GYY 4137 morpholine | CAS#106740-09-4 | Slow-releasing H2S donor

MedKoo Cat#: 206457 | Name: GYY 4137 morpholine salt

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Description:

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

GYY4137 is a novel water-soluble and slow releasing H2S donor. Hydrogen sulfide (H2S) is now recognized as the so called "third gasotransmitter" taking its place alongside nitric oxide and carbon monoxide. GYY4137 protects against myocardial ischemia and reperfusion injury by attenuating oxidative stress and apoptosis in rats. GYY4137 inhibits the inflammatory response by suppressing the activation of nuclear factor-kappa B and mitogen-activated protein kinases in Coxsackie virus B3-infected rat cardiomyocytes. GYY4137 exhibits potent anti-cancer activity by releasing H2S over a period of days.

Chemical Structure

GYY 4137 morpholine salt

CAS#106740-09-4

Theoretical Analysis

MedKoo Cat#: 206457

Name: GYY 4137 morpholine salt

CAS#: 106740-09-4

Chemical Formula: C15H25N2O3PS2

Exact Mass: 376.1044

Molecular Weight: 376.47

Elemental Analysis: C, 47.86; H, 6.69; N, 7.44; O, 12.75; P, 8.23; S, 17.03

Price and Availability

Size	Price	Availability
10mg	USD 285.00	2 Weeks
25mg	USD 550.00	2 Weeks
50mg	USD 850.00	2 Weeks

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Synonym

GYY4137; GYY-4137; GYY 4137; GYY 4137 morpholine salt;

IUPAC/Chemical Name

morpholine (4-methoxyphenyl)(morpholino)phosphinodithioate

InChi Key

YZMHNNLDUWRZFW-UHFFFAOYSA-N

InChi Code

InChI=1S/C11H16NO2PS2.C4H9NO/c1-13-10-2-4-11(5-3-10)15(16,17)12-6-8-14-9-7-12;1-3-6-4-2-5-1/h2-5H,6-9H2,1H3,(H,16,17);5H,1-4H2

SMILES Code

SP(N1CCOCC1)(C2=CC=C(OC)C=C2)=S.N3CCOCC3

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, soluble in water

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

Preparing Stock Solutions

The following data is based on the product molecular weight 376.47 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: Meng G, Zhu J, Xiao Y, Huang Z, Zhang Y, Tang X, Xie L, Chen Y, Shao Y, Ferro A, Wang R, Moore PK, Ji Y. Hydrogen Sulfide Donor GYY4137 Protects against Myocardial Fibrosis. Oxid Med Cell Longev. 2015;2015:691070. doi: 10.1155/2015/691070. Epub 2015 May 11. PubMed PMID: 26078813; PubMed Central PMCID: PMC4442292. 2: Meng G, Wang J, Xiao Y, Bai W, Xie L, Shan L, Moore PK, Ji Y. GYY4137 protects against myocardial ischemia and reperfusion injury by attenuating oxidative stress and apoptosis in rats. J Biomed Res. 2015 May;29(3):203-13. doi: 10.7555/JBR.28.20140037. Epub 2014 Oct 10. Review. PubMed PMID: 26060444; PubMed Central PMCID: PMC4449488. 3: Rose P, Dymock BW, Moore PK. GYY4137, a novel water-soluble, H2S-releasing molecule. Methods Enzymol. 2015;554:143-67. doi: 10.1016/bs.mie.2014.11.014. Epub 2015 Jan 10. PubMed PMID: 25725521. 4: Jiang X, Chen Y, Lu K, Zhang H, Fan X. GYY4137 promotes bone formation in a rabbit distraction osteogenesis model: a preliminary report. J Oral Maxillofac Surg. 2015 Apr;73(4):732.e1-6. doi: 10.1016/j.joms.2014.11.012. Epub 2014 Dec 27. PubMed PMID: 25661504. 5: Wu Z, Peng H, Du Q, Lin W, Liu Y. GYY4137, a hydrogen sulfide releasing molecule, inhibits the inflammatory response by suppressing the activation of nuclear factor kappa B and mitogen activated protein kinases in Coxsackie virus B3 infected rat cardiomyocytes. Mol Med Rep. 2015 Mar;11(3):1837-44. doi: 10.3892/mmr.2014.2901. Epub 2014 Nov 7. PubMed PMID: 25377925. 6: Lu S, Gao Y, Huang X, Wang X. GYY4137, a hydrogen sulfide (H₂S) donor, shows potent anti-hepatocellular carcinoma activity through blocking the STAT3 pathway. Int J Oncol. 2014 Apr;44(4):1259-67. doi: 10.3892/ijo.2014.2305. Epub 2014 Feb 14. PubMed PMID: 24535538. 7: Wei WB, Hu X, Zhuang XD, Liao LZ, Li WD. GYY4137, a novel hydrogen sulfide-releasing molecule, likely protects against high glucose-induced cytotoxicity by activation of the AMPK/mTOR signal pathway in H9c2 cells. Mol Cell Biochem. 2014 Apr;389(1-2):249-56. doi: 10.1007/s11010-013-1946-6. Epub 2013 Dec 28. PubMed PMID: 24374752. 8: Chitnis MK, Njie-Mbye YF, Opere CA, Wood ME, Whiteman M, Ohia SE. Pharmacological actions of the slow release hydrogen sulfide donor GYY4137 on phenylephrine-induced tone in isolated bovine ciliary artery. Exp Eye Res. 2013 Nov;116:350-4. doi: 10.1016/j.exer.2013.10.004. Epub 2013 Oct 18. PubMed PMID: 24145109. 9: Liu Z, Han Y, Li L, Lu H, Meng G, Li X, Shirhan M, Peh MT, Xie L, Zhou S, Wang X, Chen Q, Dai W, Tan CH, Pan S, Moore PK, Ji Y. The hydrogen sulfide donor, GYY4137, exhibits anti-atherosclerotic activity in high fat fed apolipoprotein E(-/-) mice. Br J Pharmacol. 2013 Aug;169(8):1795-809. doi: 10.1111/bph.12246. PubMed PMID: 23713790; PubMed Central PMCID: PMC3753836. 10: Grambow E, Mueller-Graf F, Delyagina E, Frank M, Kuhla A, Vollmar B. Effect of the hydrogen sulfide donor GYY4137 on platelet activation and microvascular thrombus formation in mice. Platelets. 2014;25(3):166-74. doi: 10.3109/09537104.2013.786823. Epub 2013 Apr 15. PubMed PMID: 23586391. 11: Li L, Fox B, Keeble J, Salto-Tellez M, Winyard PG, Wood ME, Moore PK, Whiteman M. The complex effects of the slow-releasing hydrogen sulfide donor GYY4137 in a model of acute joint inflammation and in human cartilage cells. J Cell Mol Med. 2013 Mar;17(3):365-76. doi: 10.1111/jcmm.12016. Epub 2013 Jan 28. PubMed PMID: 23356870; PubMed Central PMCID: PMC3823018. 12: Robinson H, Wray S. A new slow releasing, H₂S generating compound, GYY4137 relaxes spontaneous and oxytocin-stimulated contractions of human and rat pregnant myometrium. PLoS One. 2012;7(9):e46278. doi: 10.1371/journal.pone.0046278. Epub 2012 Sep 27. PubMed PMID: 23029460; PubMed Central PMCID: PMC3459845. 13: Lee ZW, Zhou J, Chen CS, Zhao Y, Tan CH, Li L, Moore PK, Deng LW. The slow-releasing hydrogen sulfide donor, GYY4137, exhibits novel anti-cancer effects in vitro and in vivo. PLoS One. 2011;6(6):e21077. doi: 10.1371/journal.pone.0021077. Epub 2011 Jun 20. PubMed PMID: 21701688; PubMed Central PMCID: PMC3119065. 14: Yu F, Zhao J, Tang CS, Geng B. [Effect of synthesized GYY4137, a slowly releasing hydrogen sulfide donor, on cell viability and distribution of hydrogen sulfide in mice]. Beijing Da Xue Xue Bao. 2010 Oct 18;42(5):493-7. Chinese. PubMed PMID: 20957002. 15: Li L, Salto-Tellez M, Tan CH, Whiteman M, Moore PK. GYY4137, a novel hydrogen sulfide-releasing molecule, protects against endotoxic shock in the rat. Free Radic Biol Med. 2009 Jul 1;47(1):103-13. doi: 10.1016/j.freeradbiomed.2009.04.014. Epub 2009 Apr 15. PubMed PMID: 19375498. 16: Li L, Whiteman M, Guan YY, Neo KL, Cheng Y, Lee SW, Zhao Y, Baskar R, Tan CH, Moore PK. Characterization of a novel, water-soluble hydrogen sulfide-releasing molecule (GYY4137): new insights into the biology of hydrogen sulfide. Circulation. 2008 May 6;117(18):2351-60. doi: 10.1161/CIRCULATIONAHA.107.753467. Epub 2008 Apr 28. PubMed PMID: 18443240.