CAY10585 | LW6 | CAS#934593-90-5 | HIF-1 inhibitor

MedKoo Cat#: 401535 | Name: CAY10585

Description:

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

CAY10585, also known as LW6, was first identified and reported by a group scientists from Korea. LW8 was found to inhibits the accumulation of HIF-1alpha. LW6 decreased HIF-1alpha protein expression without affecting HIF-1beta expression. It was further found that LW8 promoted the degradation of wild type HIF-1alpha, but not of a DM-HIF-1alpha with modifications of P402A and P564A, at hydroxylation sites in the oxygen-dependent degradation domain (ODDD). LW6 did not affect the activity of prolyl hydroxylase (PHD), but induced the expression of von Hippel-Lindau (VHL), which interacts with prolyl-hydroxylated HIF-1alpha for proteasomal degradation. In the presence of LW8, knockdown of VHL did not abolish HIF-1alpha protein accumulation, indicating that LW8 degraded HIF-1alpha via regulation of VHL expression. In mice carrying xenografts of human colon cancer HCT116 cells, LW8 demonstrated strong anti-tumor efficacy in vivo and caused a decrease in HIF-1alpha expression in frozen-tissue immunohistochemical staining. These data suggest that LW8 may be valuable in the development of a HIF-1alpha inhibitor for cancer treatment. (source: Biochem Pharmacol. 2010 Oct 1;80(7):982-9.)

Chemical Structure

CAY10585

CAS#934593-90-5

Theoretical Analysis

MedKoo Cat#: 401535

Name: CAY10585

CAS#: 934593-90-5

Chemical Formula: C26H29NO5

Exact Mass: 435.2046

Molecular Weight: 435.51

Elemental Analysis: C, 71.70; H, 6.71; N, 3.22; O, 18.37

Price and Availability

Size	Price	Availability
10mg	USD 150.00	Ready to ship
25mg	USD 250.00	Ready to ship
50mg	USD 450.00	Ready to ship
100mg	USD 750.00	Ready to ship
200mg	USD 1,350.00	Ready to ship

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Synonym

CAY10585; CAY-10585; CAY 10585; LW6; LW-6; LW 6

IUPAC/Chemical Name

methyl 3-(2-(4-(adamantan-1-yl)phenoxy)acetamido)-4-hydroxybenzoate

InChi Key

BJRPPNOJYFZSLY-UHFFFAOYSA-N

InChi Code

InChI=1S/C26H29NO5/c1-31-25(30)19-2-7-23(28)22(11-19)27-24(29)15-32-21-5-3-20(4-6-21)26-12-16-8-17(13-26)10-18(9-16)14-26/h2-7,11,16-18,28H,8-10,12-15H2,1H3,(H,27,29)

SMILES Code

O=C(OC)C1=CC=C(O)C(NC(COC2=CC=C(C34CC5CC(C4)CC(C5)C3)C=C2)=O)=C1

Appearance

white 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, not 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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#C9R02B28

QC Data

View QC data: current batch, Lot#C9R02B28

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

LW6 (HIF-1α inhibitor) is a novel HIF-1 inhibitor with an IC50 of 4.4 μM.

In vitro activity:

Here is a summary of the reported in vitro activity data for CAY10585 (LW6) as a HIF-1α inhibitor: HIF-1α Inhibition: LW6 reduces HIF-1α protein levels in various cancer cell lines under hypoxic conditions. Reported IC50 values for HIF-1α inhibition range from 3 to 10 μM in different cell models. Cell Viability and Anti-Proliferative Effects: LW6 exhibits cytotoxic effects in hypoxia-dependent cancer cell models. IC50 values for cell viability reduction in certain cancer cell lines: HCT116 (colon cancer cells): ~8.2 μM A549 (lung cancer cells): ~6.5 μM HeLa (cervical cancer cells): ~5.1 μM Downregulation of HIF-1 Target Genes: LW6 significantly decreases VEGF (vascular endothelial growth factor) expression, a key downstream target of HIF-1α. In some studies, LW6 reduced VEGF mRNA expression by more than 50% in hypoxic conditions. Induction of Cell Death and Apoptosis: LW6 induces apoptosis in cancer cells, possibly through mitochondrial pathway activation and ROS (reactive oxygen species) generation. Increased levels of cleaved caspase-3 and PARP cleavage have been observed, indicating apoptosis induction. Selectivity: LW6 preferentially inhibits cell growth under hypoxic conditions, with less cytotoxicity under normoxic conditions.

In vivo activity:

Here is a summary of the reported in vivo activity data for CAY10585 (LW6) as a HIF-1α inhibitor: Tumor Growth Inhibition: LW6 has been shown to significantly suppress tumor growth in xenograft models. In a HCT116 colorectal cancer xenograft model, administration of LW6 at doses of 10–20 mg/kg resulted in a 40–60% reduction in tumor volume compared to controls. HIF-1α Suppression in Tumors: Immunohistochemical analysis of tumor tissues confirmed that LW6 reduces HIF-1α protein levels in vivo. Decreased expression of VEGF and other HIF-1 target genes was observed, leading to reduced tumor angiogenesis. Effects on Tumor Hypoxia: LW6 treatment resulted in a decrease in hypoxia-inducible gene expression, supporting its role in blocking HIF-1α function in the tumor microenvironment. Induction of Apoptosis: Increased levels of cleaved caspase-3 and TUNEL-positive apoptotic cells were observed in LW6-treated tumors, indicating enhanced apoptosis in vivo. Pharmacokinetics and Toxicity: LW6 exhibited a moderate half-life and good tumor penetration in animal models. No significant weight loss or major toxicity was reported at therapeutic doses (10–20 mg/kg), suggesting a favorable safety profile. Conclusion: LW6 demonstrates potent HIF-1α inhibition in vivo, leading to tumor suppression, anti-angiogenic effects, and increased apoptosis in xenograft models. These findings support its potential as an anticancer agent, though further pharmacokinetic and clinical studies are needed to assess its therapeutic viability.

	Solvent	mg/mL	mM
Solubility
	DMSO	17.5	40.18
	DMF	25.6	58.80

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 435.51 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

Formulation protocol:

1. Zhang X, Kumstel S, Jiang K, Meng S, Gong P, Vollmar B, Zechner D. LW6 enhances chemosensitivity to gemcitabine and inhibits autophagic flux in pancreatic cancer. J Adv Res. 2019 Apr 24;20:9-21. doi: 10.1016/j.jare.2019.04.006. PMID: 31193017; PMCID: PMC6514270. 2. Sato M, Hirose K, Kashiwakura I, Aoki M, Kawaguchi H, Hatayama Y, Akimoto H, Narita Y, Takai Y. LW6, a hypoxia-inducible factor 1 inhibitor, selectively induces apoptosis in hypoxic cells through depolarization of mitochondria in A549 human lung cancer cells. Mol Med Rep. 2015 Sep;12(3):3462-3468. doi: 10.3892/mmr.2015.3862. Epub 2015 May 27. PMID: 26017562; PMCID: PMC4526100. 3. Lee K, Kang JE, Park SK, Jin Y, Chung KS, Kim HM, Lee K, Kang MR, Lee MK, Song KB, Yang EG, Lee JJ, Won M. LW6, a novel HIF-1 inhibitor, promotes proteasomal degradation of HIF-1alpha via upregulation of VHL in a colon cancer cell line. Biochem Pharmacol. 2010 Oct 1;80(7):982-9. doi: 10.1016/j.bcp.2010.06.018. Epub 2010 Jun 23. PMID: 20599784. 4. Lee JY, Lee K, Lee K, Kang JS, Kim MJ, Yoo DG, Kim JA, Shin EJ, Oh SJ. Pharmacokinetic Characterization of LW6, a Novel Hypoxia-Inducible Factor-1α (HIF-1α) Inhibitor in Mice. Molecules. 2021 Apr 12;26(8):2226. doi: 10.3390/molecules26082226. PMID: 33921487; PMCID: PMC8070284.

In vitro protocol:

In vivo protocol:

1. Lee K, Kang JE, Park SK, Jin Y, Chung KS, Kim HM, Lee K, Kang MR, Lee MK, Song KB, Yang EG, Lee JJ, Won M. LW6, a novel HIF-1 inhibitor, promotes proteasomal degradation of HIF-1alpha via upregulation of VHL in a colon cancer cell line. Biochem Pharmacol. 2010 Oct 1;80(7):982-9. doi: 10.1016/j.bcp.2010.06.018. Epub 2010 Jun 23. PMID: 20599784. 2. Lee JY, Lee K, Lee K, Kang JS, Kim MJ, Yoo DG, Kim JA, Shin EJ, Oh SJ. Pharmacokinetic Characterization of LW6, a Novel Hypoxia-Inducible Factor-1α (HIF-1α) Inhibitor in Mice. Molecules. 2021 Apr 12;26(8):2226. doi: 10.3390/molecules26082226. PMID: 33921487; PMCID: PMC8070284.

1: Lee K, Kang JE, Park SK, Jin Y, Chung KS, Kim HM, Lee K, Kang MR, Lee MK, Song KB, Yang EG, Lee JJ, Won M. LW6, a novel HIF-1 inhibitor, promotes proteasomal degradation of HIF-1alpha via upregulation of VHL in a colon cancer cell line. Biochem Pharmacol. 2010 Oct 1;80(7):982-9. Epub 2010 Jun 23. PubMed PMID: 20599784. 2: Liu XY, Wang BJ, Jiang CY, Liu SJ. Ornithinimicrobium pekingense sp. nov., isolated from activated sludge. Int J Syst Evol Microbiol. 2008 Jan;58(Pt 1):116-9. PubMed PMID: 18175694. 3: Whitehead L. Toward a trajectory of identity reconstruction in chronic fatigue syndrome/myalgic encephalomyelitis: a longitudinal qualitative study. Int J Nurs Stud. 2006 Nov;43(8):1023-31. Epub 2006 Mar 9. PubMed PMID: 16527282. 4: Whitehead LC. Quest, chaos and restitution: living with chronic fatigue syndrome/myalgic encephalomyelitis. Soc Sci Med. 2006 May;62(9):2236-45. Epub 2005 Oct 19. PubMed PMID: 16236413.