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Inhibitor of Phosphatidylinositol Turnover Inostamycin A (sodium salt)

Date：July 03 2020Web Page No：520050

Institute of Microbial Chemistry

Inostamycin A is isolated from the culture fluid of Streptomyces sp. MH816-AF15 and inhibits cytidine diphosphodiacylglycerol (CDP-DG): inositol transferase 1). Inostamycin A inhibited the incorporation of inositol into inositol lipids induced by EGF in an assay system using A431 cells, with 50 an IC50 value of approximately 0.5 μg/ml 2). The IC50 of in vitro CDP-DG in A431 cell membranes was approximately 0.02 μg/ml 1). It exhibited cytolytic activity against srk-NIH-3T3 cells (IC50: approximately 0.07 μg/ml) 3). Inostamycin A at 3 μg/ml enhanced the cytotoxicity of colchicine against KB-C4 cells 4). 0.1 μg/ml caused accumulation of MS-1 cells into the G1 phase, while a higher concentration (0.3 μg/ml) induced morphological apoptosis 6). It has also been reported that it enhances the cell-killing effect of taxol against small cell lung cancer cells 5).

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Inostamycin A Structure

Specification

CAS#1884611-95-3
Molecular FormulaC38H67O11 Na
Molecular Weight722.933
SourceStreptomyces sp. MH816-AF15
Purity> 90% (Quantitative NMR)
SolubilitySoluble in DMSO, DMF and CHCl3. Poorly soluble in H2O
* This product is supplied as a sodium salt form.

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Mechanism

Inostamycin A Mechanism

Phosphatidylinositol 2-phosphate (PIP2), generated from phosphatidylinositol (PI) present in the cell membrane, is degraded by phospholipase C (PLC) to inositol triphosphate (IP3) and diacylglycerol (DG), and IP3 is converted to inositol (I). The inositol (I) is bound to CDP-DG and PI is resynthesized. This metabolic turnover is called the inositol phospholipid turnover. IP3 generated by this turnover releases Ca2+ from the endoplasmic reticulum, and the Ca2+ and DG activate protein kinase C (PKC), which phosphorylates various intracellular proteins to activate proliferation signals and cancer malignancy signals.
Inostamycin A inhibits the synthesis of PI from I and CDP-DG in inositol-phospholipid-turnover and arrests cell-cycle in G1 phase, thereby inhibiting cell proliferation 2).

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Application Note

  • Inhibited in vitro CDP-DG: inositol transferase activity of the A431 cell membrane, the IC50 was about 0.02 μg/ml 1)
  • Inhibited EGF-induced inositol incorporation into inositol lipids with an IC50 of about 0.5 μg/ml in the A431 cell assay system 2)
  • Showed antimicrobial activities against Gram-positive bacteria and cytocidal activity against srk-NIH-3T3 cell with IC50 value of 0.07 μg/ml 3)
  • Potenciated colchitine cytotoxicity toward KB-C4 cells at 3 μg/ml 4)
  • Enhanced the cytotoxic effect of Taxol on small cell lung cancer cells 5)
  • Caused Ms-1 cell to accumulate in the G1 phase at 0.1 μg/ml and induces morphological apoptosis at high concentration (0.3 μg/ml) 6)
  • It irreversibly binds to the cell membrane of multidrug-resistant human cancer cell line KB, and irreversibly inhibits P-glycoprotein through specific interaction with phospholipid phosphatidylethanolamine 7).
  • When the concentration of inostamycin in the culture medium was 62.5~125 ng/ml, cell proliferation of the human oral squamous cell carcinoma cell line used in the study was inhibited 8).

* Biological activity of the product was not verified. The values shown above were cited from the references.


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Reference

  1. Imoto M., et al., J. Biochem., 112, 299-302(1992). [PMID:1328172]
  2. Imoto M., et al., J. Nat. Prod., 53(4), 825-829(1990). [DOI:10.1021/np50070a008]
  3. Odai H., et al., J. Antibiot., 47(8), 939-941(1994). [PMID:7928682]
  4. Kawada M., et al., J. Antibiot., 45(4), 556-562(1992). [PMID:1592687]
  5. Imoto M., et al., Jpn. J. Cancer Res., 89(3), 315-322(1998). [PMID:9600126]
  6. Simizu S., et al., Jpn. J. Cancer Res., 89(9), 970-976(1998). [PMID:9818034]
  7. Kawada, M. and Umezawa, K., Jpn. J. Cancer Res., 86(9), 873-878(1995). [PMID:7591966]
  8. Baba, Y., et al., Cell Biol. Int., 25(7), 613-620(2001). [PMID:11448100]

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[Date : May 17 2026 00:07]

Detail Product Name Product Code Supplier Size Price
Inostamycin A (Sodium Salt), Antitumor
DatasheetThis may not be the latest data sheet. 		14652 IMCInstitute of Microbial Chemistry 1 mg $500

Description M.W.: 722.933 (Sodium salt) Purity : >90% (qNMR) Molecular Formula : C38H68O11Na (Sodium salt) Solubility : Soluble in DMSO, DMF, and CHCl3, Poorly soluble in H2O. Inostamycin A is an inhibitor of phosphatidylinositol turnover, supplied as sodium salt. It was reported that this compound inhibited EGF-induced inositol incorporation into inositol lipids in the A431 cell assay system. It was also reported that inhibition of in vitro CDP-DG: inositol transferase activity of the A431 cell membrane, antimicrobial activities against gram-positive bacteria, cytocidal activity against srk-NIH-3T3, and potentiated colchicine cytotoxicity toward KB-C4 cells. In addition, it caused Ms-1 cell to accumulate in the G1 phase and induced morphological apoptosis at high concentration.
Storage -20°C CAS 1884611-95-3 (sodium salt), 129905-10-8 (salt free form)
Link

Bioactive Compounds

[Date : May 17 2026 00:07]

Inostamycin A (Sodium Salt), Antitumor

DatasheetThis may not be the latest data sheet.


  • Product Code: 14652
  • Supplier: IMC
  • Size: 1mg
  • Price: $500

Description M.W.: 722.933 (Sodium salt) Purity : >90% (qNMR) Molecular Formula : C38H68O11Na (Sodium salt) Solubility : Soluble in DMSO, DMF, and CHCl3, Poorly soluble in H2O. Inostamycin A is an inhibitor of phosphatidylinositol turnover, supplied as sodium salt. It was reported that this compound inhibited EGF-induced inositol incorporation into inositol lipids in the A431 cell assay system. It was also reported that inhibition of in vitro CDP-DG: inositol transferase activity of the A431 cell membrane, antimicrobial activities against gram-positive bacteria, cytocidal activity against srk-NIH-3T3, and potentiated colchicine cytotoxicity toward KB-C4 cells. In addition, it caused Ms-1 cell to accumulate in the G1 phase and induced morphological apoptosis at high concentration.
Storage -20°C CAS 1884611-95-3 (sodium salt), 129905-10-8 (salt free form)
Link

Bioactive Compounds

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