FR-901465
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| Category | Antibiotics |
| Catalog number | BBF-05707 |
| CAS | 146478-73-1 |
| Molecular Weight | 523.6 |
| Molecular Formula | C27H41NO9 |
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Description
FR-901465 is a potent cell cycle inhibitor isolated from Pseudomonas sp. No.2663. It exhibits potent antitumor activities against tumor cell lines via binding to the spliceosome and modulating pre-mRNA splicing.
Specification
| Synonyms | FR 901465; FR901465; WB 2663C |
| Storage | -20°C |
| IUPAC Name | [(Z,2S)-5-[[(2R,3R,5S,6S)-2,5-dimethyl-6-[(2E,4E)-3-methyl-5-[(3S,4R,5R,7R,8R)-4,5,8-trihydroxy-5-methyl-1,6-dioxaspiro[2.5]octan-7-yl]penta-2,4-dienyl]oxan-3-yl]amino]-5-oxopent-3-en-2-yl] acetate |
| Canonical SMILES | CC1CC(C(OC1CC=C(C)C=CC2C(C3(CO3)C(C(O2)(C)O)O)O)C)NC(=O)C=CC(C)OC(=O)C |
| InChI | InChI=1S/C27H41NO9/c1-15(8-11-22-24(31)27(14-34-27)25(32)26(6,33)37-22)7-10-21-16(2)13-20(18(4)36-21)28-23(30)12-9-17(3)35-19(5)29/h7-9,11-12,16-18,20-22,24-25,31-33H,10,13-14H2,1-6H3,(H,28,30)/b11-8+,12-9-,15-7+/t16-,17-,18+,20+,21-,22+,24+,25-,26+,27-/m0/s1 |
| InChI Key | DQTXAXNYLWRTPB-JIIHKXJQSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Melting Point | 86-91°C |
Reference Reading
1. New antitumor substances, FR901463, FR901464 and FR901465. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activities
H Nakajima, B Sato, T Fujita, S Takase, H Terano, M Okuhara J Antibiot (Tokyo). 1996 Dec;49(12):1196-203. doi: 10.7164/antibiotics.49.1196.
New antitumor substances, FR901463, FR901464 and FR901465 were isolated from the culture broth of a bacterium of Pseudomonas sp. No.2663. FR901463, FR901464 and FR901465 remarkably enhanced the transcriptional activity of the promoter of SV40 DNA virus. Further, these compounds exhibited potent antitumor activities against murine and human tumor cell lines in vitro.
2. New antitumor substances, FR901463, FR901464 and FR901465. II. Activities against experimental tumors in mice and mechanism of action
H Nakajima, Y Hori, H Terano, M Okuhara, T Manda, S Matsumoto, K Shimomura J Antibiot (Tokyo). 1996 Dec;49(12):1204-11. doi: 10.7164/antibiotics.49.1204.
FR901463, FR901464 and FR901465, novel antitumor substances, were isolated from the fermentation broth of Pseudomonas sp. No. 2663. Their antitumor activities were examined in three mouse tumor systems and one human tumor system. The three FR compounds prolonged the life of mice bearing murine ascitic tumor P388 leukemia (T/C values were 160%, 145% and 127% for FR901463, FR901464 and FR901465, respectively), and inhibited the growth of a human solid tumor, A549 lung adenocarcinoma, with different effective dose ranges. FR901464 exhibited most prominent effects on these tumor systems among the three FR compounds. FR901464 also inhibited the growth of murine solid tumors, Colon 38 carcinoma and Meth A fibrosarcoma. To address the involvement of transcriptional activation ability of the three FR compounds in the antitumor effect, we selected FR901464 as a candidate compound and investigated cell cycle transition, chromatin status and endogenous gene expression in FR901464-treated tumor cells having elevated transcriptional activity. FR901464 induced 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. In contrast to the potent activation of the viral promoter, FR901464 suppressed the transcription of some inducible endogenous genes but not house keeping genes in M-8 cells. These results suggest that FR901464 may induce a dynamic change of chromatin structure, giving rise to strong antitumor activity, and therefore may represent a new type of drug for cancer chemotherapy.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
