, J. R. Knox, J. A. Kelly, J. Mol. Biol. 2002, 322, 111-122.
L. Dzhekieva, I. Kumar, R. F. Pratt, Biochemistry 2012, 51, 2804-2811.
H. R. Josephine, P. Charlier, C. Davies, R. A. Nicholas, R. F. Pratt, Biochemistry 2006, 45, 15873-15883.
P. H. Bentley, A. V. Stachulski, J. Chem. Soc. Perk. Trans. 1 1983, 6, 1187-1192.
S. Hanessian, C. A. Couture, N. Georgopapadakou, Bioorg. Med. Chem. Lett. 1993, 3, 2323-2328.
V. V. Nemmara, L. Dzhekieva, K. S. Sarkar, S. A. Adediran, C. Duez, R. A. Nicholas, R. F. Pratt, Biochemistry 2011, 50, 10091-10101.
E. Sauvage, A. J. Powell, J. Heilemann, H. R. Josephine, P. Charlier, C. Davies, R. F. Pratt, J. Mol. Biol. 2008, 381, 383-393.
W. Lee, M. A. McDonough, L. P. Kotra, Z. H. Li, N. R. Silvaggi, Y. Takeda, J. A. Kelly, S. Mobashery, Proc. Natl. Acad. Sci. USA 2001, 98, 1427-1431.
M. Lee, D. Hesek, M. Suvorov, W. Lee, S. Vakulenko, S. Mobashery, J. Am. Chem. Soc. 2003, 125, 16322-16326.
A. H. Berks, Tetrahedron 1996, 52, 331-375.
M. Sunagawa, A. Sasaki, J. Synth. Org. Chem. Jpn. 1996, 54, 761-771.
L. Iannazzo, D. Soroka, S. Triboulet, M. Fonvielle, F. Compain, V. Dubee, J. L. Mainardi, J. E. Hugonnet, E. Braud, M. Arthur, M. Etheve-Quelquejeu, J. Med. Chem. 2016, 59, 3427-3438.
S. S. More, R. Vince, J. Med. Chem. 2009, 52, 4650-4656.
C. P. Gordon, N. Dalton, N. Vandegraaff, J. Deadman, D. I. Rhodes, J. A. Coates, S. G. Pyne, R. Griffith, J. B. Bremner, P. A. Keller, Tetrahedron 2018, 74, 1253-1268.
T. J. Kop, J. Dordevic, M. S. Bjelakovic, D. R. Milic, Tetrahedron 2017, 73, 7073-7078.
S. B. Singh, D. Rindgen, P. Bradley, T. Suzuki, N. Wang, H. Wu, B. Zhang, L. Wang, C. Ji, H. Yu, R. M. Soll, D. B. Olsen, P. T. Meinke, D. A. Nicoll-Griffith, J. Med. Chem. 2014, 57, 8421-8444.
S. Triboulet, M. Arthur, J. L. Mainardi, C. Veckerle, V. Dubee, A. Nguekam-Moumi, L. Gutmann, L. B. Rice, J. E. Hugonnet, J. Biol. Chem. 2011, 286, 22777-22784.
Z. Edoo, M. Arthur, J. E. Hugonnet, Sci. Rep. 2017, 7, 9136.
S. Triboulet, Z. Edoo, F. Compain, C. Ourghanlian, A. Dupuis, V. Dubee, L. Sutterlin, H. Atze, M. Etheve-Quelquejeu, J. E. Hugonnet, M. Arthur, ACS Infect. Dis. 2019, 5, 1169-1176.
N. Bhattacharjee, M. J. Field, J. P. Simorre, M. Arthur, C. M. Bougault, J. Phys. Chem. B 2016, 120, 4767-4781.
P. Kuzmič, Methods Enzymol. 2009, 467, 247-280.
K. Peters, M. Pazos, Z. Edoo, J. E. Hugonnet, A. M. Martorana, A. Polissi, M. S. VanNieuwenhze, M. Arthur, W. Vollmer, Proc. Natl. Acad. Sci. USA 2018, 115, 10786-10791.
J. L. Mainardi, V. Morel, M. Fourgeaud, J. Cremniter, D. Blanot, R. Legrand, C. Frehel, M. Arthur, J. Van Heijenoort, L. Gutmann, J. Biol. Chem. 2002, 277, 35801-35807.
P. Schanda, S. Triboulet, C. Laguri, C. M. Bougault, I. Ayala, M. Callon, M. Arthur, J. P. Simorre, J. Am. Chem. Soc. 2014, 136, 17852-17860.
M. Lavollay, M. Arthur, M. Fourgeaud, L. Dubost, A. Marie, N. Veziris, D. Blanot, L. Gutmann, J. L. Mainardi, J. Bacteriol. 2008, 190, 4360-4366.
E. Le Run, M. Arthur, J. L. Mainardi, Antimicrob. Agents Chemother. 2018, 62, e00623-18.