CKD-712 | CAS#626252-75-3 | NF-Kappa B Inhibitor

MedKoo Cat#: 528307 | Name: CKD-712

Description:

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

CKD-712 is a nuclear factor NF-kappa B inhibitor potentially for the treatment of sepsis. CKD-712 induced cell growth arrest, and inhibited the invasion and motility of A549 cells as determined by cell cycle analysis, a Matrigel-coated chamber assay, and a wound-healing assay, respectively. CKD-712 suppressed MMP-9, but not MMP-2 and other NF-κB-regulated proteins involved in cancer metastasis such as VEGF. CKD-712 induced cell cycle arrest at G2M phase by suppressing cyclin A, cyclin B and CDK-1 expression.

Chemical Structure

CKD-712

CAS#626252-75-3

Theoretical Analysis

MedKoo Cat#: 528307

Name: CKD-712

CAS#: 626252-75-3

Chemical Formula: C20H19NO2

Exact Mass: 305.1416

Molecular Weight: 305.38

Elemental Analysis: C, 78.66; H, 6.27; N, 4.59; O, 10.48

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

CKD-712; CKD 712; CKD712

IUPAC/Chemical Name

(S)-1-(naphthalen-1-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol

InChi Key

YGCQFKVNIBDJFW-SFHVURJKSA-N

InChi Code

InChI=1S/C20H19NO2/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/t18-/m0/s1

SMILES Code

OC1=CC2=C([C@H](CC3=C4C=CC=CC4=CC=C3)NCC2)C=C1O

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

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 305.38 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: Park SI, Kim J, Yu KS, Jang IJ, Lee S. Changes in Cardiac Function After a Single Intravenous Administration of CKD-712 in Healthy Male Volunteers. Clin Drug Investig. 2017 Feb 3. doi: 10.1007/s40261-017-0494-3. [Epub ahead of print] PubMed PMID: 28160190. 2: 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. PubMed PMID: 25482101. 3: 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. PubMed PMID: 25058922. 4: 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. 5: 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. PubMed PMID: 24293010; PubMed Central PMCID: PMC3887938. 6: 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. PubMed PMID: 24021535. 7: 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. 8: Lee J, Yang EJ, Shin JS, Kim DH, Lee SS, Choi IH. CKD-712, (S)-1-(α-naphthylmethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, Inhibits the NF-κB Activation and Augments Akt Activation during TLR4 Signaling. Immune Netw. 2011 Dec;11(6):420-3. doi: 10.4110/in.2011.11.6.420. PubMed PMID: 22346785; PubMed Central PMCID: PMC3275714. 9: 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. PubMed PMID: 21547682. 10: 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. 11: 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. PubMed PMID: 21457762. 12: 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. PubMed PMID: 19540498. 13: 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. PubMed PMID: 19458286. 14: 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. PubMed PMID: 18634870. 15: 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. PubMed PMID: 18262205. 16: 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. PubMed PMID: 17020781. 17: 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. 18: 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. 19: 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. 20: 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.

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