Promising Antifungal and Antibacterial Agents Based on 5-Aryl-2,2'-bipyridines and Their Heteroligand Salicylate Metal Complexes: Synthesis, Bioevaluation, Molecular Docking.
Animals
Anti-Bacterial Agents
/ chemical synthesis
Antifungal Agents
/ chemical synthesis
Cell Survival
/ drug effects
Coordination Complexes
/ chemical synthesis
Dose-Response Relationship, Drug
Fungi
/ drug effects
HEK293 Cells
Humans
Metals, Heavy
/ chemistry
Mice
Microbial Sensitivity Tests
Molecular Docking Simulation
Molecular Structure
Neisseria gonorrhoeae
/ drug effects
Salicylates
/ chemistry
Structure-Activity Relationship
5-aryl-2,2′-bipyridines
S. aureus DNA gyrases
antimicrobial activity
metal heteroligand complexes
molecular docking
salicylates
Journal
ChemMedChem
ISSN: 1860-7187
Titre abrégé: ChemMedChem
Pays: Germany
ID NLM: 101259013
Informations de publication
Date de publication:
04 02 2022
04 02 2022
Historique:
revised:
11
11
2021
received:
31
08
2021
pubmed:
17
11
2021
medline:
19
2
2022
entrez:
16
11
2021
Statut:
ppublish
Résumé
A series of new 5-aryl-2,2'-bipyridines and their (polyfluoro)salicylate complexes of Cu(II), Co(II) and Mn(II) were synthesized. Their antimicrobial activity was evaluated in vitro against six strains of Trichophytons, E. floccosum, M. canis, C. ablicans and Gram-negative bacteria N. gonorrhoeae. Among azo-ligands, Ph-bipy and Tol-bipy showed promising antifungal activity (minimum inhibitory concentration (MIC)<0.8-27 μM). Their antifungal action was found can be realized via binding Fe(III) ions. Tol-bipy suppressed growth of Gram-positive bacteria S. aureus, S. aureus MRSA and their monospecies biofilms (MIC 6-16 μM). Using molecular docking, the anti-staphylococcal action mechanism based on the inhibition of S. aureus DNA gyrase GyrB was proposed for the lead compounds. Among metal complexes, Cu(II) and Mn(II) complexes based on tetrafluorosalicylic acid and Tol-bipy or Ph-bipy had the high antifungal activity (MIC<0.24-32 μM). Mn(SalF
Identifiants
pubmed: 34783161
doi: 10.1002/cmdc.202100577
doi:
Substances chimiques
Anti-Bacterial Agents
0
Antifungal Agents
0
Coordination Complexes
0
Metals, Heavy
0
Salicylates
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202100577Subventions
Organisme : Ministry of Science and Higher Education of the Russian Federation
ID : 075-15-2020-777
Organisme : Center for Joint Use "Spectroscopy and Analysis of Organic Compounds" at the Postovsky Institute of Organic Synthesis of UB RAS
Organisme : Perm National Research Polytechnic University, Russia
Informations de copyright
© 2021 Wiley-VCH GmbH.
Références
C. Ghosh, P. Sarkar, R. Issa, J. Haldar, Trends Microbiol. 2019, 27, 323-338.
H. W. Boucher, G. H. Talbot, J. S. Bradley, J. E. Edwards, D. Gilbert, L. B. Rice, M. Scheld, B. Spellberg, J. Bartlett, Clin. Infect. Dis. 2009, 48, 1-12.
N. M. Revie, K. R. Iyer, N. Robbins, L. E. Cowen, Curr. Opin. Microbiol. 2018, 45, 70-76.
F. Almeida, M. L. Rodrigues, C. Coelho, Front. Microbiol. 2019, 10, 214.
M. W. McCarthy, T. J. Walsh, Expert Rev. Anti-Infect. Ther. 2017, 15, 577-584.
N. Wiederhold, Infect. Drug Resist. 2017, 10, 249-259.
E. M. Carmona, A. H. Limper, Clin. Chest Med. 2017, 38, 393-402.
K. V. S. Mani Chandrika, S. Sharma, Bioorg. Med. Chem. 2020, 28, 115398.
J. R. Köhler, B. Hube, R. Puccia, A. Casadevall, J. R. Perfect, Microbiol. Spectr. 2017, 5, DOI 10.1128/microbiolspec.FUNK-0014-2016.
W. Liu, L. Yuan, S. Wang, J. Med. Chem. 2020, 63, 12429-12459.
D. A. Enoch, H. Yang, S. H. Aliyu, C. Micallef, Hum. Fungal Pathog. Identification. Methods Mol. Biol. (Ed.: T. Lion) 2017, pp. 17-65.
H. F. Chambers, F. R. DeLeo, Nat. Rev. Microbiol. 2009, 7, 629-641.
E. Tacconelli, E. Carrara, A. Savoldi, S. Harbarth, M. Mendelson, D. L. Monnet, C. Pulcini, G. Kahlmeter, J. Kluytmans, Y. Carmeli, M. Ouellette, K. Outterson, J. Patel, M. Cavaleri, E. M. Cox, C. R. Houchens, M. L. Grayson, P. Hansen, N. Singh, U. Theuretzbacher, N. Magrini, A. O. Aboderin, S. S. Al-Abri, N. Awang Jalil, N. Benzonana, S. Bhattacharya, A. J. Brink, F. R. Burkert, O. Cars, G. Cornaglia, O. J. Dyar, A. W. Friedrich, A. C. Gales, S. Gandra, C. G. Giske, D. A. Goff, H. Goossens, T. Gottlieb, M. Guzman Blanco, W. Hryniewicz, D. Kattula, T. Jinks, S. S. Kanj, L. Kerr, M.-P. Kieny, Y. S. Kim, R. S. Kozlov, J. Labarca, R. Laxminarayan, K. Leder, L. Leibovici, G. Levy-Hara, J. Littman, S. Malhotra-Kumar, V. Manchanda, L. Moja, B. Ndoye, A. Pan, D. L. Paterson, M. Paul, H. Qiu, P. Ramon-Pardo, J. Rodríguez-Baño, M. Sanguinetti, S. Sengupta, M. Sharland, M. Si-Mehand, L. L. Silver, W. Song, M. Steinbakk, J. Thomsen, G. E. Thwaites, J. W. van der Meer, N. Van Kinh, S. Vega, M. V. Villegas, A. Wechsler-Fördös, H. F. L. Wertheim, E. Wesangula, N. Woodford, F. O. Yilmaz, A. Zorzet, Lancet Infect. Dis. 2018, 18, 318-327.
L.-L. Zhou, C.-G. Yang, Chin. J. Chem. 2019, 37, 183-193.
M. Unemo, C. del Rio, W. M. Shafer, Microbiol. Spectr. 2016, 4, 213-238.
M. W. McCarthy, D. P. Kontoyiannis, O. A. Cornely, J. R. Perfect, T. J. Walsh, J. Infect. Dis. 2017, 216, S474-S483.
K. L. Haas, K. J. Franz, Chem. Rev. 2009, 109, 4921-4960.
M. Pervaiz, S. Sadiq, A. Sadiq, U. Younas, A. Ashraf, Z. Saeed, M. Zuber, A. Adnan, Coord. Chem. Rev. 2021, 447, 214128.
I. Cota, V. Marturano, B. Tylkowski, Coord. Chem. Rev. 2019, 396, 49-71.
S. Medici, M. Peana, V. M. Nurchi, J. I. Lachowicz, G. Crisponi, M. A. Zoroddu, Coord. Chem. Rev. 2015, 284, 329-350.
S. Nasiri Sovari, F. Zobi, Chemistry 2020, 2, 418-452.
A. Frei, Antibiotics 2020, 9, 90.
M. A. Sierra, L. Casarrubios, M. C. de la Torre, Chem. A Eur. J. 2019, 25, 7232-7242.
L. J. Boerner, J. M. Zaleski, Curr. Opin. Chem. Biol. 2005, 9, 135-144.
H.-K. Liu, P. J. Sadler, Acc. Chem. Res. 2011, 44, 349-359.
S. Tabassum, M. Zaki, F. Arjmand, I. Ahmad, J. Photochem. Photobiol. B 2012, 114, 108-118.
G. Crisponi, V. M. Nurchi, D. Fanni, C. Gerosa, S. Nemolato, G. Faa, Coord. Chem. Rev. 2010, 254, 876-889.
A. Grubman, A. R. White, Expert Rev. Mol. Med. 2014, 16, e11.
P. V. Bernhardt, G. A. Lawrance, Compr. Coord. Chem. II, Elsevier 2003, pp. 1-145.
P. J. Sadler, Adv. Inorg. Chem. (Ed.: A. G. Sykes) 1991, pp. 1-48.
T. Jun, W. Bochu, Z. Liancai, Bioorg. Med. Chem. Lett. 2007, 17, 1197-1199.
P. Nordell, P. Lincoln, J. Am. Chem. Soc. 2005, 127, 9670-9671.
G.-J. Chen, X. Qiao, P.-Q. Qiao, G.-J. Xu, J.-Y. Xu, J.-L. Tian, W. Gu, X. Liu, S.-P. Yan, J. Inorg. Biochem. 2011, 105, 119-126.
T. Afrati, A. A. Pantazaki, C. Dendrinou-Samara, C. Raptopoulou, A. Terzis, D. P. Kessissoglou, Dalton Trans. 2010, 39, 765-775.
Q. Wang, W. Li, F. Gao, S. Li, J. Ni, Z. Zheng, Polyhedron 2010, 29, 539-543.
C. Kaes, A. Katz, M. W. Hosseini, Chem. Rev. 2000, 100, 3553-3590.
F. Dwyer, I. Reid, A. Shulman, G. M. Laycock, S. Dixson, Aust. J. Exp. Biol. Med. Sci. 1969, 47, 203-218.
T. Y. Hargrove, Z. Wawrzak, P. W. Alexander, J. H. Chaplin, M. Keenan, S. A. Charman, C. J. Perez, M. R. Waterman, E. Chatelain, G. I. Lepesheva, J. Biol. Chem. 2013, 288, 31602-31615.
L. Galeazzi, P. Bocci, A. Amici, L. Brunetti, S. Ruggieri, M. Romine, S. Reed, A. L. Osterman, D. A. Rodionov, L. Sorci, N. Raffaelli, J. Biol. Chem. 2011, 286, 40365-40375.
D. Chen, Q. Zhao, W. Liu, J. Ind. Microbiol. Biotechnol. 2019, 46, 459-468.
S. Jahani, M. Khorasani-Motlagh, M. Noroozifar, J. Biomol. Struct. Dyn. 2016, 34, 612-624.
Z. Aramesh-Boroujeni, M. Khorasani-Motlagh, M. Noroozifar, J. Biomol. Struct. Dyn. 2016, 34, 414-426.
Z. Aramesh-Boroujeni, N. Aramesh, S. Jahani, M. Khorasani-Motlagh, K. Kerman, M. Noroozifar, J. Biomol. Struct. Dyn. 2020, 39, 5105-5116.
Z. Aramesh-Boroujeni, S. Jahani, M. Khorasani-Motlagh, K. Kerman, M. Noroozifar, J. Biomol. Struct. Dyn. 2019, 38, 1711-1725.
Z. Aramesh-Boroujeni, S. Jahani, M. Khorasani-Motlagh, K. Kerman, N. Aramesh, S. Asadpour, M. Noroozifar, J. Biomol. Struct. Dyn. 2020, 38, 4746-4763.
M. Geraghty, V. Sheridan, M. McCann, M. Devereux, V. McKee, Polyhedron 1999, 18, 2931-2939.
O. O. E. Onawumi, O. A. Odunola, E. Suresh, P. Paul, Inorg. Chem. Commun. 2011, 14, 1626-1631.
R. Senthil Kumar, K. Sasikala, S. Arunachalam, J. Inorg. Biochem. 2008, 102, 234-241.
S. Bu, G. Jiang, G. Jiang, J. Liu, X. Lin, J. Shen, Y. Xiong, X. Duan, J. Wang, X. Liao, JBIC J. Biol. Inorg. Chem. 2020, 25, 747-757.
F. Gomes da Silva Dantas, A. Araújo de Almeida-Apolonio, R. Pires de Araújo, L. Regiane Vizolli Favarin, P. Fukuda de Castilho, F. de Oliveira Galvão, T. Inez Estivalet Svidzinski, G. Antônio Casagrande, K. Mari Pires de Oliveira, Molecules 2018, 23, 1856.
G. Vasile Scăeţeanu, M. Chifiriuc, C. Bleotu, C. Kamerzan, L. Măruţescu, C. Daniliuc, C. Maxim, L. Calu, R. Olar, M. Badea, Molecules 2018, 23, 157.
T. S. Lobana, S. Indoria, A. K. Jassal, H. Kaur, D. S. Arora, J. P. Jasinski, Eur. J. Med. Chem. 2014, 76, 145-154.
S. Alimirzaei, M. Behzad, S. Abolmaali, Z. Abbasi, J. Mol. Struct. 2020, 1200, 127148.
Z. Wang, J. Li, B. M. Benin, B. Yu, S. D. Bunge, N. Abeydeera, S. D. Huang, M.-H. Kim, J. Med. Chem. 2021, 64, 9381-9388.
M. N. Patel, B. S. Bhatt, P. A. Dosi, Appl. Biochem. Biotechnol. 2012, 166, 1949-1968.
M. Geraghty, V. Sheridan, M. McCann, M. Devereux, V. McKee, Polyhedron 1999, 18, 2931-2939.
I. V. Shchur, E. V. Shchegolkov, Y. V. Burgart, A. N. Kozitsina, A. V. Ivanova, I. S. Alyamovskaya, N. P. Evstigneeva, N. A. Gerasimova, I. N. Ganebnykh, N. V. Zilberberg, N. V. Kungurov, V. I. Saloutin, O. N. Chupakhin, Polyhedron 2020, 177, 114279.
E. V. Shchegolkov, I. V. Shchur, Y. V. Burgart, P. A. Slepukhin, N. P. Evstigneeva, N. A. Gerasimova, N. V. Zilberberg, N. V. Kungurov, V. I. Saloutin, O. N. Chupakhin, Polyhedron 2021, 194, 114900.
I. V. Shchur, Y. V. Burgart, E. V. Shchegolkov, N. A. Gerasimova, N. P. Evstigneeva, N. V. Zilberberg, N. V. Kungurov, V. I. Saloutin, O. N. Chupakhin 2019, RU2706702.
E. V. Shchegol'kov, I. V. Shchur, Y. V. Burgart, V. I. Saloutin, S. Y. Solodnikov, O. P. Krasnykh, M. A. Kravchenko, Bioorg. Med. Chem. Lett. 2016, 26, 2455-2458.
E. V. Shchegol'kov, I. V. Shchur, Y. V. Burgart, V. I. Saloutin, A. N. Trefilova, G. A. Ljushina, S. Y. Solodnikov, L. N. Markova, V. V. Maslova, O. P. Krasnykh, S. S. Borisevich, S. L. Khursan, Bioorg. Med. Chem. 2017, 25, 91-99.
I. V. Shchur, E. V. Shchegolkov, Y. V. Burgart, G. A. Triandafilova, V. V. Maslova, S. Y. Solodnikov, O. P. Krasnykh, S. S. Borisevich, S. L. Khursan, V. I. Saloutin, ChemistrySelect 2019, 4, 1483-1490.
Y. V. Burgart, I. V. Shchur, E. V. Shchegolkov, V. I. Saloutin, Mendeleev Commun. 2020, 30, 636-638.
D. Ekinci, M. Şentürk, Ö. İ Küfrevioğlu, Expert Opin. Ther. Pat. 2011, 21, 1831-1841.
W. R. Dolbier, J. Fluorine Chem. 2005, 126, 157-163.
T. Suksrichavalit, S. Prachayasittikul, C. Nantasenamat, C. Isarankura-Na-Ayudhya, V. Prachayasittikul, Eur. J. Med. Chem. 2009, 44, 3259-3265.
F. Arjmand, B. Mohani, S. Ahmad, Eur. J. Med. Chem. 2005, 40, 1103-1110.
A. Toscani, C. Hind, M. Clifford, S.-H. Kim, A. Gucic, C. Woolley, N. Saeed, K. M. Rahman, J. M. Sutton, D. Castagnolo, Eur. J. Med. Chem. 2021, 213, 113172.
G. Kumar, S. Devi, R. Johari, D. Kumar, Eur. J. Med. Chem. 2012, 52, 269-274.
F. Briganti, A. Scozzafava, C. Supuran, Eur. J. Med. Chem. 1997, 32, 901-910.
B. B. Dey, J. Chem. Soc. Trans. 1914, 105, 1039-1046.
V. N. Kozhevnikov, O. V. Shabunina, D. S. Kopchuk, M. M. Ustinova, B. König, D. N. Kozhevnikov, Tetrahedron 2008, 64, 8963-8973.
P. Lemoine, B. Viossat, G. Morgant, F. T. Greenaway, A. Tomas, N.-H. Dung, J. R. Sorenson, J. Inorg. Biochem. 2002, 89, 18-28.
J. D. MacLowry, M. J. Jaqua, S. T. Selepak, Appl. Microbiol. 1970, 20, 46-53.
J. W. Rippon, Medical Mycology: The Pathogenic Fungi and the Pathogenic Actinomycetes. 3rd Ed., Saunders, Philadelphia, PA1988.
H. Price, D. R. Taylor, Calif. Med. 1952, 76, 283-288.
S. Shafiee, A. R. Khosravi, I. Ashrafi Tamai, Mycoses 2014, 57, 507-512.
G. S. de Hoog, K. Dukik, M. Monod, A. Packeu, D. Stubbe, M. Hendrickx, C. Kupsch, J. B. Stielow, J. Freeke, M. Göker, A. Rezaei-Matehkolaei, H. Mirhendi, Y. Gräser, Mycopathologia 2017, 182, 5-31.
S. Silva, M. Negri, M. Henriques, R. Oliveira, D. W. Williams, J. Azeredo, FEMS Microbiol. Rev. 2012, 36, 288-305.
P. Mastromarino, B. Vitali, L. Mosca, New Microbiol. 2013, 36, 229-238.
N. S. Naik, L. A. Shastri, S. D. Joshi, S. R. Dixit, B. M. Chougala, S. Samundeeswari, M. Holiyachi, F. Shaikh, J. Madar, R. Kulkarni, V. Sunagar, Bioorg. Med. Chem. 2017, 25, 1413-1422.
T. Ponnusamy, M. Alagumuthu, S. Thamaraiselvi, Bioorg. Med. Chem. 2018, 26, 3438-3452.
S. N. Dighe, T. A. Collet, Eur. J. Med. Chem. 2020, 199, 112326.
B. D. Bax, P. F. Chan, D. S. Eggleston, A. Fosberry, D. R. Gentry, F. Gorrec, I. Giordano, M. M. Hann, A. Hennessy, M. Hibbs, J. Huang, E. Jones, J. Jones, K. K. Brown, C. J. Lewis, E. W. May, M. R. Saunders, O. Singh, C. E. Spitzfaden, C. Shen, A. Shillings, A. J. Theobald, A. Wohlkonig, N. D. Pearson, M. N. Gwynn, Nature 2010, 466, 935-940.
D. Sutormin, N. Rubanova, M. Logacheva, D. Ghilarov, K. Severinov, Nucleic Acids Res. 2019, 47, 1373-1388.
S. M. Ronkin, M. Badia, S. Bellon, A.-L. Grillot, C. H. Gross, T. H. Grossman, N. Mani, J. D. Parsons, D. Stamos, M. Trudeau, Y. Wei, P. S. Charifson, Bioorg. Med. Chem. Lett. 2010, 20, 2828-2831.
M. Niewerth, D. Kunze, M. Seibold, M. Schaller, H. C. Korting, B. Hube, Antimicrob. Agents Chemother. 2003, 47, 1805-1817.
W. Raza, W. Hongsheng, S. Qirong, Brazilian Arch. Biol. Technol. 2010, 53, 1145-1154.
H.-S. Ko, H. Tindwa, R. De Jin, Y.-S. Lee, S.-H. Hong, H.-N. Hyun, Y. Nam, K.-Y. Kim, Korean J. Soil Sci. Fertil. 2011, 44, 650-656.
A. Mohindru, J. M. Fisher, M. Rabinovitz, Biochem. Pharmacol. 1983, 32, 3627-3632.
E. W. Ainscough, A. M. Brodie, W. A. Denny, G. J. Finlay, J. D. Ranford, J. Inorg. Biochem. 1998, 70, 175-185.
A. Geersing, N. Ségaud, M. G. P. van der Wijst, M. G. Rots, G. Roelfes, Inorg. Chem. 2018, 57, 7748-7756.
C. C. Ayala-Aguilera, T. Valero, Á. Lorente-Macías, D. J. Baillache, S. Croke, A. Unciti-Broceta, J. Med. Chem. 2021, article ASAP, acs.jmedchem.1c00963.
D. K. Chand, H.-J. Schneider, A. Bencini, A. Bianchi, C. Giorgi, S. Ciattini, B. Valtancoli, Chem. A Eur. J. 2000, 6, 4001-4008.
P. R. Reddy, A. Shilpa, Polyhedron 2011, 30, 565-572.
A. Jayamani, N. Sengottuvelan, G. Chakkaravarthi, Polyhedron 2014, 81, 764-776.
M.-J. Li, T.-Y. Lan, Z.-S. Lin, C. Yi, G.-N. Chen, JBIC J. Biol. Inorg. Chem. 2013, 18, 993-1003.
F. B. Tamboura, M. Gaye, A. S. Sall, A. H. Barry, T. Jouini, Inorg. Chem. Commun. 2002, 5, 235-238.
S. Dhar, A. R. Chakravarty, Inorg. Chem. 2003, 42, 2483-2485.
S. Dhar, P. A. N. Reddy, M. Nethaji, S. Mahadevan, M. K. Saha, A. R. Chakravarty, Inorg. Chem. 2002, 41, 3469-3476.
M. Jeżowska-Bojczuk, K. Stokowa-Sołtys, Eur. J. Med. Chem. 2018, 143, 997-1009.