Synthesis and biological activity of 23-hydroxybetulinic acid c-28 ester derivatives as antitumor agent candidates

Molecules

Volumn 17, Issue 8, 2012, Pages 8832-8841

  Bi, Yi ^a   Xu, Jinyi ^b   Sun, Fei ^b   Wu, Xiaoming ^b   Ye, Wencai ^b   Sun, Yijun ^c   Huang, Wenwen ^a  

^a YANTAI UNIVERSITY   (China)

^b CHINA PHARMACEUTICAL UNIVERSITY   (China)

^c Drug Screening Center   (China)

Author keywords

23 hydroxybetulinic acid; Antitumor activity; C 28 ester derivatives; Structure activity relationships

Indexed keywords

23 HYDROXYBETULINIC ACID; 23-HYDROXYBETULINIC ACID; ANTINEOPLASTIC AGENT; CYCLOPHOSPHAMIDE; ESTER; FLUOROURACIL; TRITERPENE;

ANIMAL; ARTICLE; CELL SURVIVAL; DRUG EFFECT; DRUG SCREENING; FEMALE; HUMAN; IC 50; INSTITUTE FOR CANCER RESEARCH MOUSE; MOUSE; SYNTHESIS; TUMOR CELL LINE; TUMOR VOLUME;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; CYCLOPHOSPHAMIDE; ESTERS; FEMALE; FLUOROURACIL; HUMANS; INHIBITORY CONCENTRATION 50; MICE; MICE, INBRED ICR; TRITERPENES; TUMOR BURDEN; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 84865475081     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17088832     Document Type: Article

References (12)

1. Pisha, E.; Chai, H.; Lee, I.S.; Chagwedera, T.E.; Farnsworth, N.R.; Cordell, G.A.; Beecher, C.W.W.; Fong, H.H.S.; Dogglas, K.A.; Brown, D.M.; et al.; Discovery of betulinic acid as a selective inhibitor of human melanoma that functions by induction of apoptosis. Nat. Med. 1995, 1, 1046-1051.
2. Ye, W.C.; Ji, N.-N.; Zhao, S.-X.; Liu, J.-H.; Ye, T.; Mckervey, M.A.; Stevensin, P. Triterpenoids from Pulsatilla chinensis. Phytochemistry 1996, 42, 799-802.
3. Valentina, Z.; Rosanna, S.; Sabina, C.R.; Loredana, C.; Edoardo, M.; Carlo, G.P.; Franca, F. Selective cytotoxicity of betulinic acid on tumor cell lines, but not on normal cells. Cancer Lett. 2002, 175, 17-25.
4. Rita, C.S.; Jorge, A.R.S.; Roldán, C.; Gisela, P.; Silvia, M.; Marta, C. New betulinic acid derivatives induce potent and selective antiproliferative activity through cell cycle arrest at the S phase and caspase dependent apoptosis in human cancer cells. Biochimie 2011, 93, 1065-1075.
5. Baglin, I.; Mitaine-Offer, A.C.; Nour, M.; Tan, K.; Cave, C.; Lacaille-Dubois, M.A. A Review of Natural and Modified Betulinic, Ursolic and Echinocystic Acid Derivatives as Potential Antitumor and Anti-HIV Agents. Mini Rev. Med. Chem. 2003, 3, 525-539.
6. Simone, F.; Klaus, M.D. Sensitization for Anticancer Drug-Induced Apoptosis by Betulinic Acid. Neoplasia 2005, 7, 162-170.
7. Perumal, Y.; Dharmarajan, S. Betulinic Acid and Its Derivatives: A Review on their Biological Properties. Curr. Med. Chem. 2005, 12, 657-666.
8. Rama, M.; Manu, J.; Praveen, R.; Mohammad, J.A.S.; Sanjay, K.S.; Anand, V.; Anand, C.B. Betulinic acid and its derivatives as anti-angiogenic agents. Bioorg. Med. Chem. Lett. 2004, 14, 2181-2184.
9. Heather, J.F.; Tadashi, H.; Gordon, W.G. Synthesis of novel [3,2-b]indole fused oleanolic acids as potential inhibitors of cell proliferation (JM-583FP). ARKIVOC 2002, xii, 38-46.
10. Ji, Z.-N.; Ye, W.-C.; Liu, G.-G.; Wendy, H.W.L. 23-Hydroxybetulinic acid mediated apoptosis is accompanied by decreases in bcl-2 expression and telomerase activity in HL-60 cells. Life Sci. 2002, 72, 1-9.
11. Bi, Y.; Xu, J.-Y.; Wu, X.-M.; Ye, W.-C.; Yuan, S.-T.; Zhang, L.-Y. Synthesis and cytotoxic activity of 17-carboxylic acid modified 23-hydroxy betulinic acid ester derivatives. Bioorg. Med. Chem. Lett. 2007, 17, 1475-1478.
12. Wu, X.M.; Xu, J.Y.; Bi, Y.; Zhou, J.P.; Zhang, L.Y.; Yuan, S.T.; Li, D.; Xu, P. Synthesis method, application and pretaration of 23-hydroxy betulinic acid derivatives. CN 200610040277, 15 November 2006.