Newly synthesized indolizine derivatives – antimicrobial and antimutagenic properties
-
Petra Olejníková
, Lucia Birošová
Abstract
A series of indolizine derivatives have been synthesized and subjected to antibacterial screening studies. Antibacterial activity of 21 derivatives was investigated against Staphylococcus aureus, Mycobacterium smegmatis, Salmonella typhimurium and Escherichia coli; also, the sensitivity of model yeast Candida parapsilosis and some model filamentous fungi Aspergillus fumigatus, Alternaria alternata, Botrytis cinerea and Microsporum gypseum was tested. Newly synthesized indolizine derivatives have shown selective toxicity to Gram-positive bacteria S. aureus and were also considered to be able to inhibit the acidoresistant rod M. smegmatis. Derivative XXI has shown the highest inhibition effect with the bacteriostatic effect on the cells at the concentration of 25 μg mL−1. The best antifungal activity has been detected in the presence of derivative XIII. Derivative XIII did also affect the morphology of hyphal tips of B. cinerea, which led to enhanced ramification of hyphae. Finally, the antimutagenic activity of derivatives was investigated. Significant antimutagenic activity was registered in case of derivative VIII. The number of induced revertants by mutagen [2-(5-nitrofuryl)acrylic acid] was decreased almost to the level of spontaneous revertants in the lowest applied concentration (50 μg per plate).
References
Brandi, A., Cicchi, S., Cordero, F. M., Frignoli, R., Goti, A., Picasso, S., & Vogel, P. (1995). Assignment of the absolute configuration of natural lentiginosine by synthesis and enzymic assays of optically pure (+) and (-)- enantiomers. Journal of Organic Chemistry, 60, 6806-6812. DOI: 10.1021/jo00126a033.10.1021/jo00126a033Suche in Google Scholar
Clinical Laboratory Standard Institute (2014). Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically; Approved standard-Eight edition, CLSI M7- A9. Wayne, PA, USA: Clinical Laboratory Standard Institute.Suche in Google Scholar
Couture, A., Deniau, E., Grandclaudon, P., Lebrun, S., Leonce, S., Renard, P., & Pfeiffer, B. (2000). First synthesis and pharmacological evaluation of benzoindolizidine and benzoquinolizidine analogues of α-and β-peltatin. Bioorganic & Medicinal Chemistry, 8, 2113-2125. DOI: 10.1016/s0968-0896(00)00130-9.10.1016/S0968-0896(00)00130-9Suche in Google Scholar
Darwish, E. S. (2008). Facile synthesis of heterocycles via 2- picolinium bromide and antimicrobial activities of the products. Molecules, 13, 1066-1078. DOI: 10.3390/molecules130 51066.Suche in Google Scholar
Dudova, B., Hudecova, D., Pokorny, R., Mičkova, M., Palicova, M., Segľa, P., & Melnik, M. (2002). Copper complexes with bioactive ligands. Part II - Antifungal activity. Folia Microbiologica, 47, 225-229. DOI: 10.1007/bf02817642.10.1007/BF02817642Suche in Google Scholar PubMed
Foster, C., Ritchie, M., Selwood, D. L., & Snowden, W. (1995). Synthesis and anti-herpes activity of a series of indolizines. Antiviral Chemistry & Chemotherapy, 6, 289-297.10.1177/095632029500600502Suche in Google Scholar
Gubin, J., Lucchetti, J., Mahaux, J., Nisato, D., Rosseels, G., Clinet, M., Polster, P., & Chatelain, P. (1992). A novel class of calcium-entry blockers: the 1 [[4-(aminoalkoxy)- phenyl]sulfonyl]indolizines. Journal of Medicinal Chemistry, 35, 981-988. DOI: 10.1021/jm00084a002.10.1021/jm00084a002Suche in Google Scholar PubMed
Gundersen, L. L., Negussie, A. H., Rise, F., & Ostby, O. B. (2003). Antimycobacterial activity of 1-substituted indolizines. Archiv der Pharmazie, 336, 191-195. DOI: 10.1002/ ardp.200390019.10.1002/ardp.200390019Suche in Google Scholar PubMed
Gundersen, L. L., Charnock, C., Negussie, A. H., Rise, F., & Teklu, S. (2007). Synthesis of indolizine derivatives with selective antibacterial activity against Mycobacterium tuberculosis. European Journal of Pharmaceutical Sciences, 30, 26-35. DOI: 10.1016/j.ejps.2006.09.006.10.1016/j.ejps.2006.09.006Suche in Google Scholar PubMed
Gupta, S. P., Mathur, A. N., Nagappa, A. N., Kumar, D., & Kumaran, S. (2003). A quantitative structure-activity relationship study on a novel class of calcium-entry blockers: 1-[{4-(aminoalkoxy) phenyl}sulphonyl]indolizines. European Journal of Medicinal Chemistry, 38, 867-873. DOI: 10.1016/j.ejmech.2003.08.001.10.1016/j.ejmech.2003.08.001Suche in Google Scholar PubMed
Hazra, A., Mondal, S., Maity, A., Naskar, S., Saha, P., Paira, R., Sahu, K. B., Paira, P., Ghosh, S., Sinha, C., Samanta, A., Banerjee, S., & Mondal, N. B. (2011). Amberlite- IRA-402 (OH) ion exchange resin mediated synthesis of indolizines, pyrrolo[1,2-a]quinolines and isoquinolines: Antibacterial and antifungal evaluation of the products. European Journal of Medicinal Chemistry, 46, 2132-2140. DOI: 10.1016/j.ejmech.2011.02.066.10.1016/j.ejmech.2011.02.066Suche in Google Scholar PubMed
Hema, R., Parthasarathi, V., Sarkunam, K., Nallu, M., & Linden, A. (2003). 3-(4-Chlorobenzoyl)-7-(N, N-dimethylamino)-1-phenylindolizine and 3-(2,4-dichlorobenzoyl)-7-(N,N-dimethylamino)-1-phenylindolizine. Acta Crystallographica Section C: Crystal Structure Communications, 59, o703- o705. DOI: 10.1107/s0108270103023540.10.1107/S0108270103023540Suche in Google Scholar PubMed
Hempel, A., Camerman, N., Mastropaolo, D., & Camerman, A. (1993). Glucosidase inhibitors: structures of deoxynojirimycin and castanospermine. Journal of Medicinal Chemistry, 36, 4082-4086. DOI: 10.1021/jm00077a012.10.1021/jm00077a012Suche in Google Scholar
Hudecova, D., Varečka, Ľ., Vollek, V., & Betina, V. (1994). Growth and morphogenesis of Botrytis cinerea. Effects of exogenous calcium ions, calcium channel blockers and cyclosporin A. Folia Microbiologica, 39, 269-275. DOI: 10.1007/bf02814311.10.1007/BF02814311Suche in Google Scholar
Jorgensen, A. S., Jacobsen, P., Christiansen, L. B., Bury, P. S., Kanstrup, A., Thorpe, S. M., Bain, S., Naerum, L., &Wassermann, K. (2000). Synthesis and pharmacology of a novel pyrrolo [2,1,5-cd] indolizine (NNC 45-0095), a high affinity non-steroidal agonist for the estrogen receptor. Bioorganic & Medicinal Chemistry Letters, 10, 399-402. DOI: 10.1016/s0960-894x(00)00015-9.10.1016/S0960-894X(00)00015-9Suche in Google Scholar
Koul, A., Choidas, A., Treder, M., Tyagi, A. K., Drlica, K., Singh, Y., & Ullrich, A. (2000). Cloning and characterization of secretory tyrosine fosfatases of Mycobacterium tuberculosis. Journal of Bacteriology, 182, 5425-5432. DOI: 10.1128/jb.182.19.5425-5432.2000.10.1128/JB.182.19.5425-5432.2000Suche in Google Scholar
Kubo, A., Nakai, T., Koizumi, Y., Kitahara, Y., Saito, N., Mikami, Y., Yazava, K., & Uno, J. (1996). A Synthesis of the derivatives of 1,2,3,5,10,10a-hexahydrobenz[f]indoline-6,9-dione having antifungal activity as a simple model of Saframycin A. Heterocycles, 42, 195-211. DOI: 10.3987/com-94-S5-1.10.3987/COM-94-S5-1Suche in Google Scholar
Marchalin, S., Decroix, B., & Morel, J. (1993). Synthesis of indolizine-6,9-diones annelated to a thiophene ring. Acta Chemica Scandinavica, 47, 287-291. DOI: 10.3891/acta. chem.scand.47-0287.Suche in Google Scholar
Marchalin, S., Szemes, F., Bar, N., & Decroix, B. (1999). Synthesis of enantiopure (S)-thieno[f]indolizidines. Heterocycles, 50, 445-452. DOI: 10.3987/com-98-s(h)10.10.3987/COM-98-S(H)10Suche in Google Scholar
Maron, D. M., & Ames, B. N. (1983). Revised methods for the Salmonella mutagenicity test. Mutation Research, 113, 173-215. DOI: 10.1016/0165-1161(83)90010-9.10.1016/0165-1161(83)90010-9Suche in Google Scholar
Mitsumori, T., Bendikov, M., Dautel, O., Wudl, F., Shioya, T., Sato, H., & Sato, Y. (2004). Synthesis and properties of highly fluorescent indolizino [3,4,5-ab] isoindoles. Journal of the American Chemical Society, 126, 16793-16803. DOI: 10.1021/ja049214x.10.1021/ja049214xSuche in Google Scholar
Nasir, A. I., Gundersen, L. L., Rise, F., Antonsen, O., Kristensen, T., Langhelle, B., Bast, A., Custers, I., Haenen, G. R. M. M., & Wikstr¨om, H. (1998). Inhibition of lipid peroxidation mediated by indolizines. Bioorganic & Medicinal Chemistry Letters, 8, 1829-1832. DOI: 10.1016/s0960-894x(98)00313-8.10.1016/S0960-894X(98)00313-8Suche in Google Scholar
Olejnikova, P., Kurucova, M., Švorc, Ľ., & Marchalin, Š. (2013). Induction of resistance in Mycobacterium smegmatis. Canadian Journal of Microbiology, 59, 126-129. DOI: 10.1139/cjm-2012-0438.10.1139/cjm-2012-0438Suche in Google Scholar PubMed
Pearson, W. H., & Guo, L. (2001). Synthesis and mannosidase inhibitory activity of 3-benzyloxymethyl analogs of swainsonine. Tetrahedron Letters, 42, 8267-8271. DOI: 10.1016/s0040-4039(01)01777-4.10.1016/S0040-4039(01)01777-4Suche in Google Scholar
Šáfař, P., Žužiová, J., Bobošiková, M., Marchalin, Š., Prόnayová, N., Comesse, S., & Daïch, A. (2009a). Synthesis and reductive desulfurization of chiral non-racemic benzothienoindolizines. An efficient approach to a novel bioactive tylophorine alkaloid analogue and 6-phenylindolizidine. Tetrahedron: Asymmetry, 20, 2137-2144. DOI: 10.1016/j.tetasy. 2009.08.010.Suche in Google Scholar
Šafář, P., Žužiová, J., Marchalin, Š., Tόthová, E., Prόnayová, N., Švorc, Ľ., Vrábel, V., & Daïch, A. (2009b). Highly diastereoselective approach to novel phenylindolizidinols via benzothieno analogues of tylophorine based on reductive desulfurization of benzo[b] thiophene. Tetrahedron: Asymmetry, 20, 626-634. DOI: 10.1016/j.tetasy.2009.02.042.10.1016/j.tetasy.2009.02.042Suche in Google Scholar
Sonnenschein, H., Hennrich, G., Resch-Genger, U., & Schulz, B. (2000). Fluorescence and UV/Vis spectroscopic behavior of novel biindolizines. Dyes and Pigments, 46, 23-27. DOI: 10.1016/s0143-7208(00)00032-2.10.1016/S0143-7208(00)00032-2Suche in Google Scholar
Teklu, S., Gundersen, L. L., Larsen, T., Malterud, K. E., & Rise, F. (2005). Indolizine 1-sulfonates as potent inhibitors of 15-lipoxygenase from soybeans. Bioorganic & Medicinal Chemistry, 13, 3127-3139. DOI: 10.1016/j.bmc.2005.02.056.10.1016/j.bmc.2005.02.056Suche in Google Scholar PubMed
Toyota, M., Komori, C., & Ihara, M. (2000). A concise formal total synthesis of mappicine and nothapodytine B via an intramolecular hetero Diels-Alder reaction. Journal of Organic Chemistry, 65, 7110-7113. DOI: 10.1021/jo000816i.10.1021/jo000816iSuche in Google Scholar PubMed
Vaught, J. L., Carson, J. R., Carmosin, R. J., Blum, P. S., Persico, F. J., Hageman, W. E., Shank, R. P., & Raffa, R. B. (1990). Antinociceptive action of McN-5195 in rodents: a structurally novel (indolizine) analgesic with a nonopioid mechanism of action. Journal of Pharmacology and Experimental Therapeutics, 255, 1-10.Suche in Google Scholar
Vemula, V. R., Vurukonda, S., & Bairi, C. K. (2011). Indolizine derivatives: recent advances and potential pharmacological activities. International Journal of Pharmaceutical Sciences Review & Research, 11, 159-163.Suche in Google Scholar
Vlahovici, A., Andrei, M., & Drută, I. (2002). A study of the dimethyl-3-benzoyl-5-(2′-pyridyl)-indolizine-1,2-dicarboxylate exciplexes with alcohols. Journal of Luminescence, 96, 279-285. DOI: 10.1016/s0022-2313(01)00226-5. Wavefunction (2006). Spartan’06 [computer software]. Irvine, CA, USA: Wavefunction.Suche in Google Scholar
Weide, T., Arve, L., Prinz, H., Waldmann, H., & Kessler, H. (2006). Substituted indolizine-1-carbonitrile derivatives as phosphatase inhibitors. Bioorganic & Medical Chemistry Letters, 16, 59-63. DOI: 10.1016/j.bmcl.2005.09.051 10.1016/j.bmcl.2005.09.051Suche in Google Scholar PubMed
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- An electrochemical sensor for sensitive determination of nitrites based on Ag–Fe3O4–graphene oxide magnetic nanocomposites
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