WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 526761
CAS#: 132836-42-1 (anhydrous)
Description: YS-49 is an anti-inflammatory agent and activator of PI3K/Akt signaling. YS-49 regulates angiotensin II-stimulated ROS production, JNK phosphorylation and vascular smooth muscle cell proliferation via the induction of heme oxygenase-1. YS 49 induced HO-1 protein production in a dose-and time-dependent manner in VSMCs. Treatment with YS 49 significantly and dose-dependently inhibited Ang II-induced VSMC proliferation, ROS production, and phosphorylation of JNK, but not P38 MAP kinase or ERK1/2. YS 49 has potential as a therapeutic strategy for the pathogenesis of Ang II-related vascular diseases such as hypertension and atherosclerosis, via the induction of HO-1 gene activity.
MedKoo Cat#: 526761
Name: YS-49 HBr hydrate
CAS#: 132836-42-1 (anhydrous)
Chemical Formula: C20H22BrNO3
Exact Mass: 305.1416
Molecular Weight: 404.304
Elemental Analysis: C, 59.42; H, 5.48; Br, 19.76; N, 3.46; O, 11.87
Related CAS #: 132836-42-1 (anhydrous)
Synonym: YS-49; YS49; YS 49; YS-49 HBr hydrate; YS-49 hydrobromide monohydrate;
IUPAC/Chemical Name: 1,2,3,4-Tetrahydro-1-(1-naphthalenylmethyl)-6,7-Isoquinolinediol hydrobromide monohydrate
InChi Key: QHCUNMLYODPTIU-UHFFFAOYSA-N
InChi Code: InChI=1S/C20H19NO2.BrH.H2O/c22-19-11-15-8-9-21-18(17(15)12-20(19)23)10-14-6-3-5-13-4-1-2-7-16(13)14;;/h1-7,11-12,18,21-23H,8-10H2;1H;1H2
SMILES Code: OC1=CC2=C(C(CC3=C4C=CC=CC4=CC=C3)NCC2)C=C1O.[H]Br.[H]O[H]
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
The following data is based on the product molecular weight 404.304 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: Lee WS, Yun JW, Nagappan A, Lu JN, Kim MJ, Lee JH, Kim DH, Choi YH, Kim HJ, Chang KC, Jung JM. Synthesized tetrahydroisoquinoline alkaloid exerts anticancer effects at least in part by suppressing NF-κB-regulated proteins in A549 human lung cancer cells. Oncol Rep. 2015 Mar;33(3):1141-6. doi: 10.3892/or.2014.3658. Epub 2014 Dec 8. PubMed PMID: 25482101.
2: Kim YM, Tsoyi K, Jang HJ, Park EJ, Park SW, Kim HJ, Hwa JS, Chang KC. CKD712, a synthetic isoquinoline alkaloid, enhances the anti-cancer effects of paclitaxel in MDA-MB-231 cells through regulation of PTEN. Life Sci. 2014 Sep 1;112(1-2):49-58. doi: 10.1016/j.lfs.2014.07.015. Epub 2014 Jul 21. PubMed PMID: 25058922.
3: Hsu YH, Chang CC, Yang NJ, Lee YH, Juan SH. RhoA-mediated inhibition of vascular endothelial cell mobility: positive feedback through reduced cytosolic p21 and p27. J Cell Physiol. 2014 Oct;229(10):1455-65. doi: 10.1002/jcp.24583. PubMed PMID: 24535918.
4: Choi JM, Choi YH, Kim SK, Ahn KH, Won JH, Lim JH, Jang YJ, Lee S, Kim DH, Kim DK. (S)-tetrahydroisoquinoline alkaloid inhibits LPS-induced arachidonic acid release through downregulation of cPLA2 expression. Mol Cells. 2013 Nov;36(5):400-9. doi: 10.1007/s10059-013-0078-x. Epub 2013 Nov 14. PubMed PMID: 24293010; PubMed Central PMCID: PMC3887938.
5: Sharma S, Singh M, Sharma PL. Mechanism of hyperhomocysteinemia-induced vascular endothelium dysfunction - possible dysregulation of phosphatidylinositol-3-kinase and its downstream phosphoinositide dependent kinase and protein kinase B. Eur J Pharmacol. 2013 Dec 5;721(1-3):365-72. doi: 10.1016/j.ejphar.2013.08.028. Epub 2013 Sep 8. PubMed PMID: 24021535.
6: Jang HJ, Tsoyi K, Kim YM, Park EJ, Park SW, Kim HJ, Lee JH, Chang KC. (S)-1-α-naphthylmethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (CKD712), promotes wound closure by producing VEGF through HO-1 induction in human dermal fibroblasts and mouse skin. Br J Pharmacol. 2013 Mar;168(6):1485-96. doi: 10.1111/bph.12031. PubMed PMID: 23088309; PubMed Central PMCID: PMC3596652.
7: Park JH, Hwang IC, Ha N, Lee S, Kim JM, Lee SS, Yu H, Lim IT, You JA, Kim DH. Effects of the anti-sepsis drug, (S)-1-(α-naphthylmethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (CKD-712), on mortality, inflammation, and organ injuries in rodent sepsis models. Arch Pharm Res. 2011 Mar;34(3):485-94. doi: 10.1007/s12272-011-0318-6. Epub 2011 May 6. PubMed PMID: 21547682.
8: Im DS. A promising anti-inflammatory and anti-thrombotic drug for sepsis treatment. Arch Pharm Res. 2011 Mar;34(3):339-42. doi: 10.1007/s12272-011-0300-3. PubMed PMID: 21547664.
9: Oh YJ, Youn JH, Min HJ, Kim DH, Lee SS, Choi IH, Shin JS. CKD712, (S)-1-(α-naphthylmethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, inhibits the lipopolysaccharide-stimulated secretion of HMGB1 by inhibiting PI3K and classical protein kinase C. Int Immunopharmacol. 2011 Sep;11(9):1160-5. doi: 10.1016/j.intimp.2011.03.013. Epub 2011 Mar 30. PubMed PMID: 21457762.
10: Tsoyi K, Kim WS, Kim YM, Kim HJ, Seo HG, Lee JH, Yun-Choi HS, Chang KC. Upregulation of PTEN by CKD712, a synthetic tetrahydroisoquinoline alkaloid, selectively inhibits lipopolysaccharide-induced VCAM-1 but not ICAM-1 expression in human endothelial cells. Atherosclerosis. 2009 Dec;207(2):412-9. doi: 10.1016/j.atherosclerosis.2009.05.012. Epub 2009 May 21. PubMed PMID: 19540498.
11: Jin YC, Lee YS, Kim YM, Seo HG, Lee JH, Kim HJ, Yun-Choi HS, Chang KC. (S)-1-(alpha-naphthylmethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (CKD712) reduces rat myocardial apoptosis against ischemia and reperfusion injury by activation of phosphatidylinositol 3-kinase/Akt signaling and anti-inflammatory action in vivo. J Pharmacol Exp Ther. 2009 Aug;330(2):440-8. doi: 10.1124/jpet.108.150342. Epub 2009 May 20. PubMed PMID: 19458286.
12: Tsoyi K, Kim HJ, Shin JS, Kim DH, Cho HJ, Lee SS, Ahn SK, Yun-Choi HS, Lee JH, Seo HG, Chang KC. HO-1 and JAK-2/STAT-1 signals are involved in preferential inhibition of iNOS over COX-2 gene expression by newly synthesized tetrahydroisoquinoline alkaloid, CKD712, in cells activated with lipopolysacchride. Cell Signal. 2008 Oct;20(10):1839-47. doi: 10.1016/j.cellsig.2008.06.012. Epub 2008 Jun 27. PubMed PMID: 18634870.
13: Sun JJ, Kim HJ, Seo HG, Lee JH, Yun-Choi HS, Chang KC. YS 49, 1-(alpha-naphtylmethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, regulates angiotensin II-stimulated ROS production, JNK phosphorylation and vascular smooth muscle cell proliferation via the induction of heme oxygenase-1. Life Sci. 2008 Mar 12;82(11-12):600-7. doi: 10.1016/j.lfs.2007.12.015. Epub 2007 Dec 26. PubMed PMID: 18262205.
14: Pyo MK, Kim JM, Jin JL, Chang KC, Lee DH, Yun-Choi HS. Effects of higenamine and its 1-naphthyl analogs, YS-49 and YS-51, on platelet TXA2 synthesis and aggregation. Thromb Res. 2007;120(1):81-6. Epub 2006 Oct 3. PubMed PMID: 17020781.
15: Pyo MK, Yun-Choi HS, Chang KC, Lee DH. Effects of two tetrahydroisoquinolines (YS-49 and YS-51) on experimental disseminated intravascular coagulation induced by lipopolysaccharide in rats. Arzneimittelforschung. 2004;54(11):705-10. PubMed PMID: 15612611.
16: Kang YJ, Seo SJ, Yun-Choi HS, Lee DH, Kim YM, Chang KC. A synthetic isoquinoline alkaloid, 1-(beta-naphthylmethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (YS 51), reduces inducible nitric oxide synthase expression and improves survival in a rodent model of endotoxic shock. J Pharmacol Exp Ther. 2002 May;301(2):561-7. PubMed PMID: 11961057.
17: Yun-Choi HS, Pyo MK, Park KM, Chang KC, Lee DH. Antithrombotic effects of YS-49 and YS-51--1-naphthylmethyl analogs of higenamine. Thromb Res. 2001 Nov 15;104(4):249-55. PubMed PMID: 11728526.
18: Kang YJ, Koo EB, Lee YS, Yun-Choi HS, Chang KC. Prevention of the expression of inducible nitric oxide synthase by a novel positive inotropic agent, YS 49, in rat vascular smooth muscle and RAW 264.7 macrophages. Br J Pharmacol. 1999 Sep;128(2):357-64. PubMed PMID: 10510445; PubMed Central PMCID: PMC1571637.
19: Lee YS, Kim CH, Yun-Choi HS, Chang KC. Cardiovascular effect of a naphthylmethyl substituted tetrahydroisoquinoline, YS 49, in rat and rabbit. Life Sci. 1994;55(21):PL415-20. PubMed PMID: 7968232.
20: Yong TS, Chung PR, Lee KT. [Electron-microscopic studies on fine structure and enzyme activity in the axenic and conventional strains of Entamoeba histolytica]. Kisaengchunghak Chapchi. 1985 Dec;23(2):269-284. Korean. PubMed PMID: 12888671.