FR901464

Names

[ Name ]:
FR901464

[Synonym ]:
WB 2663B
[(E,2S)-5-[[(2R,5S,6S)-6-[(2E,4E)-5-[(4R,5R,7S)-4,7-dihydroxy-7-methyl-1,6-dioxaspiro[2.5]octan-5-yl]-3-methylpenta-2,4-dienyl]-2,5-dimethyloxan-3-yl]amino]-5-oxopent-3-en-2-yl] acetate
[(E,2S)-5-[[(2R,5S,6S)-6-[(2E,4E)-5-[(5S,7R,8R)-5,8-dihydroxy-5-methyl-2,6-dioxaspiro[2.5]octan-7-yl]-3-methylpenta-2,4-dienyl]-2,5-dimethyloxan-3-yl]amino]-5-oxopent-3-en-2-yl] acetate

Biological Activity

[Description]:

FR901464 is a potent spliceosome inhibitor with prominent anti-tumor and anti-cancer effects[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Others >> Others

[In Vitro]

FR901464 (10-20 ng/ml; 6-24 hours) inhibits the growth of murine solid tumors, Colon 38 carcinoma and Meth A fibrosarcoma. FR901464 induces characteristic G1 and G2/M phase arrest in the cell cycle and internucleosomal degradation of genomic DNA with the same kinetics as activation of SV40 promoter-dependent cellular transcription in M-8 tumor cells[1]. FR901464 (1-10 ng/ml; 16 hours) suppresses the transcription of some inducible endogenous genes but not house keeping genes in M-8 cells[1]. FR901464 exhibits potent anticancer activity. It shows enhancement of activity of a promoter of the SV40 DNA tumor virus at 10 nM concentration in M-8 cells[1].

[References]

[1]. H Nakajima, et al. New antitumor substances, FR901463, FR901464 and FR901465. II. Activities against experimental tumors in mice and mechanism of action. J Antibiot (Tokyo). 1996 Dec;49(12):1204-11.

[2]. Arun K Ghosh, et al. Enantioselective total syntheses of FR901464 and spliceostatin A and evaluation of splicing activity of key derivatives. J Org Chem. 2014 Jun 20;79(12):5697-709.

Chemical & Physical Properties

[ Density]:
1.21g/cm3

[ Boiling Point ]:
702.7ºC at 760mmHg

[ Molecular Formula ]:
C₂₇H₄₁NO₈

[ Molecular Weight ]:
507.61600

[ Flash Point ]:
378.8ºC

[ Exact Mass ]:
507.28300

[ PSA ]:
130.34000

[ LogP ]:
3.15270

[ Vapour Pressure ]:
7.94E-23mmHg at 25°C

[ Index of Refraction ]:
1.553

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: ZC0702750

CHEMICAL NAME :: WB 2663B

CAS REGISTRY NUMBER :: 146478-72-0

LAST UPDATED :: 199806

DATA ITEMS CITED :: 1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3200 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 49,1196,1996

Safety Information

[ Hazard Codes ]:
Xi

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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