QUANTITATIVE RELATIONSHIP OF ELECTRONIC STRUCTURE AND INHIBITION ACTIVITY OF CURCUMIN ANALOGS ON ETHOXYRESORUFIN o-DEALKYLATION (EROD) REACTION

https://doi.org/10.22146/ijc.21717

Harno Dwi Pranowo(1*), Iqmal Tahir(2), Ajidarma Widiatmoko(3)

(1) Austrian-Indonesian Centre for Computational Chemistry, Faculty of Mathematics and Natural Sciences Gadjah Mada University, Sekip Utara, Yogyakarta, Indonesia 55281
(2) Austrian-Indonesian Centre for Computational Chemistry, Faculty of Mathematics and Natural Sciences Gadjah Mada University, Sekip Utara, Yogyakarta, Indonesia 55281
(3) Austrian-Indonesian Centre for Computational Chemistry, Faculty of Mathematics and Natural Sciences Gadjah Mada University, Sekip Utara, Yogyakarta, Indonesia 55281
(*) Corresponding Author

Abstract


Electronic structure and inhibition activity relationship study of curcumin analogs has been established for 29 curcumin analogs on Ethoxyresorufin O-Dealkylation (EROD) reaction using atomic net charge descriptor based on AM1 semiempirical calculations. The QSAR (Quantitative Structure and Activities Relationships) equation model was determined by statistical parameter from multiple regression analysis and leave-one-out cross validation method. The best QSAR equation was described:

log1/IC50 = (36.726±9.028) + (92.368±27.591)qC4 + (260.114±46.029)qC7

               + (45.406±9.994)qC10 – (9.287±4.034)qC15 – (8.344±3.685)qC17

               – (16.993±3.457)qC18 – (237.490±46.644)qO1 + (293.293±48.749)qO2


Keywords


curcumin; QSAR; descriptor; atomic net charge; semiempirical methods

Full Text:

Full Text PDF


References

[1] Sardjiman, 2000, Synthesis of Some Series of Curcumin Analogs, Antioxidative, Antiinflamatory, Antibacterial Activities and Qualitative Structure-Activity Relationships, Dissertasi, Universitas Gadjah Mada, Yogyakarta

[2] Sharma, O. P., 1976, Biochem. Pharmacol., 25, 1811 – 1812

[3] Oetari, R. A., 1997, Interaction between Curcumin and Curcumin Analogues and Cytochrome P450: Molecular and Structure-Activity Relationships Studies, Dissertasi, Universitas Gadjah Mada, Yogyakarta.

[4] Purcell, W. P., 1974, Quantitative Structure-Activity Relationship, in Bergman, E. D., Pulman, B., Mol. Quant. Pharm., Reidel Publishing Company.

[5] Kubinyi, H., 1993, QSAR : Hansch Analysis and Related Approach, VCH Verlagsgessellschaft, Weinheim.

[6] Balbes, L. M., and Mascarella, S. W., 1994, A Perspective of Modern Methods in Computer-Aided Drug Design, in Lipkowitz, K. B., Boyd, D. B., Rev. Comp. Chem., Volume V, VCH Publisher, New York.

[7] Tahir, I., Setiaji, B. and Alim, S.A., 2001, Berkala Ilmiah MIPA, XI (1), 1-29

[8] Bhattacharjee, A. K., Kyle, D. E., Vennerstrom, J. L., and Milhous, W. K., 2002, J. Chem. Inf. Comput. Sci., 42, 1212 – 1220.

[9] Cramer, R. D., Patterson, D. E., and Bunce, J. D., 1988, Bull. Korean. Chem. Soc., 22, 388-394.

[10] Lee, K. W., Kwon, S. Y., Hwang, S. L., and Kim, H. J., 1996, Bull. Korean Chem. Soc., 17, 147-152.

[11] Karelson, M., Lobanov, V. P., and Katritzki, A. R., 1996, Chem. Rev., 96, 1027 – 1043

[12] Tahir, I., Setiaji, B., Wahyuningsih, T.D., Raharjo, T.J., and Noegrohati, S., 2002, Gama Sains, IV, 2, 135-141.

[13] Mustofa, Tahir, I., and Jumina, 2002, Indo. J. Chem., 2 (2), 91-96.

[14] Mudasir, Putri, I.D.P.M., and Tahir, I., 2003, Indo. J. Chem., 3 (1), 39-47

[15] Tahir, I., Wijaya, K., Widianingsih, D., and Purwono. B., 2003, Indo. J. Chem., 3 (1), 48-54

[16] Mustofa, Yapii, A.D., Valentin, A., and Tahir, I., 2003, Berkala Ilmu Kedokteran, 35 (2), 67-74

[17] Istyastono, E.P., Martono, S., Pranowo, H.D., and Tahir, I., 2003, Indo. J. Chem., 3 (3), 179-186

[18] Yuliana, Pranowo, H.D., Jumina, and Tahir, I., 2004, Indo. J. Chem., 4 (1), 68-75

[19] Tahir, I., Mudasir, Yulistia, I., and Mustofa, 2005, Indo. J. Chem., 5 (3), 255-260

[20] Istiyastono, E.P., Supardjan, and Pranowo, H.D., 2003, Majalah Farmasi Indonesia 14(3), 107-113.



DOI: https://doi.org/10.22146/ijc.21717

Article Metrics

Abstract views : 2271 | views : 5674


Copyright (c) 2010 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 

Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web Analytics View The Statistics of Indones. J. Chem.