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MedKoo Cat#: 406303 | Name: Cysmethynil
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Description:

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

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

Cysmethynil
Cysmethynil
CAS#851636-83-4

Theoretical Analysis

MedKoo Cat#: 406303

Name: Cysmethynil

CAS#: 851636-83-4

Chemical Formula: C25H32N2O

Exact Mass: 376.2515

Molecular Weight: 376.53

Elemental Analysis: C, 79.75; H, 8.57; N, 7.44; O, 4.25

Price and Availability

Size Price Availability Quantity
10mg USD 400.00 2 Weeks
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Related CAS #
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Synonym
Cysmethynil; Icmt Inhibitor;
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
More Info
        
Certificate of Analysis
View CoA: current batch, Lot#C20M05C26
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 376.53 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: Yang WS, Yeo SG, Yang S, Kim KH, Yoo BC, Cho JY. Isoprenyl carboxyl methyltransferase inhibitors: a brief review including recent patents. Amino Acids. 2017 Sep;49(9):1469-1485. doi: 10.1007/s00726-017-2454-x. Epub 2017 Jun 19. PMID: 28631011; PMCID: PMC5561173. 2: 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. PMID: 19157999. 3: Sun WT, Xiang W, Ng BL, Asari K, Bunte RM, Casey PJ, Wang M, Chuah C. Inhibition of isoprenylcysteine carboxylmethyltransferase augments BCR-ABL1 tyrosine kinase inhibition-induced apoptosis in chronic myeloid leukemia. Exp Hematol. 2016 Mar;44(3):189-93.e2. doi: 10.1016/j.exphem.2015.12.002. Epub 2015 Dec 17. PMID: 26706195. 4: Magkouta S, Pappas A, Moschos C, Vazakidou ME, Psarra K, Kalomenidis I. Icmt inhibition exerts anti-angiogenic and anti-hyperpermeability activities impeding malignant pleural effusion. Oncotarget. 2016 Apr 12;7(15):20249-59. doi: 10.18632/oncotarget.7912. PMID: 26959120; PMCID: PMC4991451. 5: Arendt KAM, Ntaliarda G, Armenis V, Kati D, Henning C, Giotopoulou GA, Pepe MAA, Klotz LV, Lamort AS, Hatz RA, Kobold S, Schamberger AC, Stathopoulos GT. An In Vivo Inflammatory Loop Potentiates KRAS Blockade. Biomedicines. 2022 Mar 3;10(3):592. doi: 10.3390/biomedicines10030592. PMID: 35327394; PMCID: PMC8945202. 6: 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. PMID: 20622895. 7: Yan F, Bai JF, Dong Y, Liu S, Li C, Du CX, Li Y. Catalytic Cyanation of C-N Bonds with CO2/NH3. JACS Au. 2022 Oct 20;2(11):2522-2528. doi: 10.1021/jacsau.2c00392. PMID: 36465537; PMCID: PMC9709945. 8: Lau HY, Ramanujulu PM, Guo D, Yang T, Wirawan M, Casey PJ, Go ML, Wang M. An improved isoprenylcysteine carboxylmethyltransferase inhibitor induces cancer cell death and attenuates tumor growth in vivo. Cancer Biol Ther. 2014 Sep;15(9):1280-91. doi: 10.4161/cbt.29692. Epub 2014 Jun 27. PMID: 24971579; PMCID: PMC4128870. 9: 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. PMID: 18434300. 10: Zhu Y, Hu Q, Li H. Isoprenylcysteine carboxylmethyltransferase is associated with nasopharyngeal carcinoma chemoresistance and Ras activation. Biochem Biophys Res Commun. 2019 Aug 27;516(3):784-789. doi: 10.1016/j.bbrc.2019.06.074. Epub 2019 Jun 26. PMID: 31253403. 11: 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. doi: 10.1073/pnas.0408107102. PMID: 15784746; PMCID: PMC555472. 12: 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. PMID: 23514631. 13: Pan Q, Liu R, Banu H, Ma L, Li H. Inhibition of isoprenylcysteine carboxylmethyltransferase sensitizes common chemotherapies in cervical cancer via Ras-dependent pathway. Biomed Pharmacother. 2018 Mar;99:169-175. doi: 10.1016/j.biopha.2018.01.048. Epub 2018 Jan 11. PMID: 29331763. 14: Yang WS, Kim HG, Lee Y, Yoon K, Kim S, Kim JH, Cho JY. Isoprenylcysteine carboxyl methyltransferase inhibitors exerts anti-inflammatory activity. Biochem Pharmacol. 2020 Dec;182:114219. doi: 10.1016/j.bcp.2020.114219. Epub 2020 Sep 12. PMID: 32931773. 15: 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. doi: 10.1021/bi060344n. PMID: 17209565. 16: Liu Q, Chen J, Fu B, Dai J, Zhao Y, Lai L. Isoprenylcysteine carboxylmethyltransferase regulates ovarian cancer cell response to chemotherapy and Ras activation. Biochem Biophys Res Commun. 2018 Jun 22;501(2):556-562. doi: 10.1016/j.bbrc.2018.05.038. Epub 2018 May 11. PMID: 29746868. 17: Cushman I, Casey PJ. Role of isoprenylcysteine carboxylmethyltransferase- catalyzed methylation in Rho function and migration. J Biol Chem. 2009 Oct 9;284(41):27964-27973. doi: 10.1074/jbc.M109.025296. Epub 2009 Aug 3. PMID: 19651782; PMCID: PMC2788848. 18: 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. PMID: 20809634. 19: 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. doi: 10.1016/j.bmcl.2006.11.030. Epub 2006 Nov 15. PMID: 17157012; PMCID: PMC1941685. 20: 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. doi: 10.1016/S0076-6879(05)07013-8. PMID: 16757321.