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Key Documents

Y0503

Sigma-Aldrich

Y-27632 dihydrochloride

≥98% (HPLC)

Synonym(s):

Rock inhibitor y-27632, Y-27632 2HCl, (R)-(+)-trans-4-(1-Aminoethyl)-N-(4-Pyridyl)cyclohexanecarboxamide dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C14H21N3O · 2HCl
CAS Number:
Molecular Weight:
320.26
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +3.0 to +5.0°, c = 1.0 in methanol

color

white to beige

solubility

H2O: 14 mg/mL

storage temp.

2-8°C

SMILES string

Cl.Cl.C[C@@H](N)[C@H]1CC[C@@H](CC1)C(=O)Nc2ccncc2

InChI

1S/C14H21N3O.2ClH/c1-10(15)11-2-4-12(5-3-11)14(18)17-13-6-8-16-9-7-13;;/h6-12H,2-5,15H2,1H3,(H,16,17,18);2*1H/t10-,11-,12-;;/m1../s1

InChI key

IDDDVXIUIXWAGJ-LJDSMOQUSA-N

Gene Information

General description

Y-27632 dihydrochloride is an effective bronchodilator and improves lung resistance (RL) induced by antigen and acetylcholine. Y-27632 controls neutrophil migration and lung edema and may be a potential agent against acute lung injury.The utilization of Y-27632 dihydrochloride, in conjunction with Accutase or other enzyme solutions, during the passaging of human embryonic stem (hES) cells has been demonstrated to enhance cell survival and significantly improve cloning efficiency
Y-27632, a Rho-kinase inhibitor, counteracts noradrenergic contractions in the penile corpus cavernosum of rabbits and humans. It helps to relax vascular and non-vascular smooth muscle in various preparations and lower blood pressure in hypertensive rats. Additionally, this inhibitor induces reversible changes in cell shape and decreases in actin stress fibers, focal adhesions, and protein phosphotyrosine staining in human trabecular meshwork (TM) cells and Schlemm′s canal cells. Y-27632 inhibits the kinase activity of both ROCK-I and ROCK-II in vitro, and this inhibition is competitively reversed by ATP, indicating that these compounds bind to the catalytic site to inhibit the kinases. Ki = 140 nM for p160ROCK.

Application

Y-27632 dihydrochloride has been used:
  • as a medium supplement in pancreatic ductal adenocarcinoma organoid culture
  • in the inhibition of Ras homolog gene family (Rho) kinase in mouse embryonic stem cells
  • in the inhibition of Rho-associated protein kinase (ROCK) in human embryonic stem cells and human induced pluripotent stem cells (iPSCs)
  • Y-27632 dihydrochloride has been used as a supplement in the E8 medium to promote in vitro differentiation of human pluripotent stem cells

Biochem/physiol Actions

Y-27632 is highly potent, cell-permeable, selective ROCK (Rho-associated coiled coil forming protein serine/threonine kinase) inhibitor. Ki = 140 nM for p160ROCK. Y-27632 also inhibits ROCK-II with equal potency. The inhibition is competitive with respect to ATP.

Features and Benefits

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

Legal Information

Sold under license from Mitsubishi Pharma Corporation

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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Attenuation of endotoxin-induced acute lung injury by the Rho-associated kinase inhibitor, Y-27632
Tasaka S, et al.
American Journal of Respiratory Cell and Molecular Biology, 32(6), 504-510 (2005)
Human cardiomyocytes undergo enhanced maturation in embryonic stem cell-derived organoid transplants
Varzideh F, et al.
Biomaterials, 192, 537-550 (2018)
Xiangyun Li et al.
Human reproduction (Oxford, England), 24(3), 580-589 (2008-12-06)
Efficient slow freezing protocols within serum-free and feeder-free culture systems are crucial for the clinical application of human embryonic stem (hES) cells. Frequently, however, hES cells must be cryopreserved as clumps when using conventional slow freezing protocols, leading to lower
The Cytoskeletal Network of the Trabecular Meshwork
Tian B, et al.
Journal of Separation Science (2010)
Pharmacological properties of Y-27632, a specific inhibitor of rho-associated kinases
Ishizaki T, et al.
Molecular Pharmacology, 57, 976-983 (2000)

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