Antibacterial, antifungal and antileishmanial activities of indolone-N-oxide derivatives

Journal of Antibiotics

Volumn 65, Issue 10, 2012, Pages 499-504

  Ibrahim, Hany ^a,b   Furiga, Aurelie ^c   Najahi, Ennaji ^d   Pigasse Hénocq, Christel ^c   Nallet, Jean Pierre ^e   Roques, Christine ^c   Aubouy, Agnes ^a,b   Sauvain, Michel ^a,b,f   Constant, Patricia ^g   Daffé, Mamadou ^g   Nepveu, Françoise ^a,b  

^a UNIVERSITÉ DE TOULOUSE   (France)

^b Hôpital Purpan   (France)

^c CNRS   (France)

^d UNIVERSITY OF SFAX   (Tunisia)

^e IDEALP PHARMA   (France)

^f UNIVERSIDAD PERUANA CAYETANO HEREDIA   (Peru)

^g UNIVERSITÉ PAUL SABATIER   (France)

Author keywords

antibacterial; antifungal; antileishmanial; antitubercular; broad spectrum; indolone N oxide; redox pharmacophore

Indexed keywords

2 PHENYLINDOLONE N OXIDE; ANTIBIOTIC AGENT; ANTIFUNGAL AGENT; BIFONAZOLE; CIPROFLOXACIN; CLOTRIMAZOLE; INDOLE DERIVATIVE; INDOLONE N OXIDE DERIVATIVE; NALIDIXIC ACID; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIBACTERIAL ACTIVITY; ANTIBIOTIC SENSITIVITY; ANTIFUNGAL ACTIVITY; ANTIPROTOZOAL ACTIVITY; ARTICLE; ASPERGILLUS NIGER; BACTERIAL GROWTH; BACTERIAL STRAIN; BACTERIUM CULTURE; CANDIDA ALBICANS; CELL ADHESION; CONTROLLED STUDY; CYTOTOXICITY; DRUG POTENCY; DRUG SOLUBILITY; ENTEROCOCCUS HIRAE; ESCHERICHIA COLI; FUNGAL STRAIN; FUNGUS CULTURE; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; LEISHMANIA; LEISHMANIA INFANTUM; LIPOPHILICITY; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PHARMACODYNAMICS; PRIORITY JOURNAL; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; ANTIPROTOZOAL AGENTS; INDOLES; MICROBIAL VIABILITY; OXIDES; STRUCTURE-ACTIVITY RELATIONSHIP;

ASPERGILLUS NIGER; BACTERIA (MICROORGANISMS); CANDIDA ALBICANS; ENTEROCOCCUS HIRAE; ESCHERICHIA COLI; LEISHMANIA AMAZONENSIS; LEISHMANIA INFANTUM; MYCOBACTERIUM TUBERCULOSIS; NEGIBACTERIA; POSIBACTERIA; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS;

EID: 84868125592     PISSN: 00218820     EISSN: 18811469     Source Type: Journal    
DOI: 10.1038/ja.2012.60     Document Type: Article

References (23)

1. Motiwala, A. S. et al. Mutations in extensively drug resistant Mycobacterium tuberculosis that do not code for known drug-resistance mechanisms. J. Infect. Dis. 201, 881-888 (2010
2. Donadio, S., Maffioli, S., Monciardini, P., Sosio, M. & Jabes, D. Antibiotic discovery in the twenty-first century: Current trends and future perspectives. J. Antibiot. 63, 423-430 (2010
3. Thomson, C. J., Power, E., Ruebsamen-Waigmann, H. & Labischinski, H. Antibacterial research and development in the 21st Century - an industry perspective of the challenges. Curr. Opin. Microbiol. 7, 445-450 (2004
4. Donadio, S., Maffioli, S., Monciardini, P., Sosio, M. & Jabes, D. Sources of novel antibiotics - aside the common roads. Appl. Microbiol. Biotechnol. 88, 1261-1267 (2010
5. Nepveu, F. et al. Synthesis and antiplasmodial activity of new indolone N-oxide derivatives. J. Med. Chem. 53, 699-714 (2010
6. Tahar, R. et al. Indolone-N-oxide derivatives: In vitro activity against fresh clinical isolates of Plasmodium falciparum, stage specificity and in vitro interactions with established antimalarial drugs. J. Antimicrob. Chemother. 66, 2566-2572 (2011
7. Ibrahim, H. et al. Pharmacological properties of indolone-N-oxides controlled by a bioreductive transformation in red blood cells? Med. Chem. Comm. 2, 860-869 (2011
8. Pantaleo, A. et al. New anti-Antimarial indolone-N-oxides, generating stable radical species, promote destabilization of the host cell membrane at early stages of P. falciparum growth. Free Radical. Bio. Med. 52, 527-536 (2012
9. Ibrahim, N., Ibrahim, H., Kim, S., Nallet, J. P. & Nepveu, F. Interactions between antimalarial indolone-N-oxide derivatives and human serum albumin. Biomacromolecules11, 3341-3351 (2010
10. Boyer, J., Bernardes-Genisson, V., Farines, V., Souchard, J. P. & Nepveu, F. 2-substituted-3H-indol-3-one-1-oxides: Preparation and radical trapping properties. Free Rad. Res. 38, 459-471 (2004
11. Polovyanenko, D. N., Plyusnin, V. F., Reznikov, V. A., Khramtsov, V. V. & Bagryanskaya, E. G. Mechanistic studies of the reactions of nitrone spin trap PBN with glutathiyl radical. J. Phys. Chem. B 112, 4841-4847 (2008
12. Hansen, M. B., Nielsen, S. E. & Berg, K. Re-examination and further development of a precise and rapid dye method for measuring cell growth/cell kill. J. Immunol. Methods 119, 203-210 (1989
13. Gomez-Flores, R., Gupta, S., Tamez-Guerra, R. & Mehta, R. T. Determination of MICs for Mycobacterium avium-M. intracellular complex in liquid medium by a colorimetric method. J. Clin. Microbiol. 33, 1842-1846 (1995
14. Estevez, Y. et al. Evaluation of the leishmanicidal activity of plants used by Peruvian Chayahuita ethnic group. J. Ethnopharmacol. 114, 254-259 (2007
15. Sereno, D., Roy, G., Lemesre, J. L., Papadopoulou, B. & Ouellette, M. DNA transformation of Leishmania infantum axenic amastigotes and their use in drug screening. Antimicrob. Agents Chemother. 45, 1168-1173 (2001
16. Sereno, D. & Lemesre, J-L. Axenically cultured amastigote forms as an in vitro model for investigation of antileishmanial agents. Antimicrob. Agents Chemother. 41, 972-976 (1997
17. Sereno, D. & Lemesre, J. L. Use of an enzymatic micromethod to quantify amastigote stage of Leishmania amazonensis in vitro. Parasitol. Res. 83, 401-403 (1997
18. Sauvain, M. et al. In vitro and in vivo leishmanicidal activities of natural and synthethic quinoids. Phytother. Res. 7, 167-171 (1993
19. Emami, S., Falahati, M., Banifatemi, A. & Shafiee, A. Stereoselective synthesis and antifungal activity of (Z)-trans-3-Azolyl-2-methylchromanone oxime ethers. Bioorg. Med. Chem. 12, 5881-5889 (2004
20. Sharma, D. et al. Synthesis, antimicrobial and antiviral evaluation of substituted imidazole derivatives. Eur. J. Med. Chem. 44, 2347-2353 (2009
21. ALOGPS 21 http://www.virtuallaboratory.org/lab/alogps/access date 15-16 February 2012.
22. Kaye, P. & Scott, P. Leishmaniasis: Complexity at the host-pathogen interface. Nat. Rev. Microbiol. 9, 604-615 (2011
23. Braun, J. S., Novak, R., Gao, G., Murray, P. J. & Shenep, J. L. Pneumolysin, a protein toxin of Streptococcus pneumoniae, induces nitric oxide production from macrophages. Infect. Immun. 67, 3750-3756 (1999