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Y102

Sigma-Aldrich

YC-1

powder

Synonym(s):

3-(5′-Hydroxymethyl-2′-furyl)-1-benzyl indazole

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About This Item

Empirical Formula (Hill Notation):
C19H16N2O2
CAS Number:
170632-47-0
Molecular Weight:
304.34
MDL number:
MFCD06407798
UNSPSC Code:
41106305
PubChem Substance ID:
24278782
NACRES:
NA.77

form

powder

Quality Level

200

color

white to yellow

solubility

DMSO: 10 mg/mL
H2O: insoluble

SMILES string

OCc1ccc(o1)-c2nn(Cc3ccccc3)c4ccccc24

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

InChI key

OQQVFCKUDYMWGV-UHFFFAOYSA-N

Gene Information

human ... PDE5A(8654)

Application

YC-1 has been used as a hypoxia-inducible factor 1α (HIF-1α) inhibitor:
  • to reduce hypoxia induced Jagged1 expression in cardiomyocytes (CMs)
  • to study its effect on progenitor expansion and CD34+ and side population (SP) cell phenotype and on the proliferation rate of cells with an ability to form long term colony forming units
  • to study its effect on regulating sphingosine 1-phosphate (S1P) bound to albumin induced plasminogen activator inhibitor 1 (PAI-1) expression by activating Rho/ Rho-associated protein kinase (ROCK) pathway.

Biochem/physiol Actions

NO (nitric oxide)-independent activator of soluble guanylyl cyclase.
YC-1 activates soluble guanylyl cyclase and prevents platelet aggregation and vascular contraction. It has a potential to treat circulation disorders. YC-1 also has an ability to inhibit hypoxia-inducible factor 1α (HIF-1α) activity in vitro. It acts as a potential antiangiogenic anticancer agent.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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YC-1: a potential anticancer drug targeting hypoxia-inducible factor 1
Yeo EJ, et al.
Journal of the National Cancer Institute, 95(7), 516-525 (2003)
Zong-Tao Chai et al.
PloS one, 8(10), e77957-e77957 (2013-11-07)
microRNAs (miRNAs) have been reported to regulate angiogenesis by down-regulating the expression of pro-angiogenic or anti-angiogenic factors. The aims of this study were to investigate whether miR-26a inhibited angiogenesis by down-regulating vascular endothelial growth factor A (VEGFA) and its clinical
Hypoxia-stressed cardiomyocytes promote early cardiac differentiation of cardiac stem cells through HIF-1$\alpha$/Jagged1/Notch1 signaling
Wang K, et al.
Acta Pharmaceutica Sinica. B, 8(5), 795-804 (2018)
Vehicle-dependent effects of sphingosine 1-phosphate on plasminogen activator inhibitor-1 expression
Takahashi C, et al.
Journal of Atherosclerosis and Thrombosis, 37663-37663 (2017)
F N Ko et al.
Blood, 84(12), 4226-4233 (1994-12-15)
YC-1 [3-(5'-hydroxymethyl-2'-furyl)-1-benzylindazole] inhibited the aggregation of and ATP release from washed rabbit platelets induced by arachidonic acid (AA), collagen, U46619, platelet-activating factor (PAF), and thrombin in a concentration-dependent manner. YC-1 also disaggregated the clumped platelets caused by these inducers. The
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