Cysmethynil
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MedKoo CAT#: 406303

CAS#: 851636-83-4

Description: Cysmethynil is a potent inhibitor of isoprenylcysteine carboxyl methyltransferase (ICMT) with antitumor activity in cancer cells. Cysmethynil treatment results in inhibition of cell growth in an Icmt-dependent fashion, demonstrating mechanism-based activity of the compound. Treatment of cancer cells with cysmethynil results in mislocalization of Ras and impaired epidermal growth factor signaling. In a human colon cancer cell line, cysmethynil treatment blocks anchorage-independent growth, and this effect is reversed by overexpression of Icmt.


Chemical Structure

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Cysmethynil
CAS# 851636-83-4

Theoretical Analysis

MedKoo Cat#: 406303
Name: Cysmethynil
CAS#: 851636-83-4
Chemical Formula: C25H32N2O
Exact Mass: 376.25146
Molecular Weight: 376.53438
Elemental Analysis: C, 79.75; H, 8.57; N, 7.44; O, 4.25

Price and Availability

Size Price Availability Quantity
5.0mg USD 185.0 2 Weeks
10.0mg USD 350.0 2 Weeks
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Synonym: Cysmethynil

IUPAC/Chemical Name: 2-(1-octyl-5-(m-tolyl)-1H-indol-3-yl)acetamide

InChi Key: QIXBOOVPFRZHQQ-UHFFFAOYSA-N

InChi Code: InChI=1S/C25H32N2O/c1-3-4-5-6-7-8-14-27-18-22(17-25(26)28)23-16-21(12-13-24(23)27)20-11-9-10-19(2)15-20/h9-13,15-16,18H,3-8,14,17H2,1-2H3,(H2,26,28)

SMILES Code: O=C(N)CC1=CN(CCCCCCCC)C2=C1C=C(C3=CC=CC(C)=C3)C=C2

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, not in water

Shelf Life: >5 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

Certificate of Analysis:

Safety Data Sheet (SDS):

Preparing Stock Solutions

The following data is based on the product molecular weight 376.53438 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

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1: Ramanujulu PM, Yang T, Yap SQ, Wong FC, Casey PJ, Wang M, Go ML. Functionalized indoleamines as potent, drug-like inhibitors of isoprenylcysteine carboxyl methyltransferase (Icmt). Eur J Med Chem. 2013 May;63:378-86. doi: 10.1016/j.ejmech.2013.02.007. Epub 2013 Feb 21. PubMed PMID: 23514631.

2: Go ML, Leow JL, Gorla SK, Schüller AP, Wang M, Casey PJ. Amino derivatives of indole as potent inhibitors of isoprenylcysteine carboxyl methyltransferase. J Med Chem. 2010 Oct 14;53(19):6838-50. doi: 10.1021/jm1002843. PubMed PMID: 20809634.

3: Wang M, Hossain MS, Tan W, Coolman B, Zhou J, Liu S, Casey PJ. Inhibition of isoprenylcysteine carboxylmethyltransferase induces autophagic-dependent apoptosis and impairs tumor growth. Oncogene. 2010 Sep 2;29(35):4959-70. doi: 10.1038/onc.2010.247. Epub 2010 Jul 12. PubMed PMID: 20622895.

4: Cushman I, Casey PJ. Role of isoprenylcysteine carboxylmethyltransferase-catalyzed methylation in Rho function and migration. J Biol Chem. 2009 Oct 9;284(41):27964-73. doi: 10.1074/jbc.M109.025296. Epub 2009 Aug 3. PubMed PMID: 19651782; PubMed Central PMCID: PMC2788848.

5: Wang M, Khoo YM, Zhou J, Casey P, Lee HS. A high-performance liquid chromatography method for the quantification of cysmethynil, an inhibitor of isoprenylcysteine carboxylmethyl transferase, in mouse plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Feb 15;877(5-6):553-7. doi: 10.1016/j.jchromb.2008.12.067. Epub 2009 Jan 6. PubMed PMID: 19157999.

6: Wang M, Tan W, Zhou J, Leow J, Go M, Lee HS, Casey PJ. A small molecule inhibitor of isoprenylcysteine carboxymethyltransferase induces autophagic cell death in PC3 prostate cancer cells. J Biol Chem. 2008 Jul 4;283(27):18678-84. doi: 10.1074/jbc.M801855200. Epub 2008 Apr 23. PubMed PMID: 18434300.

7: Baron RA, Peterson YK, Otto JC, Rudolph J, Casey PJ. Time-dependent inhibition of isoprenylcysteine carboxyl methyltransferase by indole-based small molecules. Biochemistry. 2007 Jan 16;46(2):554-60. PubMed PMID: 17209565.

8: Leow JL, Baron R, Casey PJ, Go ML. Quantitative structure-activity relationship (QSAR) of indoloacetamides as inhibitors of human isoprenylcysteine carboxyl methyltransferase. Bioorg Med Chem Lett. 2007 Feb 15;17(4):1025-32. Epub 2006 Nov 15. PubMed PMID: 17157012; PubMed Central PMCID: PMC1941685.

9: Svensson AW, Casey PJ, Young SG, Bergo MO. Genetic and pharmacologic analyses of the role of Icmt in Ras membrane association and function. Methods Enzymol. 2006;407:144-59. PubMed PMID: 16757321.

10: Winter-Vann AM, Baron RA, Wong W, dela Cruz J, York JD, Gooden DM, Bergo MO, Young SG, Toone EJ, Casey PJ. A small-molecule inhibitor of isoprenylcysteine carboxyl methyltransferase with antitumor activity in cancer cells. Proc Natl Acad Sci U S A. 2005 Mar 22;102(12):4336-41. PubMed PMID: 15784746; PubMed Central PMCID: PMC555472.



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