Towards calixarene-based prodrugs: Drug release and antibacterial behaviour of a water-soluble nalidixic acid/calix[4]arene ester adduct

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 10, 2009, Pages 2679-2682

  Dibama, Hugues Massimba ^a   Clarot, Igor ^a   Fontanay, Stéphane ^a   Salem, Adel Ben ^b   Mourer, Maxime ^a   Finance, Chantal ^a   Duval, Raphaël E ^a   Regnouf de Vains, Jean Bernard ^a  

^a NANCY UNIVERSITÉ   (France)

^b University of Sfax   (Tunisia)

Author keywords

Calixarene; Nalidixic acid; Prodrug; Quinolone

Indexed keywords

CALIXARENE; NALIDIXIC ACID; PRODRUG; TETRA 4 (AMINOETHYL)CALIX[4]ARENE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; DRUG RELEASE; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; REACTION ANALYSIS; STRUCTURE ANALYSIS;

ANIMALS; ANTI-BACTERIAL AGENTS; CALIXARENES; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; MICROBIAL SENSITIVITY TESTS; NALIDIXIC ACID; PHENOLS; PRODRUGS; RATS; WATER;

NEGIBACTERIA; POSIBACTERIA;

EID: 65349158711     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.03.139     Document Type: Article

References (21)

1. Harris, Stephen J., WO Patent 95-IE8 19950124, 1995.
2. Hwang, Kou M.; Ki, You M.; Liu, Su Ying; Lee, T. C.; Choy, W.; Chen, J. WO Patent 9403165, 1985.
3. Hwang, Kou M.; Ki, You M.; Liu, Su Ying; Choy, W.; Chen, J. (Genelab Technologies, Inc. USA) WO Patent 9403164, 1984.
4. Hulmes, D.; Coleman, A.; Aubert-Foucher, E. (CNRS, Fr) WO patent 0007585, 2000.
5. Cornforth J.W., D'Arcy Hart P., Nicholls G.A., Rees R.J.W., and Stock J.A. Br. J. Pharmacol. 10 (1955) 73
6. D'Arcy Hart P., Armstrong A.J., and Brodaty E. Infect. Immun. 64 (1996) 1491
7. Colston M.J., Hailes H.C., Stavropoulos E., Herve A.C., Herve G., Goodworth K.J., Hill A.M., Jenner P., Hart P.D., and Tascon R.E. Infect. Immun. 72 (2007) 6318
8. Loiseau F.A., Hill A.M., and Hii K.K. Tetrahedron 63 (2007) 9947
9. Casnati A., Fabbi M., Pelizzi N., Pochini A., Sansone F., Ungaro R., Di Modugno E., and Tarzia G. Bioorg. Med. Chem. Lett. 6 (1996) 2699
10. Ben Salem A., and Regnouf-de-Vains J.-B. Tetrahedron Lett. 42 (2001) 7033
11. Ben Salem A., and Regnouf-de-Vains J.-B. Tetrahedron Lett. 44 (2003) 6769
12. Korchowiec B., Ben Salem A., Corvis Y., Regnouf de Vains J.-B., Korchowiec J., and Rogalska E. J. Phys. Chem. B 11146 (2007) 13231
13. Gutsche C.D., and Nam K.C. J. Am. Chem. Soc. 110 (1988) 6153
14. 3+/3.
15. CA-SFM. Communiqué 2008 (Edition janvier 2008). http://www.sfm.asso.fr.
16. NCCLS. 2007. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically; approved standard M7-A6, 6th ed. National Committee for Clinical Laboratory Standards, Wayne, Pa, USA. Bacteria were grown in Mueller-Hinton broth (Difco, 275730), or Mueller Hinton agar (Difco, 225250); purity of isolates was checked at the time of every test by examination of colony morphology and Gram staining. For MIC determination experiments, bacteria were inoculated in 96-well U shape microtiter plates to yield a final inoculum of 1 × 105 colony-forming units (CFU)/mL. Then various concentrations of the drugs were added. The cultures were grown for 18-24 h at 35 °C. The resulting bacterial growth was measured with an ELISA plate reader (Multiskan EX, Thermo Electron Corporation, France) at a wavelength of 540 nm.
17. see. Orden J.A., Ruiz-Santa-Quiteria J.A., Garcia S., Cid D., and De La Fuente R. Antimicrob. Agents Chemother. 43 (1999) 510
18. Following approaches described in: Grare, M.; Mourer, M.; Fontanay, S.; Regnouf-de-Vains, J. -B.; Finance, C.; Duval, R. E. 47th Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC), Chicago, USA, 17-20 September 2007.
19. Grare, M.; Massimba Dibama, H.; Lafosse, S.; Ribon, A.; Mourer, M.; Regnouf-de-Vains, J.B.; Finance, C.; Duval, R. E. Clin. Microbiol. Infect., in press.
20. Following approaches described in:. Grare M., Dague E., Mourer M., Regnouf-de-Vains J.-B., Finance C., Duval J.F.L., Duval R.E., and Gaboriaud F. Pathol. Biol. 55 (2007) 465
21. Grare, M.; Lafosse, S.; Regnouf-de-Vains, J. -B.; Finance, C.; Duval, R. E. 48th annual Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC)/ Infectious Diseases Society of America (IDSA), Washington, DC, USA, 25-28 October 2008. (ASM Fellows Travel Grant to Grare M.).