An efficient conversion of taxinine to taxinine NN-1, an anticancer agent and a modulator of multidrug-resistant tumor cells

Journal of Natural Products

Volumn 65, Issue 12, 2002, Pages 1786-1792

  Zhang, Shujun ^a   Wang, Jinlan ^a   Hirose, Katutoshi ^b   Ando, Masayoshi ^a  

^a NIIGATA UNIVERSITY   (Japan)

^b Kobe Natural Products and Chemicals Co Ltd   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; HYDROXYL GROUP; MANGANESE DIOXIDE; TAXININE; TAXININE NN 1; UNCLASSIFIED DRUG;

ACETYLATION; ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOASSAY; DRUG SYNTHESIS; IN VITRO STUDY; OXIDATION; TUMOR CELL;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; DITERPENES; DRUG RESISTANCE, NEOPLASM; DRUG SYNERGISM; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PACLITAXEL; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TAXOIDS; TUMOR CELLS, CULTURED;

EID: 1442289992     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np020240n     Document Type: Article

References (28)

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2. A preliminary report of taxinine NN 1 (1) has been reported by us. Ando, M.; Sakai, J.; Watanabe, Y.; Zhang, S.; Kosugi, K.; Suzuki, T.; Hagiwara, H. 72nd Annual Meeting of the Chemical Society of Japan, Tokyo, March, 1997, Abstract 1G3 48, p 997.
3. Ando, M. Japan Kokai Tokkyo Koho JP 10251203 A2 (September 22, 1998). Japan Patent Application JP 1997-74454 (March 10, 1997). Chem. Abstr. 1999, 129, 287930. In this patent taxinine NN-1 is called 13-acetoxy-2-hydroxytaxinine.
4. Taxinine NN-1 was also reported as Taxezopidine G. Wang, X.; Shigemori, H.; Kobayashi, J. J. Nat. Prod. 1998, 61, 474-479. Shi, Q.; Oritani, T.; Sugiyama, T.; Yamada, T. Nat. Prod. Lett. 1999, 13, 179-186.
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7. The bioassay of the modulator of multidrug-resistant cancer cells was done by the Screening Committee of New Anticancer Agent by a Grant-in-Aid for Scientific Research on Priority Area "Cancer" from the Ministry of Education, Science, Sports and Culture, Japan. We thank professor Turuo and co-workers of this committee for the bioassay of 1.
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22. 10e Their values of VCR accumulation with 1 were 419% of control and 147% of verapamil at 1 μg/mL and smaller than the values reported by us probably because of the purity of their sample.
23. Boyd, M. R.; Paull, K. D. Drug Dev. Res. 1995, 34, 91-109.
24. Yamori, T. Jpn. J. Cancer Chemother. 1997, 24, 129-135.
25. The primary screen in vitro, which consists of 39 human cancer cell lines, was done by the Screening Committee of New Anticancer Agent by a Grant-in-Aid for Scientific Research on Priority Area "Cancer" from the Ministry of Education, Science, Sports and Culture, Japan. We thank Dr. Yamori and co-workers of this committee for the bioassay of 1.
26. 12,13 Effective concentration is high enough and differential growth is recognized. Since the results of COMPARE of 1 are negative, 1 is suggested to be a new type of anticancer agent.
27. 1H NMR spectrum of 11 showed that the configurations of 13β- and 5α-hydroxyl groups were equatorial (dd, J = 9.5 and 3.5 Hz) and axial (br t, J = 2.5 Hz), respectively. The 5α(ax)-hydroxyl group is more hindered than the 13β(eq)-hydroxyl group.
28. 2O.