Synthesis of novel ring-A fused hybrids of oleanolic acid with capabilities to arrest cell cycle and induce apoptosis in breast cancer cells

European Journal of Medicinal Chemistry

Volumn 74, Issue , 2014, Pages 398-404

  Mallavadhani, Uppuluri Venkata ^a   Vanga, Nagi Reddy ^a   Jeengar, Manish Kumar ^b   Naidu, V G M ^b  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

Anti cancer activity; Apoptosis; Cell cycle arrest; Oleanolic acid; Oleanolic acid hybrids

Indexed keywords

ANTINEOPLASTIC AGENT; BENZYLIDENE DERIVATIVE; DOXORUBICIN; ETOPOSIDE; METHYL 2,3 (1,5 DIPHENYL) 1H PYRAZOLO OLEAN 12 EN 28 OATE; METHYL 2,3 (2 AMINO,4 PHENYL) PYRIMIDINYL OLEAN 12 EN 28 OATE; METHYL 2,3 (4 PHENYL) 1H 2 PYRIMIDONYL OLEAN 12 EN 28 OATE; METHYL 2,3 (4 PHENYL) 1H 2 THIOPYRIMIDONYL OLEAN 12 EN 28 OATE; METHYL 2,3 (5 PHENYL) 4,5 DIHYDRO 1H PYRAZOLO OLEAN 12 EN 28 OATE; METHYL 2,3 (5 PHENYL)ISOXAZOLO OLEAN 12 EN 28 OATE; METHYL 3 BETA HYDROXY OLEAN 12 EN 28 OATE; METHYL 3 OXO 2 BENZYLIDENE OLEAN 12 EN 28 OATE; METHYL 3 OXO OLEAN 12 EN 28 OATE; OLEANOLIC ACID; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CELL STRAIN HT29; CELL STRAIN MCF 7; CELL STRAIN MDA MB 231; CELL STRAIN MDA MB 453; CELL STRAIN ME 180; CELL STRAIN PC 3; CONTROLLED STUDY; DRUG POTENCY; DRUG SYNTHESIS; FLOW CYTOMETRY; HELA CELL; HUMAN; HUMAN CELL; IC 50; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; S PHASE CELL CYCLE CHECKPOINT;

ANTI-CANCER ACTIVITY; APOPTOSIS; CELL CYCLE ARREST; OLEANOLIC ACID; OLEANOLIC ACID HYBRIDS;

APOPTOSIS; BREAST NEOPLASMS; CELL CYCLE; CELL LINE, TUMOR; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MASS SPECTROMETRY; OLEANOLIC ACID;

EID: 84893283159     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.12.040     Document Type: Article

References (17)

1. J. Pollier, and A. Goossens Molecules of interest: oleanolic acid Phytochemistry 77 2012 10 15
2. J. Liu Pharmacology of oleanolic acid and ursolic acid J. Ethanopharmacol. 49 1995 57 68
3. P. Dzubak, M. Hajduch, D. Vydra, A. Hustova, M. Kvasnica, D. Biedermann, L. Markova, M. Urban, and J. Sarek Pharmacological activities of natural triterpenoids and their therapeutic implications Nat. Prod. Rep. 23 2006 394 411
4. J. Chen, J. Liu, L. Zhang, G. Wu, W. Hua, X. Wu, and H. Sun Pentacyclic triterpenes. Part 3: synthesis and biological evaluation of oleanolic acid derivatives as novel inhibitors of glycogen phosphorylase Bioorg. Med. Chem. Lett. 16 2006 2915 2919
5. K. Cheng, J. Liu, and J. Xie Synthesis of oleanolic acid dimmers as inhibitors of glycogen phosphorylase Chem. Biodivers. 7 2010 690 697
6. U.V. Mallavadhani, A. Mahapatra, B. Pattnaik, V. Nagireddy, N. Suri, and A.K. Saxena Synthesis and anti-cancer activity of some novel C-17 analogs of ursolic and oleanolic acids Med. Chem. Res. 22 2013 1263 1269
7. H.J. Finlay, T. Honda, and G.W. Gribble Synthesis of novel [3,2-b] indole fused oleanolic acids as potential inhibitors of cell proliferation Arkivoc 12 2002 38 46
8. U.V. Mallavadhani, A. Mahapatra, S. Sabita Raja, and C. Manjula Antifeedant activity of some pentacyclic triterpene acids and their fatty acid ester analogues J. Agric. Food Chem. 51 2003 1952 1955
9. H. Li, H. Zou, L. Gao, T. Liu, F. Yang, J. li, J. Li, W.-W. Qiu, and J. Tang Synthesis and biological evaluation of oleanolic acid derivatives as novel inhibitors of protein tyrosine phosphatease 1B Heterocycles 85 2012 1117 1139
10. L. Fu, and G.W. Gribble Efficient and scalable synthesis of bardoxolone methyl (CDD)-methyl ester Org. Lett. 15 2013 1622 1625
11. U.V. Mallavadhani, A. Mahapatra, Kaiser Jamil, and P. Srinivasa Reddy Antimicrobial activity of some pentacyclic triterpenes and their 3-O-lipophilic chains Biol. Pharm. Bull. 27 2004 1576 1579
12. U.V. Mallavadhani, Anita K. Panda, and Y.R. Rao Diospyros melanoxylon leaves: a rich source of pentacyclic triterpenes Pharm. Biol. 39 2001 20 24
13. A. Ikuta, and H. Itokawa Triterpenoids of Akebia quinata callus tissue Phytochemistry 25 1986 1625 1628
14. A.G. Gonzalez, J. Amaro, B.M. Fraga, J.G. Luis, J. Fayyos, A. Perales, and M.P. Mendez Minor triterpenes from Orthopterygium huancuy Phytochemistry 23 1984 2079 2080
15. V.G.M. Naidu, U.M. Bandari, A.K. Giddam, K.R.D. Babu, J. Ding, K.S. Babu, B. Ramesh, R.R. Pragada, and P. Gopalakrishnakone Apoptogenic activity of ethyl acetate extract of leaves of Memecylon edule on human gastric carcinoma cells via mitochondrial dependent pathway Asian Pac. J. Trop. Med. 6 2013 337 345
16. D. Ribble, N.B. Goldstein, D.A. Norris, and Y.G. Shellman A simple technique for quantifying apoptosis in 96-well plates BMC Biotechnol. 5 2005 5 12
17. E.-J. Lee, S.-Y. Oh, and M.-K. Sung Luteolin exerts anti-tumor activity through the suppression of epidermal growth factor receptor-mediated pathway in MDA-MB-231 ER-negative breast cancer cells Food Chem. Toxicol. 50 2012 4136 4143