In Silico Design and Enantioselective Synthesis of Functionalized Monocyclic 3-Amino-1-carboxymethyl-β-lactams as Inhibitors of Penicillin-Binding Proteins of Resistant Bacteria.
[en] As a complement to the renowned bicyclic β-lactam antibiotics, monocyclic analogues provide a breath of fresh air in the battle against resistant bacteria. In that framework, the present study discloses the in silico design and unprecedented ten-step synthesis of eleven nocardicin-like enantiomerically pure 2-{3-[2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-2-oxoazetidin-1-yl}acetic acids starting from serine as a readily accessible precursor. The capability of this novel class of monocyclic 3-amino-β-lactams to inhibit penicillin-binding proteins (PBPs) of various (resistant) bacteria was assessed, revealing the potential of α-benzylidenecarboxylates as interesting leads in the pursuit of novel PBP inhibitors. No deactivation by representative enzymes belonging to the four β-lactamase classes was observed, while weak inhibition of class C β-lactamase P99 was demonstrated.
Disciplines :
Biochemistry, biophysics & molecular biology
Author, co-author :
Decuyper, Lena ; SynBioC Research Group, Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000, Ghent, Belgium
Deketelaere, Sari ; SynBioC Research Group, Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000, Ghent, Belgium
Vanparys, Lore; SynBioC Research Group, Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000, Ghent, Belgium
Jukič, Marko ; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Ljubljana, Aškerčeva 7, 1000, Ljubljana, Slovenia
Sosič, Izidor ; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Ljubljana, Aškerčeva 7, 1000, Ljubljana, Slovenia
Sauvage, Eric ; Université de Liège - ULiège > Département des sciences de la vie
Amoroso, Ana Maria ; Université de Liège - ULiège > Integrative Biological Sciences (InBioS)
Verlaine, Olivier ; Université de Liège - ULiège > Département des sciences de la vie > Centre d'Ingénierie des Protéines (CIP)
Joris, Bernard ; Université de Liège - ULiège > Integrative Biological Sciences (InBioS)
Gobec, Stanislav ; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Ljubljana, Aškerčeva 7, 1000, Ljubljana, Slovenia
D'hooghe, Matthias ; SynBioC Research Group, Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000, Ghent, Belgium
Language :
English
Title :
In Silico Design and Enantioselective Synthesis of Functionalized Monocyclic 3-Amino-1-carboxymethyl-β-lactams as Inhibitors of Penicillin-Binding Proteins of Resistant Bacteria.
FWO - Research Foundation Flanders Slovenian Research Agency BELSPO - Belgian Federal Science Policy Office
Funding text :
The authors are indebted to the Research Foundation—Flanders (FWO), the Slovenian Research Agency (project L1-6745) and Belspo IAP-Project P44-iPros for financial support. Special thanks are devoted to Asst. Prof. Marija Gencˇić of the University of Nisˇ, Serbia, for the help with the energy-minimization calculations and NOESY experiments and analysis thereof.The authors are indebted to the Research Foundation—Flanders (FWO), the Slovenian Research Agency (project L1-6745) and Belspo IAP-Project P44-iPros for financial support. Special thanks are devoted to Asst. Prof. Marija Genčić of the University of Niš, Serbia, for the help with the energy-minimization calculations and NOESY experiments and analysis thereof.
scite shows how a scientific paper has been cited by providing the context of the citation, a classification describing whether it supports, mentions, or contrasts the cited claim, and a label indicating in which section the citation was made.
Bibliography
W. Vollmer, D. Blanot, M. A. De Pedro, FEMS Microbiol. Rev. 2008, 32, 149–167
D. J. Tipper, J. L. Strominger, Proc. Natl. Acad. Sci. USA 1965, 54, 1133–1141
N. Georgopapadakou, S. Hammarstrom, J. L. Strominger, Proc. Natl. Acad. Sci. USA 1977, 74, 1009–1012
P. Macheboeuf, C. Contreras-Martel, V. Job, O. Dideberg, A. Dessen, FEMS Microbiol. Rev. 2006, 30, 673–691
M. Bassetti, M. Merelli, C. Temperoni, A. Astilean, Ann. Clin. Microbiol. Antimicrob. 2013, 12, 22
S. M. Drawz, R. A. Bonomo, Clin. Microbiol. Rev. 2010, 23, 160–201
A. Zapun, C. Contreras-Martel, T. Vernet, FEMS Microbiol. Rev. 2008, 32, 361–385
L. Decuyper, M. Jukič, I. Sosič, A. Žula, M. D′hooghe, S. Gobec, Med. Res. Rev. 2018, 38, 426–503
G. S. Singh, Mini-Rev. Med. Chem. 2004, 4, 69–92
R. B. Sykes, D. P. Bonner, Am. J. Med. 1985, 78, 2–10
H. Aoki, H. Sakai, M. Kohsaka, T. Konomi, J. Hosoda, J. Antibiot. 1976, 29, 492–500
D. P. Bonner, R. B. Sykes, J. Antimicrob. Chemother. 1984, 14, 313–327
J. C. Dobrowolski, J. Sadlej, A. P. Mazulrek, J. Mol. Struct. 2003, 638, 229–234
E. Sauvage, unpublished work, 2018
C. A. Townsend, G. M. Salituro, L. T. Nguyen, M. J. DiNovi, Tetrahedron Lett. 1986, 27, 3819–3822
H.-Y. Kang, A. N. Pae, H. Y. Koh, M. H. Chang, Bull. Korean Chem. Soc. 1991, 12, 75–79
O. Nakaguchi, T. Oku, H. Takeno, M. Hashimoto, T. Kamiya, Chem. Pharm. Bull. 1987, 35, 3985–3994
G. H. Hakimelahi, S.-C. Tsay, J. R. Hwu, Helv. Chim. Acta 1995, 78, 411–420
M. J. Miller, P. G. Mattingly, M. A. Morrison, J. F. Kerwin, J. Am. Chem. Soc. 1980, 102, 7026–7032
L. E. Overman, T. Osawa, J. Am. Chem. Soc. 1985, 107, 1698–1701
S. Deketelaere, T. V. Nguyen, C. V. Stevens, M. D′hooghe, ChemistryOpen 2017, 6, 301–319
J. Bayardon, D. Sinou, Tetrahedron: Asymmetry 2005, 16, 2965–2972
R. I. Higuchi, T. C. Roberts, P. A. Smith, D. Campbell, P. Paraselli, PCT Int. Appl. WO 2013123456A1, 2013
A. Sliwa, G. Dive, J.-L. H. Jiwan, J. Marchand-Brynaert, Tetrahedron 2010, 66, 9519–9527
O. Mitsunobu, M. Yamada, Bull. Chem. Soc. Jpn. 1967, 40, 2380–2382
G. Papageorgiou, D. Ogden, J. E. T. Corrie, J. Org. Chem. 2004, 69, 7228–7233
H. Wild, W. Hartwig, Synthesis 1992, 1099–1103
H. Mastalerz, M. Menard, V. Vinet, J. Desiderio, J. Fung-Tomc, R. Kessler, Y. Tsai, J. Med. Chem. 1988, 31, 1190–1196
O. Sakurai, H. Horikawa, T. Iwasaki, J. Chem. Soc. Chem. Commun. 1995, 2527–2528
I. Ojima, T. Komata, X. Qiu, J. Am. Chem. Soc. 1990, 112, 770–774
V. N. Yandovskii, B. V. Gidaspov, I. V. Tselinskii, Russ. Chem. Rev. 1980, 49, 237–248
R. A. Moss, Acc. Chem. Res. 1974, 7, 421–427
M. F. Brown, M. J. Mitton-Fry, J. T. Arcari, R. Barham, J. Casavant, B. S. Gerstenberger, S. Han, J. R. Hardink, T. M. Harris, T. Hoang, M. D. Huband, M. S. Lall, M. M. Lemmon, C. Li, J. Lin, S. P. McCurdy, E. McElroy, E. McPherson, E. S. Marr, J. P. Mueller, L. Mullins, A. A. Nikitenko, M. C. Noe, J. Penzien, M. S. Plummer, B. P. Schuff, V. Shanmugasundaram, J. T. Starr, J. Sun, A. Tomaras, J. A. Young, R. P. Zaniewski, J. Med. Chem. 2013, 56, 5541–5552
J. Liu, Q. Liu, X. Yang, S. Xu, H. Zhang, R. Bai, H. Yao, J. Jiang, M. Shen, X. Wu, J. Xu, Bioorg. Med. Chem. 2013, 21, 7742–7751
J. W. Fisher, K. L. Trinkle, Tetrahedron Lett. 1994, 35, 2505–2508
P. D. G. Dean, J. Chem. Soc. 1965, 6655
E. Biron, H. Kessler, J. Org. Chem. 2005, 70, 5183–5189
D. Nasipuri, Stereochemistry of Organic Compounds: Principles and Applications, 2nd ed., New Age International, New Delhi, 1994
R. Lacret, I. Pérez-Victoria, D. Oves-Costales, M. de la Cruz, E. Domingo, J. Martin, C. Diaz, F. Vicente, O. Genilloud, F. Reyes, Mar. Drugs 2016, 14, 188
S.-P. Yang, J.-G. Cheng, J. Huo, H.-L. Jiang, K.-X. Chen, J.-M. Yue, Chin. J. Chem. 2005, 23, 1530–1536
W. M. Zin, S. Buttachon, T. Dethoup, C. Fernandes, S. Cravo, M. M. M. Pinto, L. Gales, J. A. Pereira, A. M. S. Silva, N. Sekeroglu, A. Kijjoa, Mar. Drugs 2016, 14, 136
S. M. Ali, S. Khan, G. Crowyn, Magn. Reson. Chem. 2012, 50, 299–304
G. A. Molander, F. Cadoret, Tetrahedron Lett. 2011, 52, 2199–2202
P. M. Nair, J. D. Roberts, J. Am. Chem. Soc. 1957, 79, 4565–4566
E. R. Kennedy, R. S. Macomber, J. Org. Chem. 1974, 39, 1952–1955
E. Harder, W. Damm, J. Maple, C. Wu, M. Reboul, J. Y. Xiang, L. Wang, D. Lupyan, M. K. Dahlgren, J. L. Knight, J. W. Kaus, D. S. Cerutti, G. Krilov, W. L. Jorgensen, R. Abel, R. A. Friesner, J. Chem. Theory Comput. 2016, 12, 281–296
A. D. Bochevarov, E. Harder, T. F. Hughes, J. R. Greenwood, D. A. Braden, D. M. Philipp, D. Rinaldo, M. D. Halls, J. Zhang, R. A. Friesner, Int. J. Quantum Chem. 2013, 113, 2110–2142
E. Sauvage, A. Derouaux, C. Fraipont, M. Joris, R. Herman, M. Rocaboy, M. Schloesser, J. Dumas, F. Kerff, M. Nguyen-Distèche, P. Charlier, PLoS One 2014, 9, e98042
E. Sauvage, F. Kerff, E. Fonzé, R. Herman, B. Schoot, J.-P. Marquette, Y. Taburet, D. Prevost, J. Dumas, G. Leonard, P. Stefanic, J. Coyette, P. Charlier, Cell. Mol. Life Sci. 2002, 59, 1223–1232
B. Granier, M. Jamin, M. Adam, M. Galleni, B. Lakaye, W. Zorzi, J. Grandchamps, J. M. Wilkin, C. Fraipont, B. Joris, C. Duez, M. Nguyendisteche, J. Coyette, M. Leyhbouille, J. Dusart, L. Christiaens, J. M. Frere, J. M. Ghuysen, Methods Enzymol. 1994, 244, 249–266
G. Zhao, T. I. Meier, S. D. Kahl, K. R. Gee, L. C. Blaszczak, Antimicrob. Agents Chemother. 1999, 43, 1124–1128
B. Lakaye, C. Damblon, M. Jamin, M. Galleni, S. Lepage, B. Joris, J. Marchand-Brynaert, C. Frydrych, J. M. Frere, Biochem. J. 1994, 300, 141–145
S. Turk, O. Verlaine, T. Gerards, M. Zivec, J. Humljan, I. Sosic, A. M. Amoroso, A. Zervosen, A. Luxen, B. Joris, S. Gobec, PLoS One 2011, 6, e19418
O. Kocaoglu, E. E. Carlson, Antimicrob. Agents Chemother. 2015, 59, 2785–2790
A. Asli, E. Brouillette, K. M. Krause, W. W. Nichols, F. Malouin, Antimicrob. Agents Chemother. 2016, 60, 752–756
N. A. C. Curtis, D. Orr, G. W. Ross, M. G. Boulton, Antimicrob. Agents Chemother. 1979, 16, 533–539
T. A. Davies, W. Shang, K. Bush, R. K. Flamm, Antimicrob. Agents Chemother. 2008, 52, 1510–1512
R. R. Chauvette, E. Flynn, J. Med. Chem. 1966, 9, 741–745
J. D. Cocker, S. Eardley, G. I. Gregory, M. E. Hall, A. G. Long, J. Chem. Soc. 1966, 1142–1151
D. B. Boyd, W. H. W. Lunn, J. Med. Chem. 1979, 22, 778–784
D. B. Boyd, J. Org. Chem. 1985, 50, 886–888
C. H. O'Callaghan, S. M. Kirby, A. Morris, R. E. Waller, R. E. Duncombe, J. Bacteriol. 1972, 110, 988–991
M. I. Page, Acc. Chem. Res. 1984, 17, 144–151
M. Galleni, J. M. Frère, Biochem. J. 1988, 255, 119–122
Similar publications
Sorry the service is unavailable at the moment. Please try again later.
This website uses cookies to improve user experience. Read more
Save & Close
Accept all
Decline all
Show detailsHide details
Cookie declaration
About cookies
Strictly necessary
Performance
Strictly necessary cookies allow core website functionality such as user login and account management. The website cannot be used properly without strictly necessary cookies.
This cookie is used by Cookie-Script.com service to remember visitor cookie consent preferences. It is necessary for Cookie-Script.com cookie banner to work properly.
Performance cookies are used to see how visitors use the website, eg. analytics cookies. Those cookies cannot be used to directly identify a certain visitor.
Used to store the attribution information, the referrer initially used to visit the website
Cookies are small text files that are placed on your computer by websites that you visit. Websites use cookies to help users navigate efficiently and perform certain functions. Cookies that are required for the website to operate properly are allowed to be set without your permission. All other cookies need to be approved before they can be set in the browser.
You can change your consent to cookie usage at any time on our Privacy Policy page.
