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MedKoo Cat#: 413437 | Name: Cytostatin

Description:

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

Cytostatin is an inhibitor of cell adhesion isolated from Streptomyces. Cytostatin, which is isolated from a microbial cultured broth as a low molecular weight inhibitor of cell adhesion to extracellular matrix (ECM), has anti-metastatic activity against B16 melanoma cells in vivo.

Chemical Structure

Cytostatin
Cytostatin
CAS#156856-30-3

Theoretical Analysis

MedKoo Cat#: 413437

Name: Cytostatin

CAS#: 156856-30-3

Chemical Formula: C21H33O7P

Exact Mass: 428.1964

Molecular Weight: 428.46

Elemental Analysis: C, 58.87; H, 7.76; O, 26.14; P, 7.23

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Cytostatin
IUPAC/Chemical Name
5,6-Dihydro-6-(6-hydroxy-1,5-dimethyl-4-(phosphonooxy)-7,9,11-tridecatrienyl)-5-methyl-2H-pyran-2-one
InChi Key
PQNNIEWMPIULRS-SUTYWZMXSA-N
InChi Code
InChI=1S/C21H33O7P/c1-5-6-7-8-9-10-18(22)17(4)19(28-29(24,25)26)13-11-15(2)21-16(3)12-14-20(23)27-21/h5-10,12,14-19,21-22H,11,13H2,1-4H3,(H2,24,25,26)/b6-5+,8-7+,10-9+
SMILES Code
O=C1C=CC(C)C(C(C)CCC(OP(O)(O)=O)C(C)C(O)/C=C/C=C/C=C/C)O1
Appearance
Solid powder
Purity
>98% (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
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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
Solvent mg/mL mM
Solubility
Soluble in DMSO 0.0 100.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 428.46 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.

Recalculate based on batch purity %
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
1: Kawada M, Amemiya M, Ishizuka M, Takeuchi T. Cytostatin, an inhibitor of cell adhesion to extracellular matrix, selectively inhibits protein phosphatase 2A. Biochim Biophys Acta. 1999 Nov 11;1452(2):209-17. doi: 10.1016/s0167-4889(99)00126-3. PMID: 10559474. 2: Amemiya M, Ueno M, Osono M, Masuda T, Kinoshita N, Nishida C, Hamada M, Ishizuka M, Takeuchi T. Cytostatin, a novel inhibitor of cell adhesion to components of extracellular matrix produced by Streptomyces sp. MJ654-NF4. I. Taxonomy, fermentation, isolation and biological activities. J Antibiot (Tokyo). 1994 May;47(5):536-40. doi: 10.7164/antibiotics.47.536. PMID: 8040050. 3: Lawhorn BG, Boga SB, Wolkenberg SE, Colby DA, Gauss CM, Swingle MR, Amable L, Honkanen RE, Boger DL. Total synthesis and evaluation of cytostatin, its C10-C11 diastereomers, and additional key analogues: impact on PP2A inhibition. J Am Chem Soc. 2006 Dec 27;128(51):16720-32. doi: 10.1021/ja066477d. PMID: 17177422; PMCID: PMC2566737. 4: Amemiya M, Someno T, Sawa R, Naganawa H, Ishizuka M, Takeuchi T. Cytostatin, a novel inhibitor of cell adhesion to components of extracellular matrix produced by Streptomyces sp. MJ654-NF4. II. Physico-chemical properties and structure determination. J Antibiot (Tokyo). 1994 May;47(5):541-4. doi: 10.7164/antibiotics.47.541. Erratum in: J Antibiot (Tokyo) 1994 Jul;47(7):C-14. PMID: 8040051. 5: Bialy L, Waldmann H. Total synthesis and biological evaluation of the protein phosphatase 2A inhibitor cytostatin and analogues. Chemistry. 2004 Jun 7;10(11):2759-80. doi: 10.1002/chem.200305543. PMID: 15195307. 6: Kawada M, Amemiya M, Ishizuka M, Takeuchi T. Differential induction of apoptosis in B16 melanoma and EL-4 lymphoma cells by cytostatin and bactobolin. Jpn J Cancer Res. 1999 Feb;90(2):219-25. doi: 10.1111/j.1349-7006.1999.tb00736.x. PMID: 10189893; PMCID: PMC5926052. 7: Swingle MR, Amable L, Lawhorn BG, Buck SB, Burke CP, Ratti P, Fischer KL, Boger DL, Honkanen RE. Structure-activity relationship studies of fostriecin, cytostatin, and key analogs, with PP1, PP2A, PP5, and( beta12-beta13)-chimeras (PP1/PP2A and PP5/PP2A), provide further insight into the inhibitory actions of fostriecin family inhibitors. J Pharmacol Exp Ther. 2009 Oct;331(1):45-53. doi: 10.1124/jpet.109.155630. Epub 2009 Jul 10. PMID: 19592665; PMCID: PMC2766224. 8: Yamazaki K, Amemiya M, Ishizuka M, Takeuchi T. Screening for apoptosis inducers in microbial products and induction of apoptosis by cytostatin. J Antibiot (Tokyo). 1995 Oct;48(10):1138-40. doi: 10.7164/antibiotics.48.1138. PMID: 7490221. 9: Bialy L, Waldmann H. Synthesis of the protein phosphatase 2A inhibitor (4S,5S,6S,10S,11S,12S)-cytostatin. Angew Chem Int Ed Engl. 2002 May 17;41(10):1748-51. doi: 10.1002/1521-3773(20020517)41:10<1748::aid- anie1748>3.0.co;2-x. PMID: 19750704. 10: Masuda T, Watanabe S, Amemiya M, Ishizuka M, Takeuchi T. Inhibitory effect of cytostatin on spontaneous lung metastases of B16-BL6 melanoma cells. J Antibiot (Tokyo). 1995 Jun;48(6):528-9. doi: 10.7164/antibiotics.48.528. PMID: 7622443.

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