Lificiguat

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

MedKoo CAT#: 406116

CAS#: 170632-47-0

Description: Lificiguat, also known as YC-1, is a inhibitor of Hypoxia-inducible factor-1alpha (HIF-1alpha). YC-1 is widely used as a potent inhibitor of HIF-1alpha both in vitro and in vivo, and is also being developed as a novel anticancer drug. YC-1 effectively inhibits tumor invasion and metastasis, and imply that YC-1 is worth while to further develop as a multipurpose anticancer drug.


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10mg
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100mg
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1g
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25mg
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200mg
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2g
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50mg
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500mg
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5g
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Lificiguat is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 406116
Name: Lificiguat
CAS#: 170632-47-0
Chemical Formula: C19H16N2O2
Exact Mass: 304.12118
Molecular Weight: 304.34
Elemental Analysis: C, 74.98; H, 5.30; N, 9.20; O, 10.51


Synonym: YC1; YC 1; YC-1; Lificiguat.

IUPAC/Chemical Name: 5-​[1-​(phenylmethyl)-​1H-​indazol-​3-​yl]-​2-​furanmethanol

InChi Key: OQQVFCKUDYMWGV-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H16N2O2/c22-13-15-10-11-18(23-15)19-16-8-4-5-9-17(16)21(20-19)12-14-6-2-1-3-7-14/h1-11,22H,12-13H2

SMILES Code: OCC1=CC=C(C2=NN(CC3=CC=CC=C3)C4=C2C=CC=C4)O1


Technical Data

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).

Harmonized System Code:
293490


Additional Information

  
 
 
 


References

1: Tsui L, Fong TH, Wang IJ. The effect of 3-(5'-hydroxymethyl-2'-furyl)-1-benzylindazole (YC-1) on cell viability under hypoxia. Mol Vis. 2013 Nov 16;19:2260-73. eCollection 2013. PubMed PMID: 24265542; PubMed Central PMCID: PMC3834593.

2: Carroll CE, Liang Y, Benakanakere I, Besch-Williford C, Hyder SM. The anticancer agent YC-1 suppresses progestin-stimulated VEGF in breast cancer cells and arrests breast tumor development. Int J Oncol. 2013 Jan;42(1):179-87. doi: 10.3892/ijo.2012.1675. Epub 2012 Oct 24. PubMed PMID: 23123638; PubMed Central PMCID: PMC3583650.

3: Tsui L, Fong TH, Wang IJ. YC-1 targeting of hypoxia-inducible factor-1α reduces RGC-5 cell viability and inhibits cell proliferation. Mol Vis. 2012;18:1594-603. Epub 2012 Jun 15. PubMed PMID: 22736948; PubMed Central PMCID: PMC3380911.

4: Cheng Y, Li W, Liu Y, Cheng HC, Ma J, Qiu L. YC-1 exerts inhibitory effects on MDA-MB-468 breast cancer cells by targeting EGFR in vitro and in vivo under normoxic condition. Chin J Cancer. 2012 May;31(5):248-56. doi: 10.5732/cjc.011.10383. Epub 2012 Apr 13. PubMed PMID: 22507221; PubMed Central PMCID: PMC3777523.

5: Yan J, Zhou B, Taheri S, Shi H. Differential effects of HIF-1 inhibition by YC-1 on the overall outcome and blood-brain barrier damage in a rat model of ischemic stroke. PLoS One. 2011;6(11):e27798. doi: 10.1371/journal.pone.0027798. Epub 2011 Nov 16. PubMed PMID: 22110762; PubMed Central PMCID: PMC3218033.

6: Li Y, Zhao X, Tang H, Zhong Z, Zhang L, Xu R, Li S, Wang Y. Effects of YC-1 on hypoxia-inducible factor 1 alpha in hypoxic human bladder transitional carcinoma cell line T24 cells. Urol Int. 2012;88(1):95-101. doi: 10.1159/000331881. Epub 2011 Oct 25. PubMed PMID: 22041818.

7: Liu H, Li M, Wang P, Wang F. Blockade of hypoxia-inducible factor-1α by YC-1 attenuates interferon-γ and tumor necrosis factor-α-induced intestinal epithelial barrier dysfunction. Cytokine. 2011 Dec;56(3):581-8. doi: 10.1016/j.cyto.2011.08.023. Epub 2011 Sep 3. PubMed PMID: 21890376.

8: Feng Y, Zhu H, Ling T, Hao B, Zhang G, Shi R. Effects of YC-1 targeting hypoxia-inducible factor 1 alpha in oesophageal squamous carcinoma cell line Eca109 cells. Cell Biol Int. 2011 May;35(5):491-7. doi: 10.1042/CBI20090419. PubMed PMID: 20977428.

9: DeNiro M, Al-Halafi A, Al-Mohanna FH, Alsmadi O, Al-Mohanna FA. Pleiotropic effects of YC-1 selectively inhibit pathological retinal neovascularization and promote physiological revascularization in a mouse model of oxygen-induced retinopathy. Mol Pharmacol. 2010 Mar;77(3):348-67. doi: 10.1124/mol.109.061366. Epub 2009 Dec 14. PubMed PMID: 20008515.

10: Moon SY, Chang HW, Roh JL, Kim GC, Choi SH, Lee SW, Cho KJ, Nam SY, Kim SY. Using YC-1 to overcome the radioresistance of hypoxic cancer cells. Oral Oncol. 2009 Oct;45(10):915-9. doi: 10.1016/j.oraloncology.2009.04.005. Epub 2009 May 19. PubMed PMID: 19457706.

11: Wang SX, Pei ZZ, Wu XH, Li JK, Yang YJ. [Effect of YC-1 on HIF-1 alpha and VEGF expression in human hepatocarcinoma cell lines]. Zhonghua Gan Zang Bing Za Zhi. 2009 Apr;17(4):308-9. Chinese. PubMed PMID: 19403034.

12: Li SH, Shin DH, Chun YS, Lee MK, Kim MS, Park JW. A novel mode of action of YC-1 in HIF inhibition: stimulation of FIH-dependent p300 dissociation from HIF-1{alpha}. Mol Cancer Ther. 2008 Dec;7(12):3729-38. doi: 10.1158/1535-7163.MCT-08-0074. PubMed PMID: 19074848.

13: Song SJ, Chung H, Yu HG. Inhibitory effect of YC-1, 3-(5'-hydroxymethyl-2'-furyl)-1-benzylindazole, on experimental choroidal neovascularization in rat. Ophthalmic Res. 2008;40(1):35-40. Epub 2007 Nov 20. PubMed PMID: 18032914.

14: Yeh WL, Lu DY, Lin CJ, Liou HC, Fu WM. Inhibition of hypoxia-induced increase of blood-brain barrier permeability by YC-1 through the antagonism of HIF-1alpha accumulation and VEGF expression. Mol Pharmacol. 2007 Aug;72(2):440-9. Epub 2007 May 18. PubMed PMID: 17513385.

15: Shin DH, Kim JH, Jung YJ, Kim KE, Jeong JM, Chun YS, Park JW. Preclinical evaluation of YC-1, a HIF inhibitor, for the prevention of tumor spreading. Cancer Lett. 2007 Sep 18;255(1):107-16. Epub 2007 May 14. PubMed PMID: 17502124.

16: Zhao Q, Du J, Gu H, Teng X, Zhang Q, Qin H, Liu N. Effects of YC-1 on hypoxia-inducible factor 1-driven transcription activity, cell proliferative vitality, and apoptosis in hypoxic human pancreatic cancer cells. Pancreas. 2007 Mar;34(2):242-7. PubMed PMID: 17312464.

17: Sun HL, Liu YN, Huang YT, Pan SL, Huang DY, Guh JH, Lee FY, Kuo SC, Teng CM. YC-1 inhibits HIF-1 expression in prostate cancer cells: contribution of Akt/NF-kappaB signaling to HIF-1alpha accumulation during hypoxia. Oncogene. 2007 Jun 7;26(27):3941-51. Epub 2007 Jan 8. PubMed PMID: 17213816.

18: Du J, Zhao Q, Gu H, Teng XL, Qin H, Liu NZ. [Inhibitory effect of YC-1 on induction of VEGF and GPI genes in hypoxic human pancreatic cancer cells]. Zhonghua Zhong Liu Za Zhi. 2006 Jul;28(7):486-9. Chinese. PubMed PMID: 17147109.

19: Lau CK, Yang ZF, Lam CT, Tam KH, Poon RT, Fan ST. Suppression of hypoxia inducible factor-1alpha (HIF-1alpha) by YC-1 is dependent on murine double minute 2 (Mdm2). Biochem Biophys Res Commun. 2006 Oct 6;348(4):1443-8. Epub 2006 Aug 11. PubMed PMID: 16919599.

20: Yeo EJ, Ryu JH, Chun YS, Cho YS, Jang IJ, Cho H, Kim J, Kim MS, Park JW. YC-1 induces S cell cycle arrest and apoptosis by activating checkpoint kinases. Cancer Res. 2006 Jun 15;66(12):6345-52. PubMed PMID: 16778212.