A bacterial metabolite with anticancer activity
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Inostamycin A (sodium salt)

Item No. 33018

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(αR,2R,3S,4R,5S,6R)-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-2H-pyran-2-acetic acid, monosodium salt
Synonyms
  • Inostamycin
Molecular Formula
C38H68O11 • Na
Formula Weight
723.9
Purity
≥85%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Acetone: solubleChloroform: solubleMethanol: soluble
SMILES
O[C@@]([C@@H](C1)C)([C@@](O[C@]2([H])[C@@H](CC)C([C@@H](C)[C@@H](O)[C@@H]([C@](O[C@@]3(O)[C@@H](CC)C(O)=O)([H])[C@H]([C@H]([C@@H]3C)O)CC)C)=O)(C[C@@H]2C)C)O[C@@]1(CC)[C@@H](O)CCC.[Na+]
InChi Code
InChI=1S/C38H68O11.Na/c1-12-17-28(39)36(16-5)19-21(7)38(46,49-36)35(11)18-20(6)32(47-35)25(13-2)30(41)22(8)29(40)23(9)33-26(14-3)31(42)24(10)37(45,48-33)27(15-4)34(43)44;/h20-29,31-33,39-40,42,45-46H,12-19H2,1-11H3,(H,43,44);/q;+1/t20-,21+,22-,23-,24-,25-,26-,27-,28-,29+,31-,32-,33+,35-,36+,37+,38+;/m0./s1
InChi Key
UIRAWSBFRCUWPU-YOTSDDHGSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $788

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    Product Description

    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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Imoto, M., Umezawa, K., Takahashi, Y., et al. Isolation and structure determination of inostamycin, a novel inhibitor of phosphatidylinositol turnover. J. Nat. Prod. 53(4), 825-829 (1990).

    2. Imoto, M., Taniguchi, Y., and Umezawa, K. Inhibition of CDP-DG: inositol transferase by inostamycin. J. 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 lines. Cell 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 cells. Jpn. 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 line. Clin. Exp. Metastasis 18(3), 273-279 (2000).