Rational design of novel anti-microtubule agent (9-azido-noscapine) from quantitative structure activity relationship (QSAR) evaluation of noscapinoids

Journal of Biomolecular Screening

Volumn 16, Issue 9, 2011, Pages 1047-1058

  Santoshi, Seneha ^a   Naik, Pradeep K ^b   Joshi, Harish C ^b  

^a JAYPEE UNIVERSITY OF INFORMATION TECHNOLOGY   (India)

^b EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

antitumor activity; azido noscapine; noscapinoids; QSAR

Indexed keywords

9 AZIDO NOSCAPINE; NOSCAPINE; NOSCAPINOID; UNCLASSIFIED DRUG;

ACUTE LYMPHOBLASTIC LEUKEMIA; ANTINEOPLASTIC ACTIVITY; ARTICLE; CRYSTAL STRUCTURE; GENE FUNCTION; GEOMETRY; HUMAN; HUMAN CELL; IC 50; LEUKEMIA CELL; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG DESIGN; HUMANS; MICROTUBULES; MODELS, MOLECULAR; NOSCAPINE; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; REPRODUCIBILITY OF RESULTS;

EID: 80053480531     PISSN: 10870571     EISSN: 1552454X     Source Type: Journal    
DOI: 10.1177/1087057111418654     Document Type: Article

References (15)

1. Wulff O. Prolonged Antitussive Action of a Resin-Bound Noscapine Preparation. J. Pharma. Sci. 1965 ; 54: 1058-1060
2. Ye K., Ke Y., Keshava N., Shanks J., Kapp J. A., Tekmal R. R., Petros J., Joshi H. C. Opium Alkaloid Noscapine Is an Antitumor Agent That Arrests Metaphase and Induces Apoptosis in Dividing Cells. Proc. Natl. Acad. Sci. U. S. A. 1998 ; 95: 2280-2286
3. Zhou J., Panda D., Landen J. W., Wilson L., Joshi H. C. Minor Alteration of Microtubule Dynamics Causes Loss of Tension across Kinetochore Pairs and Activates the Spindle Checkpoint. J. Biol. Chem. 2002 ; 277: 17200-17208 (Pubitemid 34967753)
4. Zhou J., Gupta K., Aggarwal S., Aneja R., Chandra R., Panda D., Joshi H. C. Brominated Derivatives of Noscapine Are Potent Microtubule-Interfering Agents That Perturb Mitosis and Inhibit Cell Proliferation. Mol. Pharmacol. 2003 ; 63: 799-807 (Pubitemid 36368986)
5. Aneja R., Liu M., Yates C., Gao J., Dong X., Zhou B., Vangapandu S. N., Zhou J., Joshi H. C. Multidrug Resistance-Associated Protein-Over Expressing Teniposide-Resistant Human Lymphomas undergo Apoptosis by a Tubulin-Binding Agent. Cancer Res. 2008 ; 68: 1495-1503 (Pubitemid 351346858)
6. Aneja R., Vangapandu S. N., Lopus M., Viswesarappa V. G., Dhiman N., Verma A., Chandra R., Panda D., Joshi H. C. Synthesis of Microtubule-Interfering Halogenated Noscapine Analogs Perturb Mitosis in Cancer Cells followed by Cell Death. Biochem. Pharmacol. 2006 ; 72: 415-426 (Pubitemid 44061746)
7. Aneja R., Vangapandu S. N., Joshi H. C. Synthesis and Biological Evaluation of a Cyclic Ether Fluorinated Noscapine Analog. Bioorg. Med. Chem. 2006 ; 14: 8352-8358 (Pubitemid 44667552)
8. Aneja R., Vangapandu S. N., Lopus M., Chandra R., Panda D., Joshi H. C. Development of a Novel Nitro-Derivative of Noscapine for the Potential Treatment of Drug-Resistant Ovarian Cancer and T-Cell Lymphoma. Mol. Pharmacol. 2006 ; 69: 1801-1809 (Pubitemid 43894296)
9. Aggarwal S., Ghosh N. N., Aneja R., Joshi H. C., Chandra R. A Convenient Synthesis of Aryl-Substituted N-Carbamoyl/N-Thiocarbamoyl Narcotine and Related Compounds. Helvetica Chimica Acta. 2002 ; 85: 2458-2462 (Pubitemid 34984179)
10. Friedman J. Multivariate Adaptive Regression Splines. Stanford, CA: Stanford University ; 1988 :
11. Naik P. K., Alam A., Malhotra A., Rizvi O. Molecular Modeling and Structure-Activity Relationship of the Podophyllotoxin and Its Congeners. J. Biomol. Screen. 2010 ; 15: 528-540
12. Naik P. K., Sindhura S. T., Singh H. Quantitative Structure-Activity Relationship (QSAR) of the Insecticides: The Development of Predictive In Vivo Insecticide Activity Models. SAR QSAR Env. Res. 2009 ; 20: 551-556
13. Cicero D. O., Barbato G., Bazzo R. NMR Analysis of Molecular Flexibility in Solution: A New Method for the Study of Complex Distributions of Rapidly Exchanging Conformations. J. Am. Chem. Soc. 1995 ; 117: 1027-1033
14. Thanikaivelan P., Subramanian V., Rao J. R., Nair B. U. Application of Quantum Chemical Descriptor in Quantitative Structure Activity and Structure Property Relationship. Chem. Phys. Lett. 2000 ; 323: 59-70
15. Ertl P., Rohde B., Selzer P. Fast Calculation of Molecular Polar Surface Area as a Sum of Fragment-Based Contributions and Its Application to the Prediction of Drug Transport Properties. J. Med. Chem. 2000 ; 43: 3714-3717