Hexylglutathione | CAS#24425-56-7 | glutathione-S-transferase inhibitor

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

MedKoo CAT#: 540197

CAS#: 24425-56-7

Description: Hexylglutathione is a glutathione-S-transferase inhibitor used to study the effects of phase II enzymes and glutathione.

Chemical Structure

Hexylglutathione

CAS# 24425-56-7

Instruction

Theoretical Analysis

MedKoo Cat#: 540197
Name: Hexylglutathione
CAS#: 24425-56-7
Chemical Formula: C16H29N3O6S
Exact Mass: 391.18
Molecular Weight: 391.480
Elemental Analysis: C, 49.09; H, 7.47; N, 10.73; O, 24.52; S, 8.19

Price and Availability

Size	Price	Availability
25mg	USD 350	2 Weeks
50mg	USD 550	2 Weeks
1g	USD 1250	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: NSC 131114; NSC131114; NSC-131114; S-Hexylglutathione

IUPAC/Chemical Name: N5-((R)-1-((carboxymethyl)amino)-3-(hexylthio)-1-oxopropan-2-yl)-L-glutamine

InChi Key: HXJDWCWJDCOHDG-RYUDHWBXSA-N

InChi Code: InChI=1S/C16H29N3O6S/c1-2-3-4-5-8-26-10-12(15(23)18-9-14(21)22)19-13(20)7-6-11(17)16(24)25/h11-12H,2-10,17H2,1H3,(H,18,23)(H,19,20)(H,21,22)(H,24,25)/t11-,12-/m0/s1

SMILES Code: O=C(O)CNC([C@H](CSCCCCCC)NC(CC[C@@H](C(O)=O)N)=O)=O

Appearance: Solid powder

Purity: >95% (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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 391.48 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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Swope MD, Sun HW, Klockow B, Blake P, Lolis E. Macrophage migration inhibitory factor interactions with glutathione and S-hexylglutathione. J Biol Chem. 1998 Jun 12;273(24):14877-84. PubMed PMID: 9614090.

2: Ortiz-Salmerón E, Nuccetelli M, Oakley AJ, Parker MW, Lo Bello M, García-Fuentes L. Thermodynamic description of the effect of the mutation Y49F on human glutathione transferase P1-1 in binding with glutathione and the inhibitor S-hexylglutathione. J Biol Chem. 2003 Nov 21;278(47):46938-48. Epub 2003 Aug 23. PubMed PMID: 12937169.

3: Reinemer P, Dirr HW, Ladenstein R, Huber R, Lo Bello M, Federici G, Parker MW. Three-dimensional structure of class pi glutathione S-transferase from human placenta in complex with S-hexylglutathione at 2.8 A resolution. J Mol Biol. 1992 Sep 5;227(1):214-26. PubMed PMID: 1522586.

4: Kajihara-Kano H, Hayakari M, Satoh K, Tomioka Y, Mizugaki M, Tsuchida S. Characterization of S-hexylglutathione-binding proteins of human hepatocellular carcinoma: separation of enoyl-CoA isomerase from an Alpha class glutathione transferase form. Biochem J. 1997 Dec 1;328 ( Pt 2):473-8. PubMed PMID: 9371703; PubMed Central PMCID: PMC1218943.

5: Hayes JD. Purification and physical characterization of glutathione S-transferase K. Differential use of S-hexylglutathione and glutathione affinity matrices to isolate a novel glutathione S-transferase from rat liver. Biochem J. 1986 Feb 1;233(3):789-98. PubMed PMID: 3707526; PubMed Central PMCID: PMC1153100.

6: Erhardt J, Dirr H. Effect of glutathione, glutathione sulphonate and S-hexylglutathione on the conformational stability of class pi glutathione S-transferase. FEBS Lett. 1996 Aug 12;391(3):313-6. PubMed PMID: 8764997.

7: Takahashi Y, Hirata Y, Burstein Y, Listowsky I. Delta 3, delta 2-enoyl-CoA isomerase is the protein that copurifies with human glutathione S-transferases from S-hexylglutathione affinity matrices. Biochem J. 1994 Dec 15;304 ( Pt 3):849-52. PubMed PMID: 7818490; PubMed Central PMCID: PMC1137411.

8: Yonetomi Y, Sekioka T, Kadode M, Kitamine T, Kamiya A, Matsumura N, Fujita M, Kawabata K. Leukotriene C4 induces bronchoconstriction and airway vascular hyperpermeability via the cysteinyl leukotriene receptor 2 in S-hexyl glutathione-treated guinea pigs. Eur J Pharmacol. 2015 May 5;754:98-104. doi: 10.1016/j.ejphar.2015.02.014. Epub 2015 Feb 20. PubMed PMID: 25704617.

9: Yang XQ, Zhang YL. Characterization of glutathione S-transferases from Sus scrofa, Cydia pomonella and Triticum aestivum: their responses to cantharidin. Enzyme Microb Technol. 2015 Feb;69:1-9. doi: 10.1016/j.enzmictec.2014.11.003. Epub 2014 Nov 24. PubMed PMID: 25640718.

10: Tshabalala TN, Tomescu MS, Prior A, Balakrishnan V, Sayed Y, Dirr HW, Achilonu I. Energetics of Glutathione Binding to Human Eukaryotic Elongation Factor 1 Gamma: Isothermal Titration Calorimetry and Molecular Dynamics Studies. Protein J. 2016 Dec;35(6):448-458. PubMed PMID: 27844275.

11: Hayes JD. Selective elution of rodent glutathione S-transferases and glyoxalase I from the S-hexyglutathione-Sepharose affinity matrix. Biochem J. 1988 Nov 1;255(3):913-22. PubMed PMID: 3214431; PubMed Central PMCID: PMC1135328.

12: Yu J, Li C, Shen S, Liu X, Peng Y, Zheng J. Mass spectrometry based detection of glutathione with sensitivity for single-cell analysis. Rapid Commun Mass Spectrom. 2015 Apr 15;29(7):681-9. doi: 10.1002/rcm.7148. PubMed PMID: 26212287.

13: Kim JG, Ahn CS, Kim SH, Bae YA, Kwon NY, Kang I, Yang HJ, Sohn WM, Kong Y. Clonorchis sinensis omega-class glutathione transferases play major roles in the protection of the reproductive system during maturation and the response to oxidative stress. Parasit Vectors. 2016 Jun 13;9(1):337. doi: 10.1186/s13071-016-1622-2. PubMed PMID: 27296469; PubMed Central PMCID: PMC4906895.

14: Allen RE, Lo TW, Thornalley PJ. A simplified method for the purification of human red blood cell glyoxalase. I. Characteristics, immunoblotting, and inhibitor studies. J Protein Chem. 1993 Apr;12(2):111-9. PubMed PMID: 8489699.

15: Kuhnert DC, Sayed Y, Mosebi S, Sayed M, Sewell T, Dirr HW. Tertiary interactions stabilise the C-terminal region of human glutathione transferase A1-1: a crystallographic and calorimetric study. J Mol Biol. 2005 Jun 17;349(4):825-38. PubMed PMID: 15893769.

16: Thévenin AF, Zony CL, Bahnson BJ, Colman RF. GST pi modulates JNK activity through a direct interaction with JNK substrate, ATF2. Protein Sci. 2011 May;20(5):834-48. doi: 10.1002/pro.609. Epub 2011 Mar 23. PubMed PMID: 21384452; PubMed Central PMCID: PMC3125868.

17: Mosialou E, Morgenstern R. Inhibition studies on rat liver microsomal glutathione transferase. Chem Biol Interact. 1990;74(3):275-80. PubMed PMID: 2347005.

18: Mannervik B, Guthenberg C. Glutathione transferase (human placenta). Methods Enzymol. 1981;77:231-5. PubMed PMID: 7329301.

19: Katusz RM, Colman RF. S-(4-Bromo-2,3-dioxobutyl)glutathione: a new affinity label for the 4-4 isoenzyme of rat liver glutathione S-transferase. Biochemistry. 1991 Nov 26;30(47):11230-8. PubMed PMID: 1958660.

20: Andersson C, Morgenstern R. Chemical modification of rat liver microsomal glutathione transferase defines residues of importance for catalytic function. Biochem J. 1990 Dec 1;272(2):479-84. PubMed PMID: 2268274; PubMed Central PMCID: PMC1149725.

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Hexylglutathione featured