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MedKoo Cat#: 598683 | Name: Leukotriene C4

Description:

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

Leukotriene C4 is the conjugation product of LEUKOTRIENE A4 and glutathione. It is the major arachidonic acid metabolite in macrophages and human mast cells as well as in antigen-sensitized lung tissue. It stimulates mucus secretion in the lung, and produces contractions of nonvascular and some vascular smooth muscle.

Chemical Structure

Leukotriene C4
CAS#72025-60-6

Theoretical Analysis

MedKoo Cat#: 598683

Name: Leukotriene C4

CAS#: 72025-60-6

Chemical Formula: C30H47N3O9S

Exact Mass: 625.3033

Molecular Weight: 625.77

Elemental Analysis: C, 57.58; H, 7.57; N, 6.72; O, 23.01; S, 5.12

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Leukotriene C4; LTC4; Leukotriene C;
IUPAC/Chemical Name
(5S,6R,7E,9E,11Z,14Z)-6-(((R)-2-((S)-4-amino-4-carboxybutanamido)-3-((carboxymethyl)amino)-3-oxopropyl)thio)-5-hydroxyicosa-7,9,11,14-tetraenoic acid
InChi Key
GWNVDXQDILPJIG-NXOLIXFESA-N
InChi Code
InChI=1S/C30H47N3O9S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-25(24(34)15-14-17-27(36)37)43-21-23(29(40)32-20-28(38)39)33-26(35)19-18-22(31)30(41)42/h6-7,9-13,16,22-25,34H,2-5,8,14-15,17-21,31H2,1H3,(H,32,40)(H,33,35)(H,36,37)(H,38,39)(H,41,42)/b7-6-,10-9-,12-11+,16-13+/t22-,23-,24-,25+/m0/s1
SMILES Code
O=C(O)CNC([C@H](CS[C@@H]([C@@H](O)CCCC(O)=O)/C=C/C=C/C=C\C/C=C\CCCCC)NC(CC[C@@H](C(O)=O)N)=O)=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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 625.77 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: Dvash E, Har-Tal M, Barak S, Meir O, Rubinstein M. Leukotriene C4 is the major trigger of stress-induced oxidative DNA damage. Nat Commun. 2015 Dec 11;6:10112. doi: 10.1038/ncomms10112. PubMed PMID: 26656251; PubMed Central PMCID: PMC4682057. 2: MacDonald CA, Bushnell EA, Gauld JW, Boyd RJ. The catalytic formation of leukotriene C4: a critical step in inflammatory processes. Phys Chem Chem Phys. 2014 Aug 14;16(30):16284-9. doi: 10.1039/c4cp01984a. PubMed PMID: 24974917. 3: 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. 4: Hirata H, Arima M, Fukushima Y, Sugiyama K, Tokuhisa T, Fukuda T. Leukotriene C4 aggravates bleomycin-induced pulmonary fibrosis in mice. Respirology. 2013 May;18(4):674-81. doi: 10.1111/resp.12072. PubMed PMID: 23432979. 5: Niegowski D, Kleinschmidt T, Olsson U, Ahmad S, Rinaldo-Matthis A, Haeggström JZ. Crystal structures of leukotriene C4 synthase in complex with product analogs: implications for the enzyme mechanism. J Biol Chem. 2014 Feb 21;289(8):5199-207. doi: 10.1074/jbc.M113.534628. Epub 2013 Dec 23. PubMed PMID: 24366866; PubMed Central PMCID: PMC3931076. 6: Cabrera G, Fernández-Brando RJ, Mejías MP, Ramos MV, Abrey-Recalde MJ, Vanzulli S, Vermeulen M, Palermo MS. Leukotriene C4 increases the susceptibility of adult mice to Shiga toxin-producing Escherichia coli infection. Int J Med Microbiol. 2015 Dec;305(8):910-7. doi: 10.1016/j.ijmm.2015.09.006. Epub 2015 Sep 16. PubMed PMID: 26456732. 7: Bertin J, Jalaguier P, Barat C, Roy MA, Tremblay MJ. Exposure of human astrocytes to leukotriene C4 promotes a CX3CL1/fractalkine-mediated transmigration of HIV-1-infected CD4⁺ T cells across an in vitro blood-brain barrier model. Virology. 2014 Apr;454-455:128-38. doi: 10.1016/j.virol.2014.02.007. Epub 2014 Feb 28. PubMed PMID: 24725939. 8: Liu T, Garofalo D, Feng C, Lai J, Katz H, Laidlaw TM, Boyce JA. Platelet-driven leukotriene C4-mediated airway inflammation in mice is aspirin-sensitive and depends on T prostanoid receptors. J Immunol. 2015 Jun 1;194(11):5061-8. doi: 10.4049/jimmunol.1402959. Epub 2015 Apr 22. PubMed PMID: 25904552; PubMed Central PMCID: PMC4433852. 9: Cummings HE, Liu T, Feng C, Laidlaw TM, Conley PB, Kanaoka Y, Boyce JA. Cutting edge: Leukotriene C4 activates mouse platelets in plasma exclusively through the type 2 cysteinyl leukotriene receptor. J Immunol. 2013 Dec 15;191(12):5807-10. doi: 10.4049/jimmunol.1302187. Epub 2013 Nov 15. PubMed PMID: 24244016; PubMed Central PMCID: PMC3869987. 10: Xu R, Jin MH, Jiao Y, Xing GS, Zhao WJ, Zhao C, Duan HQ, Tang SA. Novel polyhydroxylated steroids from the East China Sea gorgonian Echinogorgia sassapo reticulata with suppressive activity of leukotriene C4 generation and degranulation in bone marrow-derived mast cells. J Asian Nat Prod Res. 2014;16(4):351-7. doi: 10.1080/10286020.2013.879469. Epub 2014 Jan 20. PubMed PMID: 24437431. 11: Seki K, Hisada T, Kawata T, Kamide Y, Dobashi K, Yamada M, Mori M, Okajima F, Ishizuka T. Oxidative stress potentially enhances FcεRI-mediated leukotriene C4 release dependent on the late-phase increase of intracellular glutathione in mast cells. Biochem Biophys Res Commun. 2013 Sep 27;439(3):357-62. doi: 10.1016/j.bbrc.2013.08.081. Epub 2013 Aug 30. PubMed PMID: 23998930. 12: Hong F, Yang S. Ischemic preconditioning decreased leukotriene C4 formation by depressing leukotriene C4 synthase expression and activity during hepatic I/R injury in rats. J Surg Res. 2012 Dec;178(2):1015-21. doi: 10.1016/j.jss.2012.07.061. Epub 2012 Aug 14. PubMed PMID: 22921920. 13: Jana B, Jaroszewski JJ, Czarzasta J, Markiewicz W. The influence of leukotrienes C₄ and D₄ on the contractility of an inflamed porcine uterus. Theriogenology. 2015 May;83(8):1328-37. doi: 10.1016/j.theriogenology.2015.01.021. Epub 2015 Jan 28. PubMed PMID: 25707327. 14: Dannull J, Schneider T, Lee WT, de Rosa N, Tyler DS, Pruitt SK. Leukotriene C4 induces migration of human monocyte-derived dendritic cells without loss of immunostimulatory function. Blood. 2012 Mar 29;119(13):3113-22. doi: 10.1182/blood-2011-10-385930. Epub 2012 Feb 8. PubMed PMID: 22323449; PubMed Central PMCID: PMC3321871. 15: Pereira-Vega A, Sánchez Ramos JL, Maldonado Pérez JA, Vázquez Oliva R, Bravo Nieto JM, Vázquez Rico I, Ignacio García JM, Romero Palacios P, Alwakil Olbah M, Medina Gallardo JF. Premenstrual asthma and leukotriene variations in the menstrual cycle. Allergol Immunopathol (Madr). 2012 Nov-Dec;40(6):368-73. doi: 10.1016/j.aller.2011.09.007. Epub 2011 Nov 23. PubMed PMID: 22115570. 16: Kanaoka Y, Maekawa A, Austen KF. Identification of GPR99 protein as a potential third cysteinyl leukotriene receptor with a preference for leukotriene E4 ligand. J Biol Chem. 2013 Apr 19;288(16):10967-72. doi: 10.1074/jbc.C113.453704. Epub 2013 Mar 15. PubMed PMID: 23504326; PubMed Central PMCID: PMC3630866. 17: Becher UM, Ghanem A, Tiyerili V, Fürst DO, Nickenig G, Mueller CF. Inhibition of leukotriene C4 action reduces oxidative stress and apoptosis in cardiomyocytes and impedes remodeling after myocardial injury. J Mol Cell Cardiol. 2011 Mar;50(3):570-7. doi: 10.1016/j.yjmcc.2010.11.013. Epub 2010 Nov 26. PubMed PMID: 21112334. 18: Fugazzola M, Barton AK, Niedorf F, Kietzmann M, Ohnesorge B. Non-genomic action of beclomethasone dipropionate on bronchoconstriction caused by leukotriene C4 in precision cut lung slices in the horse. BMC Vet Res. 2012 Sep 10;8:160. doi: 10.1186/1746-6148-8-160. PubMed PMID: 22963524; PubMed Central PMCID: PMC3485115. 19: Takase B, Kurita A, Maruyama T, Uehata A, Nishioka T, Mizuno K, Nakamura H, Katsura K, Kanda Y. Change of plasma leukotriene C4 during myocardial ischemia in humans. Clin Cardiol. 1996 Mar;19(3):198-204. PubMed PMID: 8674256. 20: Saino H, Ukita Y, Ago H, Irikura D, Nisawa A, Ueno G, Yamamoto M, Kanaoka Y, Lam BK, Austen KF, Miyano M. The catalytic architecture of leukotriene C4 synthase with two arginine residues. J Biol Chem. 2011 May 6;286(18):16392-401. doi: 10.1074/jbc.M110.150177. Epub 2011 Mar 16. PubMed PMID: 21454538; PubMed Central PMCID: PMC3091245.

View History

ST056083

ST056083

ST-1992

ST-1992

AS-4

AS-4