Experimental and modelling studies on antifungal compounds

• Authors: Mukesh Doble , K. Kumar
• Languages of publication: EN

Abstracts

EN

Antifungal activity of organic compounds (aromatic, salicylic derivatives, cinnamyl derivatives etc) on Fusarium Rosium (14 compounds) and Aspergillus niger (17 compounds) was studied and QSAR models were developed relating molecular descriptors with the observed activity. Back propagation Neural Network models and single and multiple regression models were tested for predicting the observed activity. The data fit as well as the predictive capability of the neural network models were satisfactory (R2 = 0.84, q2 = 0.73 for Fusarium Rosium and R2 = 0.75, q2 = 0.62 for Aspergillus niger). The descriptors used in the network for the former were X4 (connectivity) and Jhetv (topological); and TIC1 (information) and SPI (topological) for the latter fungus. Antifungal activities of these organic compounds were generally lower against the latter than with the former fungus.

Keywords

EN

QSAR; neural network; structural descriptor; Aspergillus niger; Fusarium Rosium

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2006
• Volume: 4
• Issue: 3
• Pages: 428-439

Dates

published

1 - 9 - 2006

online

1 - 9 - 2006

Contributors

author

Mukesh Doble

• Department of Biotechnology, Indian Institute of Technology, Madras, Chennai, 600036, India

author

K. Kumar

• Department of Chemistry, SSS Institute of Higher Learning, Prasanthi Nilayam, Andhra Pradesh, India

References

• [1] G. Sumbali: The Fungi, Alpha Science International, Harrow, Middlesex, 2005.
• [2] G.N. Agrios: Plant Pathology, 3rd ed., Academic Press, Inc, San Diego, 1988.
• [3] S.Y. Choi, J.H. Shin, C.K. Ryu, K.Y. Nam, K.T. No and H.Y.P. Cho: “The development of 3D-QSAR study and recursive partitioning of heterocyclic quinone derivatives with antifungal activity”, Bioorganic & Medicinal Chemistry, Vol. 14, (2006), pp. 1608–1617. http://dx.doi.org/10.1016/j.bmc.2005.10.010[Crossref]
• [4] J.K. Rugutt, A.N. Ngigi, K.J. Rugutt and P.K. Ndalut: “Native Kenyan plants as possible alternatives to methyl bromide in soil fumigation”, Phytomedicine, article in press.
• [5] Y.Y. Cheng and H. Yuan: “Quantitative study of electrostatic and steric effects on physicochemical property and biological activity”, J. Mol. Graph. Modelling, Vol. 24, (2005), pp. 219–226. http://dx.doi.org/10.1016/j.jmgm.2005.08.005[Crossref]
• [6] R. Crebelli, C. Andreoli, A. Carere, G. Conti, L. Conti, M.C. Ramusino and R. Benigni: “The induction of mitotic chromosome malsegregation in Aspergillus nidulans. quantitative structure activity relationship (QSAR) analysis with chlorinated aliphatic hydrocarbons”, Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis, Vol. 266, (1992), pp. 117–134 http://dx.doi.org/10.1016/0027-5107(92)90179-6[Crossref]
• [7] W. Wiktorowicz, M. Markuszewsk, J. Krysinski and R. Kaliszan: “Quantitative structure-activity relationships study of a series of imidazole derivatives as potential new antifungal drugs”, Acta Pol. Pharm., Vol. 59, (2002), pp 295–306. [PubMed]
• [8] Y.S. Prabhakar, P. Jain, Z.K. Khan, W. Haq and S.B. Katti: “Synthesis and QSAR Studies on the Antifungal Activity of 2,3,4-Substituted Thiazolidines”, QSAR & Combinatorial Science, Vol. 22, (2003), pp 456–465. http://dx.doi.org/10.1002/qsar.200390035[Crossref]
• [9] J. Turner, D.A. Stafford and D.E. Hughes: “The reduction of three plant pathogens (Fusarium, Corynebacterium and Globodera) in anaerobic digesters” Agricultural Wastes, Vol. 6, (1983), pp. 1–11. http://dx.doi.org/10.1016/0141-4607(83)90002-1[Crossref]
• [10] R. Todeschini, M. Lasagni and E. Marengo: “New Molecular Descriptors for 2D-and 3D-structures”, J. Chemom., Vol. 8, (1994), pp 263–273. http://dx.doi.org/10.1002/cem.1180080405[Crossref]
• [11] R. Todeschini and V. Consonni: Handbook of Molecular Descriptors, Wiley-VCH, Weinheim, Germany, 2000.
• [12] M. Karelson: Molecular Descriptors in QSAR/QSPR, Wiley Interscience, New York, USA, 2000.
• [13] L.B. Kier and L.H. Hall: Molecular Structure Description. The Electrotopological State, Academic Press, New York, 1999.
• [14] J. Devillers and A.T. Balaban (Ed.): Topological Indices and Related Descriptors in QSAR and QSPR, Gordon and Breach, The Netherlands, 1999.
• [15] L.B. Kier and L.H. Hall: Molecular Connectivity in Structure-Activity Analysis, RSP-Wiley, Chichetser (UK), 1986.
• [16] M. Randic: “Novel Shape Descriptors for Molecular Graphs”, J. Chem. Inf. Compuer Sci., Vol. 41, (2001), pp. 607–613. http://dx.doi.org/10.1021/ci0001031[Crossref]
• [17] A.T. Balaban: “Highly Discriminating Distance-Based Topological Index”, Chem. Phys. Lett., Vol. 89, (1982), pp. 399–406 http://dx.doi.org/10.1016/0009-2614(82)80009-2[Crossref]
• [18] S. Gupta, M. Singh and A.K. Madan: “Superpendentic index: a novel topological descriptor for predicting biological activity”, J. Chem. Inf. Comp. Sci., Vol. 39, (1999), pp 272–277. http://dx.doi.org/10.1021/ci980073q[Crossref]
• [19] V.R. Magnuson, D.K. Harriss and S.C. Basak: “Information indices”, In: R.B. King (Ed.): Studies in Physical and Theoretical Chemistry, Elsevier, The Netherlands, Amsterdam, 1983, pp. 178–191.
• [20] R. Benigni, L. Passerini and A. Rodomonte: “Structure-activity relationships for the mutagenicity and carcinogenicity of simple and - unsaturated aldehydes”, Environmental and Molecular Mutagenesis, Vol. 42, (2003), pp. 136–143. http://dx.doi.org/10.1002/em.10190[Crossref]
• [21] D. T. Stanton and P. C. Jurs: “Development and use of charged partial surface area structural descriptors in computer-assisted quantitative structure-property relationship studies”, Anal Chem., Vol. 62, (1990), pp. 2323–2329. http://dx.doi.org/10.1021/ac00220a013[Crossref]
• [22] R. Gozalbes, J.P. Doucet and F. Derouin: “Application of Topological Descriptors in QSAR and Drug Design: History and New Trends”, Current Drug Targets - Infectious Disorders, Vol. 2, (2002), pp. 93–102. http://dx.doi.org/10.2174/1568005024605909[Crossref]

Identifiers

DOI

10.2478/s11532-006-0022-4