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934593-90-5

934593-90-5 structure
934593-90-5 structure
  • Name: LW 6
  • Chemical Name: methyl 3-[[2-[4-(2-adamantyl)phenoxy]acetyl]amino]-4-hydroxybenzoate
  • CAS Number: 934593-90-5
  • Molecular Formula: C26H29NO5
  • Molecular Weight: 435.512
  • Catalog: Signaling Pathways Metabolic Enzyme/Protease HIF/HIF Prolyl-Hydroxylase
  • Create Date: 2017-11-20 07:50:42
  • Modify Date: 2024-01-05 17:34:27
  • LW6 is a novel HIF-1 inhibitor with an IC50 of 4.4 μM.
Name methyl 3-[[2-[4-(2-adamantyl)phenoxy]acetyl]amino]-4-hydroxybenzoate
Synonyms Hypoxia Inducible Factor-1alpha Inhibitor
methyl 4-hydroxy-3-({[4-(tricyclo[3.3.1.1]dec-1-yl)phenoxy]acetyl}amino)benzoate
Benzoic acid, 4-hydroxy-3-[[2-(4-tricyclo[3.3.1.1]dec-1-ylphenoxy)acetyl]amino]-, methyl ester
Methyl 3-[({4-[(3s,5s,7s)-adamantan-1-yl]phenoxy}acetyl)amino]-4-hydroxybenzoate
Methyl 3-({[4-(adamantan-1-yl)phenoxy]acetyl}amino)-4-hydroxybenzoate
CAY10585
LW6
Description LW6 is a novel HIF-1 inhibitor with an IC50 of 4.4 μM.
Related Catalog
Target

IC50: 4.4 μM (HIF-1)[1]

In Vitro LW6 decreases HIF-1α protein expression without affecting HIF-1β expression. LW6 affects the stability of the HIF-1α protein. LW6 promotes the degradation of wild type HIF-1α, but not of a DM-HIF-1α with modifications of P402A and P564A, at hydroxylation sites in the oxygen-dependent degradation domain. LW6 induces the expression of von Hippel-Lindau (VHL), which interacts with prolyl-hydroxylated HIF-1α for proteasomal degradation. In the presence of LW6, knockdown of VHL does not abolish HIF-1α protein accumulation, indicating that LW6 degraded HIF-1α via regulation of VHL expression[2]. In MDCKII-BCRP cells overexpressing BCRP, LW6 enhances significantly the cellular accumulation of mitoxantrone, a BCRP substrate. LW6 also down-regulates BCRP expression at concentrations of 0.1-10 µM[3]. LW6 inhibits the expression of HIF 1α induced by hypoxia in A549 cells at 20 mM, independently of the von Hippel Lindau protein. LW6 induces hypoxia selective apoptosis together with a reduction in the mitochondrial membrane potential[4].
In Vivo In mice carrying xenografts of human colon cancer HCT116 cells, LW6 demonstrates strong anti-tumor efficacy in vivo and causes a decrease in HIF-1α expression in frozen-tissue immunohistochemical staining[2].
Cell Assay Inhibition of HIF-1a is assayed by a reporter assay using dualluciferase reporter assay system. HCT116 cells in 75-90% confluence are transiently co-transfected with pGL3-HRE-luciferase plasmid containing six copies of HREs from human VEGF genes and pRLSV40 encoding firefly renilla luciferase and incubated for 24 h. Cells are treated with LW6 or 17-AAG for 16 h before report assay. Luciferase activity is integrated over a 10 second period and measured using a luminometer[2].
Animal Admin Mice: The mice receive the following treatments using a dosing vehicle solution, containing 10% dimethylacetamide, 10% Cremophor EL and 80% of sodium carbonate buffer (pH 10), by intraperitoneal (i.p.) injection: group1(control group; six mice), vehicle solution; group2 (six mice), LW6 at a dose of 10 and 20mg/kg (QD); and group 3 (six mice), topotecan at a dose of 2mg/kg, (Q2D), which is the dose and dosing schedule that showed more than 60% inhibition of growth of HCT116 tumors. The treatments are continued for 13 days[2].
References

[1]. Naik R, et al. Synthesis and structure-activity relationship study of chemical probes as hypoxia induced factor-1α/malate dehydrogenase 2 inhibitors. J Med Chem. 2014 Nov 26;57(22):9522-38.

[2]. Lee K, et al. 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.

[3]. Song JG, et al. Discovery of LW6 as a new potent inhibitor of breast cancer resistance protein.

[4]. Sato M, et al. 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):3462-8.
Density 1.3±0.1 g/cm3
Boiling Point 647.4±55.0 °C at 760 mmHg
Molecular Formula C26H29NO5
Molecular Weight 435.512
Flash Point 345.3±31.5 °C
Exact Mass 435.204559
PSA 88.35000
LogP 6.49
Vapour Pressure 0.0±2.0 mmHg at 25°C
Index of Refraction 1.637
HS Code 2924299090
52804-26-9 structure

52804-26-9

536-25-4 structure

536-25-4

~84%

934593-90-5 structure

934593-90-5

Literature: DONGGUK UNIVERSITY INDUSTRY-ACADEMIC COOPERATION FOUNDATION; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; Lee, Kyeong; Won, Mi Sun; Kim, Hwan Mook; Park, Song Kyu; Lee, Kiho; Lee, Ki Hoon; Lee, Chang Woo; Lee, Jung Joon; Chung, Kyung Sook; Kim, Bo Kyung; Jin, Yinglan; Lee, Seung-hee Patent: US2013/237542 A1, 2013 ; Location in patent: Paragraph 0216; 0217; 0218 ;
536-25-4 structure

536-25-4

~86%

934593-90-5 structure

934593-90-5

Literature: KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY Patent: WO2008/4798 A1, 2008 ; Location in patent: Page/Page column 30 ;
29799-07-3 structure

29799-07-3

~%

934593-90-5 structure

934593-90-5

Literature: Lee, Kyeong; Lee, Jeong Hyung; Boovanahalli, Shanthaveerappa K.; Jin, Yinglan; Lee, Mijeoung; Jin, Xuejun; Kim, Jin Hwan; Hong, Young-Soo; Lee, Jung Joon Journal of Medicinal Chemistry, 2007 , vol. 50, # 7 p. 1675 - 1684
52804-25-8 structure

52804-25-8

~%

934593-90-5 structure

934593-90-5

Literature: Lee, Kyeong; Lee, Jeong Hyung; Boovanahalli, Shanthaveerappa K.; Jin, Yinglan; Lee, Mijeoung; Jin, Xuejun; Kim, Jin Hwan; Hong, Young-Soo; Lee, Jung Joon Journal of Medicinal Chemistry, 2007 , vol. 50, # 7 p. 1675 - 1684
99-42-3 structure

99-42-3

~%

934593-90-5 structure

934593-90-5

Literature: Nakamura, Hiroyuki; Yasui, Yuka; Ban, Hyun Seung Journal of Organometallic Chemistry, 2013 , vol. 747, p. 189 - 194
1205117-27-6 structure

1205117-27-6

536-25-4 structure

536-25-4

~%

934593-90-5 structure

934593-90-5

Literature: Korea Research Institute of Bioscience and Biotechnology; Dongguk University Industry-Academic Cooperation Foundation; WON, Mi-Sun; KIM, Hwan-Mook; LEE, Kyeong; PARK, Song-Kyu; LEE, Ki-Ho; LEE, Chang-Woo; LEE, Jung-Joon; CHUNG, Kyung-Sook; KIM, Bo-Kyung; JIN, Ying-Lan Patent: WO2012/53768 A2, 2012 ; Location in patent: Page/Page column 14-15 ;
616-82-0 structure

616-82-0

~%

934593-90-5 structure

934593-90-5

Literature: Nakamura, Hiroyuki; Yasui, Yuka; Ban, Hyun Seung Journal of Organometallic Chemistry, 2013 , vol. 747, p. 189 - 194
HS Code 2924299090
Summary 2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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