Inostamycin A (sodium salt)

Inostamycin A is a bacterial metabolite that has been found in Streptomyces and has anticancer activity. 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. 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. 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. Inostamycin A also reduces levels of matrix metalloproteinase-2 (MMP-2) and MMP-9 and inhibits EGF-induced migration of HSC-4 cells.Formal Name: (alphaR,2R,3S,4R,5S,6R)-alpha,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: (Request formulation change), A solid. Solubility: Acetone: soluble, Chloroform: soluble, Methanol: 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..