Cytostatin

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MedKoo CAT#: 413437

CAS#: 156856-30-3

Description: 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

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Cytostatin
CAS# 156856-30-3
Instruction

Theoretical Analysis

MedKoo Cat#: 413437
Name: Cytostatin
CAS#: 156856-30-3
Chemical Formula: C21H33O7P
Exact Mass: 428.20
Molecular Weight: 428.460
Elemental Analysis: C, 58.87; H, 7.76; O, 26.14; P, 7.23

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Soluble in DMSO 0.0 100.00

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.