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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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Luke Gammon et al.
PloS one, 8(4), e62493-e62493 (2013-05-03)
The glycolytic response of hypoxic cells is primarily mediated by the hypoxia inducible factor alpha (HIF-1α) but even in the presence of abundant oxygen tumours typically show high rates of glycolysis. Higher levels of HIF-1α in tumours are associated with
Jian Kong et al.
PloS one, 7(5), e37266-e37266 (2012-05-23)
The mechanism of rapid growth of the residual tumor after radiofrequency (RF) ablation is poorly understood. In this study, we investigated the effect of hyperthermia on HepG2 cells and generated a subline with enhanced viability and dys-regulated angiogenesis in vivo
Kota Wakiyama et al.
Scientific reports, 7(1), 12653-12653 (2017-10-06)
This study aimed to establish a therapeutic strategy targeting hypoxic cancer cells in gastric carcinoma (GC). YC-1 is a HIF-1α inhibitor, and we revealed that low-dose YC-1 (10 µM) suppressed HIF-1α expression, and induced hypoxia-dependent apoptosis in the GC cell line
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
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)
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Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

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