FR901464

• CAT Number: M019956
• CAS Number: 146478-72-0
• Molecular Formula: C27H41NO8
• Molecular Weight: 507.62
• Purity: ≥95%
• Synonyms: FR901464;WB 2663B
• Target: Disease Research Fields
• Storage: -20°C
• IUPAC Name: [(Z,2S)-5-[[(2R,3R,5S,6S)-6-[(2E,4E)-5-[(3R,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
• InChI: InChI=1S/C27H41NO8/c1-16(8-11-23-25(31)27(15-33-27)14-26(6,32)36-23)7-10-22-17(2)13-21(19(4)35-22)28-24(30)12-9-18(3)34-20(5)29/h7-9,11-12,17-19,21-23,25,31-32H,10,13-15H2,1-6H3,(H,28,30)/b11-8+,12-9-,16-7+/t17-,18-,19+,21+,22-,23+,25+,26-,27+/m0/s1
• InChIKey: PJKVJJDQXZARCA-QHYZBLTGSA-N
• SMILES: CC1CC(C(OC1CC=C(C)C=CC2C(C3(CC(O2)(C)O)CO3)O)C)NC(=O)C=CC(C)OC(=O)C

FR901464（Cat No.:M019956） is a natural compound initially isolated from the bacterium Pseudomonas sp. No. 2663. It exhibits potent anticancer properties by selectively inhibiting splicing factor 3b, a critical component of the spliceosome involved in pre-mRNA splicing. This disruption affects RNA processing, leading to selective cytotoxicity in tumor cells. Due to its unique mechanism of action, FR901464 has been the subject of intense research for developing new cancer therapies. Its derivatives, like spliceostatin A, further explore its potential in clinical settings, targeting various cancers with specific genetic and molecular profiles.

Reference

1: Ghosh AK, Chen ZH, Effenberger KA, Jurica MS. 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. doi: 10.1021/jo500800k.
Epub 2014 May 30. PubMed PMID: 24873648; PubMed Central PMCID: PMC4066912.

2: He HY, Tang MC, Zhang F, Tang GL. Cis-Double bond formation by thioesterase
and transfer by ketosynthase in FR901464 biosynthesis. J Am Chem Soc. 2014 Mar
26;136(12):4488-91. doi: 10.1021/ja500942y. Epub 2014 Mar 18. PubMed PMID:
24617828.

3: Ghosh AK, Chen ZH. Enantioselective syntheses of FR901464 and spliceostatin A:
potent inhibitors of spliceosome. Org Lett. 2013 Oct 4;15(19):5088-91. doi:
10.1021/ol4024634. Epub 2013 Sep 19. PubMed PMID: 24050251; PubMed Central PMCID:
PMC3827971.

4: Liu X, Biswas S, Tang GL, Cheng YQ. Isolation and characterization of
spliceostatin B, a new analogue of FR901464, from Pseudomonas sp. No. 2663. J
Antibiot (Tokyo). 2013 Sep;66(9):555-8. doi: 10.1038/ja.2013.38. Epub 2013 May 8.
PubMed PMID: 23652603; PubMed Central PMCID: PMC4067007.

5: Fan L, Lagisetti C, Edwards CC, Webb TR, Potter PM. Sudemycins, novel small
molecule analogues of FR901464, induce alternative gene splicing. ACS Chem Biol.
2011 Jun 17;6(6):582-9. doi: 10.1021/cb100356k. Epub 2011 Mar 7. PubMed PMID:
21344922; PubMed Central PMCID: PMC3113647.

6: Zhang F, He HY, Tang MC, Tang YM, Zhou Q, Tang GL. Cloning and elucidation of
the FR901464 gene cluster revealing a complex acyltransferase-less polyketide
synthase using glycerate as starter units. J Am Chem Soc. 2011 Mar
2;133(8):2452-62. doi: 10.1021/ja105649g. Epub 2011 Feb 3. PubMed PMID: 21291275.

7: Osman S, Albert BJ, Wang Y, Li M, Czaicki NL, Koide K. Structural requirements
for the antiproliferative activity of pre-mRNA splicing inhibitor FR901464.
Chemistry. 2011 Jan 17;17(3):895-904. doi: 10.1002/chem.201002402. Epub 2010 Nov
19. PubMed PMID: 21226105; PubMed Central PMCID: PMC3529175.