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

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

MedKoo CAT#: 464414

CAS#: 129905-10-8

Description: 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

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 464414
Name: Inostamycin A
CAS#: 129905-10-8
Chemical Formula: C38H68O11
Exact Mass: 700.48
Molecular Weight: 700.951
Elemental Analysis: C, 65.11; H, 9.78; O, 25.11

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 1050	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

More Info:

Product Data:

Product Data

Instruction:

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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:	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 vivo protocol:	TBD

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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.

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Inostamycin A featured