Inostamycin A | CAS#129905-10-8 | Anticancer bacterial metabolite

MedKoo Cat#: 464414 | Name: Inostamycin A

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Inostamycin A

CAS#129905-10-8

Theoretical Analysis

MedKoo Cat#: 464414

Name: Inostamycin A

CAS#: 129905-10-8

Chemical Formula: C38H68O11

Exact Mass: 700.4762

Molecular Weight: 700.95

Elemental Analysis: C, 65.11; H, 9.78; O, 25.11

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 1,050.00	2 Weeks

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Related CAS #

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Synonym

Inostamycin A; Inostamycin-A; Inostamycin;

IUPAC/Chemical Name

(R)-2-((2R,3S,4R,5S,6R)-5-ethyl-6-((2S,3S,4S,6R)-6-((2S,2'R,3'R,4S,5S,5'R)-5'-ethyl-2'-hydroxy-5'-((S)-1-hydroxybutyl)-2,3',4-trimethyloctahydro-[2,2'-bifuran]-5-yl)-3-hydroxy-4-methyl-5-oxooctan-2-yl)-2,4-dihydroxy-3-methyltetrahydro-2H-pyran-2-yl)butanoic acid

InChi Key

NZJHONRWXITMMC-LPMSCSBASA-N

InChi Code

InChI=1S/C38H68O11/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)/t20-,21+,22-,23-,24-,25-,26-,27-,28-,29+,31-,32-,33+,35-,36+,37+,38+/m0/s1

SMILES Code

O[C@]1([C@@](C[C@@H]2C)(C)O[C@@]2([C@H](C([C@H]([C@H]([C@H](C)[C@]([H])([C@@H](CC)[C@@H](O)[C@@H]3C)O[C@]3([C@H](C(O)=O)CC)O)O)C)=O)CC)[H])[C@H](C)C[C@](CC)([C@H](CCC)O)O1

Appearance

Solid powder

Purity

>90% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Inostamycin A is a bacterial metabolite that has been found in Streptomyces and has anticancer activity.

In vitro activity:

Treatment of exponentially proliferating Ms-1 cells with low concentrations of inostamycin caused cells to accumulate in the G1 phase. This study found that inostamycin decreased cyclin D1, and increased cyclin-dependent kinase inhibitors such as p21WAF1 and p27KIP1 in Ms-1 cells. Reference: Jpn J Cancer Res. 1998 Mar;89(3):315-22. https://pubmed.ncbi.nlm.nih.gov/9600126/

In vivo activity:

TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 700.95 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Imoto M, Tanabe K, Simizu S, Tashiro E, Takada M, Umezawa K. Inhibition of cyclin D1 expression and induction of apoptosis by inostamycin in small cell lung carcinoma cells. Jpn J Cancer Res. 1998 Mar;89(3):315-22. doi: 10.1111/j.1349-7006.1998.tb00564.x. PMID: 9600126; PMCID: PMC5921804. 2. Deguchi A, Imoto M, Umezawa K. Inhibition of G1 cyclin expression in normal rat kidney cells by inostamycin, a phosphatidylinositol synthesis inhibitor. J Biochem. 1996 Dec;120(6):1118-22. doi: 10.1093/oxfordjournals.jbchem.a021530. PMID: 9010759.

In vitro protocol:

In vivo protocol:

TBD

1: Yu G, Jung B, Lee HS, Kang SH. The Total Synthesis of Inostamycin A. Angew Chem Int Ed Engl. 2016 Feb 12;55(7):2573-6. doi: 10.1002/anie.201510852. Epub 2016 Jan 22. PMID: 26800259. 2: Yamamoto K, Makino M, Watanapokasin R, Tashiro E, Imoto M. Inostamycin enhanced TRAIL-induced apoptosis through DR5 upregulation on the cell surface. J Antibiot (Tokyo). 2012 Jun;65(6):295-300. doi: 10.1038/ja.2012.21. Epub 2012 Apr 4. PMID: 22472572. 3: Baba Y, Kato Y, Ogawa K. Inostamycin prevents malignant phenotype of cancer: inhibition of phosphatidylinositol synthesis provides a therapeutic advantage for head and neck squamous cell carcinoma. Cell Biol Int. 2010 Feb;34(2):171-5. doi: 10.1042/CBI20090310. PMID: 20070255. 4: Fang J, Nakamura H, Iyer AK. Tumor-targeted induction of oxystress for cancer therapy. J Drug Target. 2007 Aug-Sep;15(7-8):475-86. doi: 10.1080/10611860701498286. PMID: 17671894. 5: Fuller NO, Morken JP. Studies on the synthesis of the inostamycin natural products: a reductive aldol/reductive Claisen approach to the C10-C24 ketone fragment. Org Lett. 2005 Oct 27;7(22):4867-9. doi: 10.1021/ol0516115. PMID: 16235909. 6: Baba Y, Kato Y, Mochimatsu I, Nagashima Y, Kurihara M, Kawano T, Taguchi T, Hata R, Tsukuda M. Inostamycin suppresses vascular endothelial growth factor- stimulated growth and migration of human umbilical vein endothelial cells. Clin Exp Metastasis. 2004;21(5):419-25. doi: 10.1007/s10585-005-0041-0. PMID: 15672866. 7: Kawatani M, Uchi M, Simizu S, Osada H, Imoto M. Transmembrane domain of Bcl-2 is required for inhibition of ceramide synthesis, but not cytochrome c release in the pathway of inostamycin-induced apoptosis. Exp Cell Res. 2003 May 15;286(1):57-66. doi: 10.1016/s0014-4827(03)00098-3. PMID: 12729794. 8: Baba Y, Tsukuda M, Mochimatsu I, Furukawa S, Kagata H, Nagashima Y, Koshika S, Imoto M, Kato Y. 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. 2001;25(7):613-20. doi: 10.1006/cbir.2000.0706. PMID: 11448100. 9: Imoto M. [Study of the novel compounds modulating signal transduction system from microbial origin]. Jpn J Antibiot. 2001 Mar;54(3):117-25. Japanese. PMID: 11392682. 10: Baba Y, Tsukuda M, Mochimatsu I, Furukawa S, Kagata H, Yoji, Nagashima, Sakai N, Koshika S, Imoto M, Kato Y. 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. 2000;18(3):273-9. doi: 10.1023/a:1006798900743. PMID: 11315101. 11: Kawatani M, Simizu S, Osada H, Takada M, Arber N, Imoto M. Involvement of protein kinase C-regulated ceramide generation in inostamycin-induced apoptosis. Exp Cell Res. 2000 Sep 15;259(2):389-97. doi: 10.1006/excr.2000.4986. PMID: 10964506. 12: Simizu S, Tanabe K, Tashiro E, Takada M, Umezawa K, Imoto M. Potentiation of paclitaxel cytotoxicity by inostamycin in human small cell lung carcinoma, Ms-1 cells. Jpn J Cancer Res. 1998 Sep;89(9):970-6. doi: 10.1111/j.1349-7006.1998.tb00656.x. PMID: 9818034; PMCID: PMC5921940. 13: Simizu S, Takada M, Umezawa K, Imoto M. Requirement of caspase-3(-like) protease-mediated hydrogen peroxide production for apoptosis induced by various anticancer drugs. J Biol Chem. 1998 Oct 9;273(41):26900-7. doi: 10.1074/jbc.273.41.26900. PMID: 9756937. 14: Imoto M, Tanabe K, Simizu S, Tashiro E, Takada M, Umezawa K. Inhibition of cyclin D1 expression and induction of apoptosis by inostamycin in small cell lung carcinoma cells. Jpn J Cancer Res. 1998 Mar;89(3):315-22. doi: 10.1111/j.1349-7006.1998.tb00564.x. PMID: 9600126; PMCID: PMC5921804. 15: Umezawa K, Deguchi A, Imoto M. [Screening of phosphatidylinositol turnover inhibitors and regulation of cell cycle progression]. Gan To Kagaku Ryoho. 1997 Sep;24(11):1578-84. Japanese. PMID: 9309157. 16: Deguchi A, Imoto M, Umezawa K. Inhibition of G1 cyclin expression in normal rat kidney cells by inostamycin, a phosphatidylinositol synthesis inhibitor. J Biochem. 1996 Dec;120(6):1118-22. doi: 10.1093/oxfordjournals.jbchem.a021530. PMID: 9010759. 17: Kawada M, Umezawa K. Inostamycin, an inhibitor of P-glycoprotein function, interacts specifically with phosphatidylethanolamine. Jpn J Cancer Res. 1995 Sep;86(9):873-8. doi: 10.1111/j.1349-7006.1995.tb03099.x. PMID: 7591966; PMCID: PMC5920936. 18: Umezawa K. Isolation and biological activities of signal transduction inhibitors from microorganisms and plants. Adv Enzyme Regul. 1995;35:43-53. doi: 10.1016/0065-2571(94)00018-x. PMID: 7572353. 19: Imoto M, Morii T, Deguchi A, Umezawa K. Involvement of phosphatidylinositol synthesis in the regulation of S phase induction. Exp Cell Res. 1994 Nov;215(1):228-33. doi: 10.1006/excr.1994.1336. PMID: 7957673. 20: Odai H, Shindo K, Odagawa A, Mochizuki J, Hamada M, Takeuchi T. Inostamycins B and C, new polyether antibiotics. J Antibiot (Tokyo). 1994 Aug;47(8):939-41. doi: 10.7164/antibiotics.47.939. PMID: 7928682.