Thiomyristoyl | CAS#1429749-41-6 | SIRT2 inhibitor

MedKoo Cat#: 407437 | Name: Thiomyristoyl

Description:

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

Thiomyristoyl is a potent and specific SIRT2 inhibitor with an IC50 of 28 nM. IC50 & Target: IC50: 28 nM (SIRT2). Thiomyristoyl showed broad anticancer activity but little effect on non-cancerous cells.

Chemical Structure

Thiomyristoyl

CAS#1429749-41-6

Theoretical Analysis

MedKoo Cat#: 407437

Name: Thiomyristoyl

CAS#: 1429749-41-6

Chemical Formula: C34H51N3O3S

Exact Mass: 581.3651

Molecular Weight: 581.86

Elemental Analysis: C, 70.18; H, 8.84; N, 7.22; O, 8.25; S, 5.51

Price and Availability

Size	Price	Availability
10mg	USD 150.00	Ready to ship
25mg	USD 250.00	Ready to ship
50mg	USD 450.00	Ready to ship
100mg	USD 750.00	Ready to ship
200mg	USD 1,250.00	Ready to ship
500mg	USD 2,250.00	Ready to ship
1g	USD 3,650.00	Ready to ship
2g	USD 4,950.00	Ready to ship
5g	USD 9,650.00

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Related CAS #

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Synonym

Thiomyristoyl

IUPAC/Chemical Name

benzyl (S)-(1-oxo-1-(phenylamino)-6-tetradecanethioamidohexan-2-yl)carbamate

InChi Key

CJQGLLUJIVNREL-HKBQPEDESA-N

InChi Code

InChI=1S/C34H51N3O3S/c1-2-3-4-5-6-7-8-9-10-11-18-26-32(41)35-27-20-19-25-31(33(38)36-30-23-16-13-17-24-30)37-34(39)40-28-29-21-14-12-15-22-29/h12-17,21-24,31H,2-11,18-20,25-28H2,1H3,(H,35,41)(H,36,38)(H,37,39)/t31-/m0/s1

SMILES Code

O=C(OCC1=CC=CC=C1)N[C@@H](CCCCNC(CCCCCCCCCCCCC)=S)C(NC2=CC=CC=C2)=O

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

Certificate of Analysis

View CoA: current batch, Lot#A8T08K25

QC Data

View QC data: current batch, Lot#A8T08K25

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 581.86 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

1: He B, Hu J, Zhang X, Lin H. Thiomyristoyl peptides as cell-permeable Sirt6 inhibitors. Org Biomol Chem. 2014 Oct 14;12(38):7498-502. doi: 10.1039/c4ob00860j. PMID: 25163004; PMCID: PMC4161628. 2: Xu Y, Cai R, Zhao Z, Zhou L, Zhou Q, Hassan S, Huang S, Zhang M, Xu G, Zou X. Thiomyristoyl ameliorates colitis by blocking the differentiation of Th17 cells and inhibiting SIRT2-induced metabolic reprogramming. Int Immunopharmacol. 2021 Jan;90:107212. doi: 10.1016/j.intimp.2020.107212. Epub 2020 Dec 11. PMID: 33310666. 3: Wang Y, Fung YME, Zhang W, He B, Chung MWH, Jin J, Hu J, Lin H, Hao Q. Deacylation Mechanism by SIRT2 Revealed in the 1'-SH-2'-O-Myristoyl Intermediate Structure. Cell Chem Biol. 2017 Mar 16;24(3):339-345. doi: 10.1016/j.chembiol.2017.02.007. Epub 2017 Mar 9. PMID: 28286128; PMCID: PMC5365152. 4: Negrón Abril YL, Fernández I, Weiss RS. Assessment of SIRT2 Inhibitors in Mouse Models of Cancer. Methods Mol Biol. 2019;1983:151-171. doi: 10.1007/978-1-4939-9434-2_9. PMID: 31087297. 5: Spiegelman NA, Hong JY, Hu J, Jing H, Wang M, Price IR, Cao J, Yang M, Zhang X, Lin H. A Small-Molecule SIRT2 Inhibitor That Promotes K-Ras4a Lysine Fatty- Acylation. ChemMedChem. 2019 Apr 3;14(7):744-748. doi: 10.1002/cmdc.201800715. Epub 2019 Feb 25. PMID: 30734528; PMCID: PMC6452895. 6: Jing H, Hu J, He B, Negrón Abril YL, Stupinski J, Weiser K, Carbonaro M, Chiang YL, Southard T, Giannakakou P, Weiss RS, Lin H. A SIRT2-Selective Inhibitor Promotes c-Myc Oncoprotein Degradation and Exhibits Broad Anticancer Activity. Cancer Cell. 2016 Mar 14;29(3):297-310. doi: 10.1016/j.ccell.2016.02.007. Erratum in: Cancer Cell. 2016 Apr 11;29(4):607. doi: 10.1016/j.ccell.2016.03.011.. Giannakakou, Paraszkevi [corrected to Giannakakou, Paraskevi]. Erratum in: Cancer Cell. 2016 May 9;29(5):767-768. doi: 10.1016/j.ccell.2016.04.005. PMID: 26977881; PMCID: PMC4811675. 7: Teng YB, Jing H, Aramsangtienchai P, He B, Khan S, Hu J, Lin H, Hao Q. Efficient demyristoylase activity of SIRT2 revealed by kinetic and structural studies. Sci Rep. 2015 Feb 23;5:8529. doi: 10.1038/srep08529. PMID: 25704306; PMCID: PMC4894398. 8: Hong JY, Price IR, Bai JJ, Lin H. A Glycoconjugated SIRT2 Inhibitor with Aqueous Solubility Allows Structure-Based Design of SIRT2 Inhibitors. ACS Chem Biol. 2019 Aug 16;14(8):1802-1810. doi: 10.1021/acschembio.9b00384. Epub 2019 Aug 2. PMID: 31373792; PMCID: PMC6942458. 9: Zessin M, Kutil Z, Meleshin M, Nováková Z, Ghazy E, Kalbas D, Marek M, Romier C, Sippl W, Bařinka C, Schutkowski M. One-Atom Substitution Enables Direct and Continuous Monitoring of Histone Deacylase Activity. Biochemistry. 2019 Dec 3;58(48):4777-4789. doi: 10.1021/acs.biochem.9b00786. Epub 2019 Nov 14. PMID: 31682411. 10: Xu D, He H, Jiang X, Hua R, Chen H, Yang L, Cheng J, Duan J, Li Q. SIRT2 plays a novel role on progesterone, estradiol and testosterone synthesis via PPARs/LXRα pathways in bovine ovarian granular cells. J Steroid Biochem Mol Biol. 2019 Jan;185:27-38. doi: 10.1016/j.jsbmb.2018.07.005. Epub 2018 Aug 7. PMID: 30009951.