| Identification | Back Directory | [Name]
inostamycin | [CAS]
129905-10-8 | [Synonyms]
inostamycin
Inostamycin A
(2S,4S,5R)-20-De(1-hydroxypropyl)-6-demethyl-2,6-diethyl-5-hydroxy-20-(1-hydroxybutyl)lysocellin
2H-Pyran-2-acetic acid, α,5-diethyl-6-[(1S,2S,3S,5R)-5-[(2S,2'R,3'R,4S,5S,5'R)-5'-ethyloctahydro-2'-hydroxy-5'-[(1S)-1-hydroxybutyl]-2,3',4-trimethyl[2,2'-bifuran]-5-yl]-2-hydroxy-1,3-dimethyl-4-oxoheptyl]tetrahydro-2,4-dihydroxy-3-methyl-, (αR,2R,3S,4R,5S,6R)- | [Molecular Formula]
C38H68O11 | [MDL Number]
MFCD01716164 | [MOL File]
129905-10-8.mol | [Molecular Weight]
700.94 |
| Hazard Information | Back Directory | [Biological Activity]
Inostamycin A is a bacterial metabolite that has been found in Streptomyces and has anticancer activity.1 It is an inhibitor of CDP-diacylglycerol:inositol 3-phosphatidyltransferase (IC50 = 0.02 μg/ml in A431 cell membranes) and is selective for CDP-diacylglycerol:inositol 3-phosphatidyltransferase over phospholipase C (PLC) and phosphatidylinositol kinase at 10 μg/ml.2 Inostamycin A decreases viability of YCU-T892, KCC-TC873, KB, HSC-4, and YCU-T891 oral squamous cell carcinoma (OSCC) cells in a concentration-dependent manner.3 It induces cell cycle arrest in the G1 phase in HSC-4 cells when used at a concentration of 250 ng/ml and induces apoptosis in Ms-1 small cell lung cancer cells at 300 ng/ml.3,4 Inostamycin A also reduces levels of matrix metalloproteinase-2 (MMP-2) and MMP-9 and inhibits EGF-induced migration of HSC-4 cells.5 | [storage]
-20°C | [References]
1.Imoto, M., Umezawa, K., Takahashi, Y., et al.Isolation and structure determination of inostamycin, a novel inhibitor of phosphatidylinositol turnoverJ. Nat. Prod.53(4)825-829(1990)
2.Imoto, M., Taniguchi, Y., and Umezawa, K.Inhibition of CDP-DG: inositol transferase by inostamycinJ. Biochem.112(2)299-302(1992)
3.Baba, Y., Tsukuda, M., Mochimatsu, I., et al.Cytostatic effect of inostamycin, an inhibitor of cytidine 5'-diphosphate 1,2-diacyl-sn-glycerol (CDP-DG): inositol transferase, on oral squamous cell carcinoma cell linesCell Biol. Int.25(7)613-620(2001)
4.Imoto, M., Tanabe, K., Simizu, S., et al.Inhibition of cyclin D1 expression and induction of apoptosis by inostamycin in small cell lung carcinoma cellsJpn. J. Cancer Res.89(3)315-322(1998)
5.Baba, Y., Tsukuda, M., Mochimatsu, I., et al.Inostamycin, an inhibitor of cytidine 5'-diphosphate 1,2-diacyl-sn-glycerol (CDP-DG): Inositol transferase, suppresses invasion ability by reducing productions of matrix metalloproteinase-2 and -9 and cell motility in HSC-4 tongue carcinoma cell lineClin. Exp. Metastasis18(3)273-279(2000)
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