Pro-apoptotic properties of parthenin analogs: a quantitative structure–activity relationship study
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- 作者：Rukmankesh Mehra (1)
Amit Nargotra (1)
Bhahwal A. Shah (2)
Subhash C. Taneja (2)
Ram A. Vishwakarma (1)
Surrinder Koul (2) - 关键词：Apoptotic activity ; Genetic function approximation ; Parthenin analogs ; QSAR ; Regression
- 刊名：Medicinal Chemistry Research
- 出版年：2013
- 出版时间：May 2013
- 年：2013
- 卷：22
- 期：5
- 页码：2303-2311
- 全文大小：528KB
- 参考文献：1. Accelrys Inc. Cerius2 modeling environment, release 4.10 (2005) Accelrys Software Inc., San Diego
2. Deswal S, Roy N (2006) Quantitative structure activity relationship studies of?aryl heterocycle-based thrombin inhibitors. Eur J Med Chem 41(11):1339-346 CrossRef
3. Deswal S, Roy N (2007) A novel range based QSAR study of human neuropeptide Y (NPY) Y5 receptor inhibitors. Eur J Med Chem 42(4):463-70 CrossRef
4. Durdagi S, Supuran CT, Strom TA, Doostdar N, Kumar MK, Barron AR, Mavromoustakos T, Papadopoulos MG (2009) In silico drug screening approach for the design of magic bullets: a successful example with anti-HIV fullerene derivatized amino acids. J Chem Inf Model 49:1139-143 CrossRef
5. Durrant JD, Urbaniak MD, Ferguson MAJ, McCammon JA (2010) Computer-aided identification of / Trypanosoma brucei Uridine diphosphate galactose 4-epimerase inhibitors: toward the development of novel therapies for African sleeping sickness. J Med Chem 53(13):5025-032 CrossRef
6. Estrada E, Uriarte E (2001) Recent advances on the role of topological indices in drug discovery research. Curr Med Chem 8:1573-588 CrossRef
7. Fernández A, Sanguino A, Peng Z, Crespo A, Ozturk E, Zhang X, Wang S, Bornmann W, Berestein GL (2007) Rational drug redesign to overcome drug resistance in cancer therapy: imatinib moving target. Cancer Res 67:4028-033 CrossRef
8. Golbraikh A, Tropsha A (2002) Beware of / q 2. J Mol Graph Model 20(4):269-76 CrossRef
9. Gregorio CD, Kier LB, Hall LH (1998) QSAR modeling with the electrotopological state indices: corticosteroids. J Comput Aided Mol Des 12:557-61 CrossRef
10. Haseler WH (1976) / Parthenium hysterophorus L. in Australia. Pest Artic News Summ 22:515-17
11. Herz W, Watanabe H, Miyazaki M, Kishida Y (1962) The structures of parthenin and ambrosin. J Am Chem Soc 84(13):2601-610 CrossRef
12. Jaiswal M, Khadikar PV, Scozzafava A, Supuran CT (2004) Carbonic anhydrase inhibitors: the first QSAR study on inhibition of tumor-associated isoenzyme IX with aromatic and heterocyclic sulfonamides. Bioorg Med Chem Lett 14:3283-290 CrossRef
13. Katritzky AR, Gordeeva E (1993) Traditional topological indexes vs electronic, geometrical, and combined molecular descriptors in QSAR/QSPR research. J Chem Inf Comput Sci 33(6):835-57 CrossRef
14. Kier LB, Hall LH (1976) Molecular connectivity in chemistry and drug research. Academic Press, New York
15. Kier LB, Hall LH (1986) Molecular connectivity in structure–activity analysis. Wiley Publishers, London
16. Kier LB, Hall LH (1990) An electrotopological-state index for atoms in molecules. Pharm Res 7:801-07 CrossRef
17. Leonard J, Roy K (2006) On selection of training and test sets for the development of predictive QSAR models. QSAR Comb Sci 25:235-51 CrossRef
18. Luo J, Solimini NL, Elledge SJ (2009) Principles of cancer therapy: oncogene and non-oncogene addiction. Cell 136:823-37 CrossRef
19. Mehta RG, Pezzuto JM (2002) Discovery of chemopreventive agents from natural products: from plants to prevention. Curr Oncol Rep 4:478-86 CrossRef
20. Melagraki G, Afantitis A, Sarimveis H, Markopoulou OI, Supuran CT (2006) QSAR study on / para-substituted aromatic sulfonamides as carbonic anhydrase II inhibitors using topological information indices. Bioorg Med Chem 14(4):1108-114 CrossRef
21. Mew D, Blaza F, Towers GHN, Levy JG (1982) Antitumor effects of the sesquiterpene lactone parthenin isolated from / Parthenium hysterophorus. J Med Plant Res 45:23-7 CrossRef
22. Nargotra A, Sharma S, Koul JL, Sangwan PL, Khan IA, Kumar A, Taneja SC, Koul S (2009) Quantitative structure activity relationship (QSAR) of piperine analogs for bacterial NorA efflux pump inhibitors. Eur J Med Chem 44(10):4128-135 CrossRef
23. Paudel VR (2009) / Parthenium hysterophorus L., a noxious invasive weed. Bot Orient J Plant Sci 6:85-2
24. Ramesh C, Harakishore K, Murty USN, Das B (2003) Analogues of Parthenin and their antibacterial activity. ARKIVOC (ix):126-32
25. Rodriquez E, Toshika H, Mabry TJ (1971) Sesquiterpene lactone chemistry of the genus / Parthenium (compositae). Phytochemistry 10:1145-154 CrossRef
26. Rogers D, Hopfinger AJ (1994) Application of genetic function approximation to quantitative structure–activity relationships and quantitative structure–property relationships. J Chem Inf Comput Sci 34(4):854-66 CrossRef
27. Rose K, Hall LH, Kier LB (2002) Modeling blood–brain barrier partitioning using the electrotopological state. J Chem Inf Comput Sci 42(3):651-66 CrossRef
28. Roy P, Roy K (2008) On some aspects of variable selection for partial least squares regression models. QSAR Comb Sci 27(3):302-13 CrossRef
29. Shah BA, Kour R, Gupta P, Kumar A, Sethi VK, Andotra SS, Singh J, Saxena AK, Taneja SC (2009) Structure–activity relationship (SAR) of parthenin analogues with pro-apoptotic activity: development of novel anti-cancer leads. Bioorg Med Chem Lett 19(15):4394-398 CrossRef
30. Shapiro S, Guggenheim B (1998) Inhibition of oral bacteria by phenolic compounds. Part 1. QSAR analysis using molecular connectivity. Quant Struct–Act Relatsh 17:327-37 CrossRef
31. Shi W, Shen Q, Kong W, Bao-Xian Y (2007) QSAR analysis of tyrosine kinase inhibitor using modified ant colony optimization and multiple linear regression. Eur J Med Chem 42(1):81-6 CrossRef
32. Soudy R, Gill A, Sprules T, Lavasanifar A, Kaur K (2011) Proteolytically stable cancer targeting peptides with high affinity for breast cancer cells. J Med Chem 54:7523-534 CrossRef
33. Spainhour CB (2005) Natural products. In: Gad SC (ed) Drug discovery handbook. Wiley, Hoboken
34. Tamado T, Schütz W, Milberg P (2002) Germination ecology of the weed / Parthenium hysterophorus in eastern Ethiopia. Ann Appl Biol 140:263-70 CrossRef
35. Towers GHN, Rodriguez E, Bennett FD, Rao PVS (1977) Biology and chemistry of / Parthenium hysterophorus L., A problem weed in India. J Sci Ind Res 36(12):672-84
36. Vanhoecke BW, Depypere HT, Beyter AD, Sharma SK, Parmar VS, Keukeleire DD, Bracke ME (2005) New anti-invasive compounds: results from the Indo-Belgian screening program. Pure Appl Chem 77:65-4 CrossRef - 作者单位：Rukmankesh Mehra (1)
Amit Nargotra (1)
Bhahwal A. Shah (2)
Subhash C. Taneja (2)
Ram A. Vishwakarma (1)
Surrinder Koul (2)
1. Discovery Informatics Unit, Indian Institute of Integrative Medicine (CSIR), Jammu, 180001, Jammu and Kashmir, India
2. Bioorganic Chemistry Section, Indian Institute of Integrative Medicine (CSIR), Jammu, 180001, Jammu and Kashmir, India
文摘
The pro-apoptotic activity of 37 parthenin analogs was quantitatively related to their structures by carrying out quantitative structure–activity relationship study employing genetic function approximation algorithm. Five descriptors were found to be important contributors toward the pro-apoptotic activity of the said compound series. The statistical significance of the model was authenticated with a very good correlation and cross-validation correlation parameter (r 2?=?0.9 and q 2?=?0.839). The model was also validated for leave-25?%-out cross-validation test and external prediction criteria and was found to be well within the acceptable range. The model would be very useful for designing and lead optimization of anticancer compounds and also for prediction of activity of new compounds in this series.