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MedKoo Cat#: 466168 | Name: REV5901

Description:

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

REV5901 is the first reported dual inhibitor of cysteinyl leukotriene receptor 1 (CysLT1R) and G-protein-coupled bile acid receptor 1 (GPBAR1).

Chemical Structure

REV5901
REV5901
CAS#101910-24-1

Theoretical Analysis

MedKoo Cat#: 466168

Name: REV5901

CAS#: 101910-24-1

Chemical Formula: C22H25NO2

Exact Mass: 335.1885

Molecular Weight: 335.45

Elemental Analysis: C, 78.77; H, 7.51; N, 4.18; O, 9.54

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 #
No Data
Synonym
REV5901; REV 5901; REV-5901;
IUPAC/Chemical Name
1-(3-(quinolin-2-ylmethoxy)phenyl)hexan-1-ol
InChi Key
JRLOEMCOOZSCQP-UHFFFAOYSA-N
InChi Code
InChI=1S/C22H25NO2/c1-2-3-4-12-22(24)18-9-7-10-20(15-18)25-16-19-14-13-17-8-5-6-11-21(17)23-19/h5-11,13-15,22,24H,2-4,12,16H2,1H3
SMILES Code
CCCCCC(C1=CC=CC(OCC2=NC3=CC=CC=C3C=C2)=C1)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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 335.45 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: Biagioli M, Carino A, Marchianò S, Roselli R, Di Giorgio C, Bordoni M, Fiorucci C, Sepe V, Conflitti P, Limongelli V, Distrutti E, Baldoni M, Zampella A, Fiorucci S. Identification of cysteinyl-leukotriene-receptor 1 antagonists as ligands for the bile acid receptor GPBAR1. Biochem Pharmacol. 2020 Jul;177:113987. doi: 10.1016/j.bcp.2020.113987. Epub 2020 Apr 21. PMID: 32330496. 2: Kuhnert R, Sárosi MB, George S, Lönnecke P, Hofmann B, Steinhilber D, Murganic B, Mijatovic S, Maksimovic-Ivanic D, Hey-Hawkins E. CarbORev-5901: The First Carborane-Based Inhibitor of the 5-Lipoxygenase Pathway. ChemMedChem. 2017 Jul 6;12(13):1081-1086. doi: 10.1002/cmdc.201700309. Epub 2017 Jun 21. PMID: 28569429. 3: Huang YH, Sharifpanah F, Becker S, Wartenberg M, Sauer H. Impact of Arachidonic Acid and the Leukotriene Signaling Pathway on Vasculogenesis of Mouse Embryonic Stem Cells. Cells Tissues Organs. 2016;201(5):319-32. doi: 10.1159/000445680. Epub 2016 May 21. PMID: 27198524. 4: Wang Z, Irianto J, Kazun S, Wang W, Knight MM. The rate of hypo-osmotic challenge influences regulatory volume decrease (RVD) and mechanical properties of articular chondrocytes. Osteoarthritis Cartilage. 2015 Feb;23(2):289-99. doi: 10.1016/j.joca.2014.11.003. Epub 2014 Nov 11. PMID: 25450844. 5: Qusous A, Parker E, Ali N, Mohmand SG, Kerrigan MJ. The effects of REV5901 on intracellular calcium signalling in freshly isolated bovine articular chondrocytes. Gen Physiol Biophys. 2012 Sep;31(3):299-307. doi: 10.4149/gpb_2012_035. PMID: 23047943. 6: Qusous A, Kerrigan MJ. Quantification of Changes in Morphology, Mechanotransduction, and Gene Expression in Bovine Articular Chondrocytes in Response to 2-Dimensional Culture Indicates the Existence of a Novel Phenotype. Cartilage. 2012 Jul;3(3):222-34. doi: 10.1177/1947603511427556. PMID: 26069635; PMCID: PMC4297122. 7: Qusous A, Parker E, Geewan C, Kapasi A, Getting SJ, Hucklebridge F, Keshavarz T, Kerrigan MJ. Novel methods for the quantification of changes in actin organization in chondrocytes using fluorescent imaging and linear profiling. Microsc Res Tech. 2012 Jul;75(7):991-9. doi: 10.1002/jemt.22055. Epub 2012 Apr 19. PMID: 22514026. 8: Fischer AS, Metzner J, Steinbrink SD, Ulrich S, Angioni C, Geisslinger G, Steinhilber D, Maier TJ. 5-Lipoxygenase inhibitors induce potent anti- proliferative and cytotoxic effects in human tumour cells independently of suppression of 5-lipoxygenase activity. Br J Pharmacol. 2010 Oct;161(4):936-49. doi: 10.1111/j.1476-5381.2010.00915.x. PMID: 20860670; PMCID: PMC2992906. 9: Lee SJ, Kim CE, Yun MR, Seo KW, Park HM, Yun JW, Shin HK, Bae SS, Kim CD. 4-Hydroxynonenal enhances MMP-9 production in murine macrophages via 5-lipoxygenase-mediated activation of ERK and p38 MAPK. Toxicol Appl Pharmacol. 2010 Jan 15;242(2):191-8. doi: 10.1016/j.taap.2009.10.007. Epub 2009 Oct 22. PMID: 19837106. 10: Seo KW, Lee SJ, Kim CE, Yun MR, Park HM, Yun JW, Bae SS, Kim CD. Participation of 5-lipoxygenase-derived LTB(4) in 4-hydroxynonenal-enhanced MMP-2 production in vascular smooth muscle cells. Atherosclerosis. 2010 Jan;208(1):56-61. doi: 10.1016/j.atherosclerosis.2009.06.012. Epub 2009 Jun 18. PMID: 19586628. 11: Tarcan T, Ozdemir I, Onol FF. The role of alpha1-adrenoceptor and arachidonate pathways in increased tone of demucosalized bladder tissue. J Urol. 2009 Jun;181(6):2780-9. doi: 10.1016/j.juro.2009.01.099. Epub 2009 Apr 17. PMID: 19375733. 12: Melstrom LG, Bentrem DJ, Salabat MR, Kennedy TJ, Ding XZ, Strouch M, Rao SM, Witt RC, Ternent CA, Talamonti MS, Bell RH, Adrian TA. Overexpression of 5-lipoxygenase in colon polyps and cancer and the effect of 5-LOX inhibitors in vitro and in a murine model. Clin Cancer Res. 2008 Oct 15;14(20):6525-30. doi: 10.1158/1078-0432.CCR-07-4631. PMID: 18927292. 13: Kerrigan MJ, Hall AC. Control of chondrocyte regulatory volume decrease (RVD) by [Ca2+]i and cell shape. Osteoarthritis Cartilage. 2008 Mar;16(3):312-22. doi: 10.1016/j.joca.2007.07.006. Epub 2007 Sep 12. PMID: 17855127. 14: Schroeder CP, Yang P, Newman RA, Lotan R. Simultaneous inhibition of COX-2 and 5-LOX activities augments growth arrest and death of premalignant and malignant human lung cell lines. J Exp Ther Oncol. 2007;6(3):183-92. PMID: 17552358. 15: Nieves D, Moreno JJ. Role of 5-lipoxygenase pathway in the regulation of RAW 264.7 macrophage proliferation. Biochem Pharmacol. 2006 Oct 16;72(8):1022-30. doi: 10.1016/j.bcp.2006.07.021. Epub 2006 Aug 28. PMID: 16934759. 16: Carraway RE, Hassan S, Cochrane DE. Regulation of neurotensin receptor function by the arachidonic acid-lipoxygenase pathway in prostate cancer PC3 cells. Prostaglandins Leukot Essent Fatty Acids. 2006 Feb;74(2):93-107. doi: 10.1016/j.plefa.2005.11.005. Epub 2006 Jan 6. PMID: 16406549. 17: Hennig R, Grippo P, Ding XZ, Rao SM, Buchler MW, Friess H, Talamonti MS, Bell RH, Adrian TE. 5-Lipoxygenase, a marker for early pancreatic intraepithelial neoplastic lesions. Cancer Res. 2005 Jul 15;65(14):6011-6. doi: 10.1158/0008-5472.CAN-04-4090. PMID: 16024599. 18: Jeon SB, Ji KA, You HJ, Kim JH, Jou I, Joe EH. Nordihydroguaiaretic acid inhibits IFN-gamma-induced STAT tyrosine phosphorylation in rat brain astrocytes. Biochem Biophys Res Commun. 2005 Mar 11;328(2):595-600. doi: 10.1016/j.bbrc.2005.01.025. PMID: 15694390. 19: Hoque A, Lippman SM, Wu TT, Xu Y, Liang ZD, Swisher S, Zhang H, Cao L, Ajani JA, Xu XC. Increased 5-lipoxygenase expression and induction of apoptosis by its inhibitors in esophageal cancer: a potential target for prevention. Carcinogenesis. 2005 Apr;26(4):785-91. doi: 10.1093/carcin/bgi026. Epub 2005 Jan 20. PMID: 15661803. 20: Azadzoi KM, Shinde VM, Tarcan T, Kozlowski R, Siroky MB. Increased leukotriene and prostaglandin release, and overactivity in the chronically ischemic bladder. J Urol. 2003 May;169(5):1885-91. doi: 10.1097/01.ju.0000048668.97821.f4. PMID: 12686867.

View History

CB 3988

CB 3988