In vitro advanced antimycobacterial screening of cobalt(II) and copper(II) complexes of fluorinated isonicotinoylhydrazones

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 23, 2004, Pages 5731-5733

  Maccari, Rosanna ^a   Ottanà, Rosaria ^a   Bottari, Bruno ^a,b   Rotondo, Enrico ^b   Vigorita, Maria Gabriella ^a  

^a UNIVERSITY OF MESSINA   (Italy)

^b Ch Fis Fac Sci MMFFNN Univ M

Author keywords

Antimycobacterial activity; Isoniazid derivatives; Metalcomplexes

Indexed keywords

ANTIMYCOBACTERIAL AGENT; CIPROFLOXACIN; COBALT COMPLEX; COPPER COMPLEX; ETHAMBUTOL; ISONIAZID; ISONICOTINOYLHYDRAZONE DERIVATIVE; KANAMYCIN; METAL COMPLEX; RIFAMPICIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL MODEL; ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL GROWTH; BACTERIAL STRAIN; BACTERICIDAL ACTIVITY; CERCOPITHECIDAE; CONCENTRATION (PARAMETERS); CONCENTRATION RESPONSE; CONTROLLED STUDY; CULTURE MEDIUM; DRUG SCREENING; FLUORINATION; MACROPHAGE; MYCOBACTERIUM INTRACELLULARE AVIUM; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; TUBERCULOSIS;

ANIMALS; ANTI-BACTERIAL AGENTS; COBALT; COPPER; DRUG EVALUATION, PRECLINICAL; FLUORINE; HYDRAZONES; ISONIAZID; MICE; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM TUBERCULOSIS;

MYCOBACTERIUM; MYCOBACTERIUM AVIUM; MYCOBACTERIUM AVIUM COMPLEX; MYCOBACTERIUM TUBERCULOSIS;

EID: 7044239372     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.09.052     Document Type: Article

References (25)

1. F.M. Collins Clin. Microb. Rev. 2 1989 360
2. N.M.H. Graham, N. Galai, K.E. Nelson, J. Astemborski, M. Bonds, R.T. Rizzo, L. Sheeley, and D. Vlahov Arch. Int. Med. 156 1996 889
3. N.A. Halsey, J.S. Coberly, J. Desormeaux, P. Losikoff, J. Atkinson, L.H. Moulton, M. Contave, M. Johnson, H. Davis, L. Geiter, E. Johnson, R. Huebner, R. Boulos, and R.E. Chaisson Lancet 351 1998 786
4. C.B. Inderlied, C.A. Kemper, and L.E.M. Bermudez Clin. Microb. Rev. 6 1993 266
5. L.A. Basso, and J.S. Blanchard Adv. Exp. Med. Biol. 456 1998 115
6. I. Bastian, and R. Colebunders Drugs 58 1999 633
7. G.L. Mandell, and W.A. Petri Jr. Goodman and Gilman’s The Pharmacological Basis of Therapeutics 1996 McGraw-Hill 1155 1174
8. P. Sensi, and G. Gialdroni Grassi M.E. Wolff Burger’s Medicinal Chemistry and Drug Discovery 1996 John Wiley and Sons New York 575 635
9. TAACF Web Site: www.taacf.org
10. E.E. Telzak, K. Sepkowitz, P. Alpert, S. Mannheimer, F. Medard, W. El-Sadr, S. Blum, A. Gagliardi, N. Salomon, and G. Turett New Engl. J. Med. 333 1995 907
11. WHO Web Site: www.who.int/en/
12. B. Bottari, R. Maccari, F. Monforte, R. Ottanà, E. Rotondo, and M.G. Vigorita Bioorg. Med. Chem. Lett. 10 2000 657
13. B. Bottari, R. Maccari, F. Monforte, R. Ottanà, E. Rotondo, and M.G. Vigorita Bioorg. Med. Chem. Lett. 11 2001 301
14. B. Bottari, R. Maccari, F. Monforte, R. Ottanà, M.G. Vigorita, G. Bruno, F. Nicolò, A. Rotondo, and E. Rotondo Bioorg. Med. Chem. 9 2001 2203
15. R. Maccari, R. Ottanà, F. Monforte, and M.G. Vigorita Antimicrob. Agents Chemother. 46 2002 294
16. M.G. Vigorita, M. Basile, C. Zappalà, G. Gabbrielli, and F. Pizzimenti Il Farmaco 47 1992 893
17. M.G. Vigorita, R. Ottanà, C. Zappalà, R. Maccari, F.C. Pizzimenti, and G. Gabbrielli Il Farmaco 49 1994 775
18. M.G. Vigorita, R. Ottanà, C. Zappalà, R. Maccari, F.C. Pizzimenti, and G. Gabbrielli Il Farmaco 50 1995 783
19. Cobalt(II) and copper(II) complexes 1, 2 were synthesized by the reaction of the corresponding ISNE with cobalt(II) nitrate or copper(II) acetate, respectively, in molar ratio 2:1, at 50°C in methanol. Concentrated solutions, left at room temperature for 24 h, provided powders, which were further purified by repeated washing with hot methanol. The formation of neutral 1:2 complexes was monitored by means of the electronic spectra of the reagents. Experimental data (IR spectra, magnetic moments, pH measurements) indicated the formation of enolates and supported the proposed octahedral coordination geometry. The stability of the metalcomplexes in conditions mimicking those employed for antimycobacterial assays (phosphate buffer: pH 6.5/6.8; 37°C; 10 days) was verified and no breakdown was evidenced
20. P.S. Skinner, S.K. Furney, M.R. Jacobs, G. Klopman, J.J. Ellner, and I.M. Orme Antimicrob. Agents Chemother. 38 1994 2557
21. N.A. Carlone, A.M. Cuffini, V. Tullio, and G. Cavallo J. Chemother. 3 1991 98
22. W.L. Hand, and N.L. King-Thompson Antimicrob. Agents Chemother. 34 1990 1189
23. L.A. Collins, and S.G. Franzblau Antimicrob. Agents Chemother. 41 1997 1004
24. S.G. Franzblau, R.S. Witzig, J.C. McLaughlin, P. Torres, G. Madico, A. Hernandez, M.T. Degnan, M.B. Cook, V.K. Quenzer, R.M. Freguson, and R.H. Gilman J. Clin. Microb. 36 1998 362
25. The minimum bactericidal concentration (MBC) was determined for M. tuberculosis H37Rv and for the appropriate drug-resistant strain by subculturing onto drug-free solid media and enumerating CFU after exposure in supplemented Middlebrook 7H9 media to drug concentrations equivalent to and higher than the previously determined MICs against the respective strains