Rational Development of Bacterial Ureases Inhibitors.

Antimicrobials Computer-aided drug design Ebselen Enzyme Phosphonates

Journal

Chemical record (New York, N.Y.)
ISSN: 1528-0691
Titre abrégé: Chem Rec
Pays: United States
ID NLM: 101085550

Informations de publication

Date de publication:
Aug 2022
Historique:
revised: 28 03 2022
received: 08 02 2022
pubmed: 4 5 2022
medline: 10 8 2022
entrez: 3 5 2022
Statut: ppublish

Résumé

Urease, an enzyme that catalyzes the hydrolysis of urea, is a virulence factor of various pathogenic bacteria. In particular, Helicobacter pylori, that colonizes the digestive tract and Proteus spp., that can infect the urinary tract, are related to urease activity. Therefore, urease inhibitors are considered as potential therapeutics against these infections. This review describes current knowledge of the structures, activity, and biological importance of bacterial ureases. Moreover, the structure-based design of several classes of bacterial urease inhibitors is presented and discussed. Phosphinic and phosphonic acids were applied as transition-state analogues, while Michael acceptors and ebselen derivatives were applied as covalent binders of cysteine residue. This review incorporates bacterial urease inhibitors from literature published between 2008 and 2021.

Identifiants

pubmed: 35502852
doi: 10.1002/tcr.202200026
doi:

Substances chimiques

Enzyme Inhibitors 0
Urea 8W8T17847W
Urease EC 3.5.1.5

Types de publication

Journal Article Review

Langues

eng

Sous-ensembles de citation

IM

Pagination

e202200026

Subventions

Organisme : National Science Centre, Poland
ID : 2018/31/B/NZ6/02017

Informations de copyright

© 2022 The Chemical Society of Japan & Wiley-VCH GmbH.

Références

F. Wöhler, Annalen der Physik 1828, 88, 253-256.
R. P. Hausinger, Sci. Total Environ. 1994, 148, 157-66.
N. E. Dixon, T. C. Gazzola, R. L. blakeley, B. Zermer, J. Am. Chem. Soc. 1975, 97, 4131-3.
B. P. Callahan, Y. Yuan, R. Wolfenden, J. Am. Chem. Soc. 2005, 127, 10828-9.
R. K. Andrews, R. L. Blakeley, B. Zerner, Adv. Inorg. Biochem. 1984, 6, 245-83.
H. L. Mobley, R. P. Hausinger, Microbiol. Rev. 1989, 53, 85-108.
L. Alonso-Saez, A. S. Waller, D. R. Mende, K. Bakker, H. Farnelid, P. L. Yager, C. Lovejoy, J. E. Tremblay, M. Potvin, F. Heinrich, M. Estrada, L. Riemann, P. Bork, C. Pedros-Alio, S. Bertilsson, Proc. Natl. Acad. Sci. USA 2012, 109, 17989-94.
D. P. Hanlon, Comparative Biochemistry and Physiology Part B: Comparative Biochemistry 1975, 52, 261-264.
I. Konieczna, P. Zarnowiec, M. Kwinkowski, B. Kolesinska, J. Fraczyk, Z. Kaminski, W. Kaca, Curr. Protein Pept. Sci. 2012, 13, 789-806.
R. A. Burne, Y. Y. Chen, Microbes Infect. 2000, 2, 533-42.
M. P. Byrne, J. T. Tobin, P. J. Forrestal, M. Danaher, C. G. Nkwonta, K. Richards, E. Cummins, S. A. Hogan, T. F. O′Callaghan, Sustainability 2020, 12.
C. P. Witte, Plant Sci. 2011, 180, 431-438.
M. Garnica, F. Houdusse, A. M. Zamarreño, J. M. Garcia-Mina, J. Sci. Food Agric. 2010, 90, 357-369.
D. T. Britto, M. Y. Siddiqi, A. D. Glass, H. J. Kronzucker, Proc. Natl. Acad. Sci. USA 2001, 98, 4255-8.
S. San Francisco, O. Urrutia, V. Martin, A. Peristeropoulos, J. M. Garcia-Mina, J. Sci. Food Agric. 2011, 91, 1569-75.
X. Zhou, L. H. Wu, F. Dai, Yingyong Shengtai Xuebao 2016, 27, 4003-4012.
H. Cantarella, R. Otto, J. R. Soares, A. G. d. B. Silva, J. Adv. Res. 2018, 13, 19-27.
Z. Tian, J. J. Wang, S. Liu, Z. Zhang, S. K. Dodla, G. Myers, Sci. Total Environ. 2015, 533, 329-38.
S. Murchan, H. M. Aucken, L. O′Neill, G. M. Ganner, B. D. Cookson, J. Clin. Microbiol. 2004, 42, 5154-60.
C. E. Armbruster, H. L. T. Mobley, M. M. Pearson, EcoSal Plus 2018, 8.
S. Gatermann, J. John, R. Marre, Infect. Immun. 1989, 57, 110-6.
P. Bauerfeind, R. Garner, B. E. Dunn, H. L. Mobley, Gut 1997, 40, 25-30.
M. Tsujii, S. Kawano, S. Tsuji, H. Fusamoto, T. Kamada, N. Sato, Gastroenterology 1992, 102, 1881-8.
J. C. Rutherford, PLoS Pathog. 2014, 10, e1004062.
A. Martelli, P. Buli, V. Cortecchia, Eur. Urol. 1981, 7, 291-3.
A. Javor, D. Frang, Z. Nagy, Int. Urol. Nephrol. 1984, 16, 191-4.
M. Safavi, R. Sabourian, A. Foroumadi, World J. Clin. Cases 2016, 4, 5-19.
L. Mazzei, F. Musiani, S. Ciurli, in The Biological Chemistry of Nickel, The Royal Society of Chemistry, 2017, pp. 60-97.
R. Ligabue-Braun, F. C. Andreis, H. Verli, C. R. Carlini, Naturwissenschaften 2013, 100, 459-67.
B. Krajewska, J. Mol. Catal. B 2009, 59, 9-21.
K. Kappaun, A. R. Piovesan, C. R. Carlini, R. Ligabue-Braun, J. Adv. Res. 2018, 13, 3-17.
C. Hirayama, M. Sugimura, H. Saito, M. Nakamura, Phytochemistry 2000, 53, 325-30.
M. W. Lubbers, S. B. Rodriguez, N. K. Honey, R. J. Thornton, Can. J. Microbiol. 1996, 42, 132-40.
F. Mirbod, R. A. Schaller, G. T. Cole, Med. Mycol. 2002, 40, 35-44.
C. M. Collins, S. E. D′Orazio, Mol. Microbiol. 1993, 9, 907-13.
M. Jin, W. Rosario, E. Watler, D. H. Calhoun, Protein Expression Purif. 2004, 34, 111-7.
T. D. Schoep, A. Fulurija, F. Good, W. Lu, R. P. Himbeck, C. Schwan, S. S. Choi, D. E. Berg, P. R. Mittl, M. Benghezal, B. J. Marshall, PLoS One 2010, 5, e15042.
S. Benini, W. R. Rypniewski, K. S. Wilson, S. Ciurli, S. Mangani, JBIC J. Biol. Inorg. Chem. 1998, 3, 268-273.
L. Mazzei, F. Musiani, S. Ciurli, J. Biol. Inorg. Chem. 2020, 25, 829-845.
P. A. Karplus, M. A. Pearson, R. P. Hausinger, Acc. Chem. Res. 1997, 30, 330-337.
S. Benini, W. R. Rypniewski, K. S. Wilson, S. Miletti, S. Ciurli, S. Mangani, Structure 1999, 7, 205-16.
S. Benini, W. R. Rypniewski, K. S. Wilson, S. Miletti, S. Ciurli, S. Mangani, J. Biol. Inorg. Chem. 2000, 5, 110-8.
S. Benini, W. R. Rypniewski, K. S. Wilson, S. Ciurli, S. Mangani, J. Biol. Inorg. Chem. 2001, 6, 778-90.
S. Benini, W. R. Rypniewski, K. S. Wilson, S. Mangani, S. Ciurli, J. Am. Chem. Soc. 2004, 126, 3714-5.
F. Musiani, E. Arnofi, R. Casadio, S. Ciurli, JBIC J. Biol. Inorg. Chem. 2001, 6, 300-314.
M. A. Pearson, I.-S. Park, R. A. Schaller, L. O. Michel, P. A. Karplus, R. P. Hausinger, Biochemistry 2000, 39, 8575-8584.
M. J. Todd, R. P. Hausinger, Biochemistry 2000, 39(18), 5389-5396.
L. Mazzei, M. Cianci, U. Contaldo, S. Ciurli, J. Agric. Food Chem. 2019, 67(8), 2127-2138.
L. Mazzei, M. Cianci, S. Benini, S. Ciurli, Chemistry 2019, 25, 15351-15360.
L. Mazzei, M. Cianci, S. Benini, S. Ciurli, Angew. Chem. Int. Ed. 2019, 58(22), 7415-7419.
H. A. Krebs, Current Contents/Life Sciences 1980, 12-12.
J. J. Sigurdarson, S. Svane, H. Karring, Rev. Environ. Sci. Bio/Technol. 2018, 17, 241-258.
G. Estiu, K. M. Merz, JACS 2004, 126, 6932-6944.
S. Ciurli, S. Benini, W. R. Rypniewski, K. S. Wilson, S. Miletti, S. Mangani, Coord. Chem. Rev. 1999, 190-192, 331-355.
J. C. Polacco, M. A. Holland, in Int. Rev. Cytol., ed. by K. W. Jeon, J. Jarvik, Academic Press, 1993, Vol. 145, pp. 65-103.
L. V. Modolo, C. J. da-Silva, D. S. Brandão, I. S. Chaves, J. Adv. Res. 2018, 13, 29-37.
S. Kojima, A. Bohner, N. von Wiren, J. Membr. Biol. 2006, 212, 83-91.
H. Cantarella, R. Otto, J. R. Soares, A. G. B. Silva, J. Adv. Res. 2018, 13, 19-27.
J. M. Bremner, M. J. Krogmeier, Proc. Natl. Acad. Sci. USA 1988, 85, 4601-4.
P. Anbu, C. H. Kang, Y. J. Shin, J. S. So, Springerplus 2016, 5, 250.
D. Mora, S. Arioli, PLoS Pathog. 2014, 10, e1004472.
H. L. Mobley, M. D. Island, R. P. Hausinger, Microbiol. Rev. 1995, 59, 451-80.
L. M. Brown, Epidemiol. Rev. 2000, 22, 283-97.
H. L. T. Mobley, in Helicobacter pylori: Physiology and Genetics, ed. by H. L. T. Mobley, G. L. Mendz, S. L. Hazell, Washington (DC), 2001.
E. Morou-Bermudez, S. Rodriguez, A. S. Bello, M. G. Dominguez-Bello, PLoS One 2015, 10, e0139315.
E. Morou-Bermudez, R. A. Burne, Infect. Immun. 1999, 67, 504-12.
S. Svane, J. J. Sigurdarson, F. Finkenwirth, T. Eitinger, H. Karring, Sci. Rep. 2020, 10, 8503.
E. J. Beswick, I. V. Pinchuk, K. Minch, G. Suarez, J. C. Sierra, Y. Yamaoka, V. E. Reyes, Infect. Immun. 2006, 74, 1148-55.
J. Y. Zhang, T. Liu, H. Guo, X. F. Liu, Y. Zhuang, S. Yu, L. Chen, C. Wu, Z. Zhao, B. Tang, P. Luo, X. H. Mao, G. Guo, Y. Shi, Q. M. Zou, Immunobiology 2011, 216, 803-10.
J. H. Lee, S. H. Jun, J. M. Kim, S. C. Baik, J. C. Lee, J. Microbiol. 2015, 53, 406-14.
C. R. Carlini, R. Ligabue-Braun, Toxicon 2016, 110, 90-109.
R. K. Andrews, A. Dexter, R. L. Blakeley, B. Zerner, JACS 1986, 108, 7124-7125.
W. S. Faraci, B. V. Yang, D. O′Rourke, R. W. Spencer, Bioorg. Med. Chem. 1995, 3, 605-610.
S. Vassiliou, A. Grabowiecka, P. Kosikowska, A. Yiotakis, P. Kafarski, Ł. Berlicki, J. Med. Chem. 2008, 51, 5736-44.
A. Mucha, P. Kafarski, Ł. Berlicki, J. Med. Chem. 2011, 54, 5955-80.
Ł. Berlicki, M. Bochno, A. Grabowiecka, A. Bialas, P. Kosikowska, P. Kafarski, Amino Acids 2012, 42, 1937-45.
S. Vassiliou, P. Kosikowska, A. Grabowiecka, A. Yiotakis, P. Kafarski, Ł. Berlicki, J. Med. Chem. 2010, 53, 5597-606.
S. Vassiliou, A. Grabowiecka, P. Kosikowska, Ł. Berlicki, Arkivoc 2011, 2012, 33-43.
K. Macegoniuk, A. Dzielak, A. Mucha, Ł. Berlicki, ACS Med. Chem. Lett. 2015, 6, 146-50.
V. Ntatsopoulos, K. Macegoniuk, A. Mucha, S. Vassiliou, Ł. Berlicki, Eur. J. Med. Chem. 2018, 159, 307-316.
V. Ntatsopoulos, S. Vassiliou, K. Macegoniuk, Ł. Berlicki, A. Mucha, Eur. J. Med. Chem. 2017, 133, 107-120.
L. Mazzei, M. Cianci, F. Musiani, S. Ciurli, Dalton Trans. 2016, 45, 5455-9.
L. Mazzei, M. Cianci, F. Musiani, G. Lente, M. Palombo, S. Ciurli, J. Inorg. Biochem. 2017, 166, 182-189.
A. Pagoni, T. Daliani, K. Macegoniuk, S. Vassiliou, Ł. Berlicki, Bioorg. Med. Chem. Lett. 2019, 29, 1085-1089.
A. Pagoni, A. Grabowiecka, W. Tabor, A. Mucha, S. Vassiliou, Ł. Berlicki, J. Med. Chem. 2021, 64, 404-416.
K. Macegoniuk, E. Grela, J. Palus, E. Rudzinska-Szostak, A. Grabowiecka, M. Biernat, Ł. Berlicki, J. Med. Chem. 2016, 59, 8125-33.
F. C. Meotti, V. C. Borges, G. Zeni, J. B. T. Rocha, C. W. Nogueira, Toxicol. Lett. 2003, 143, 9-16.
K. Macegoniuk, E. Grela, M. Biernat, M. Psurski, G. Gościniak, A. Dziełak, A. Mucha, J. Wietrzyk, Ł. Berlicki, A. Grabowiecka, PLoS One 2017, 1, e182437.
E. Grela, A. Dziełak, K. Szydowska, A. Mucha, P. Kafarski, A. M. Grabowiecka, J. Med. Microbiol. 2016, 65, 1123-1129.

Auteurs

Saurabh Loharch (S)

Department of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University of Science and Technology, Wybrzeże Wyspiańskiego 27, 50-370, Wrocław, Poland.

Łukasz Berlicki (Ł)

Department of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University of Science and Technology, Wybrzeże Wyspiańskiego 27, 50-370, Wrocław, Poland.

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