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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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500 ML
CN¥546.78

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500 ML
CN¥546.78

About This Item

Empirical Formula (Hill Notation):
C14H21N3O · 2HCl
CAS Number:
129830-38-2
Molecular Weight:
320.26
MDL number:
MFCD03490488
UNSPSC Code:
12352200
PubChem Substance ID:
24277699
NACRES:
NA.77

CN¥546.78

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biological source

synthetic (organic)

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

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Quality Level

200

Quality Level

300

Quality Level

200

Quality Level

300

solubility

water: soluble

solubility

water: soluble

solubility

water: soluble

solubility

water: soluble

form

lyophilized powder

form

lyophilized powder

form

lyophilized powder

form

lyophilized powder

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

color

white to light yellow

color

off-white to faint yellow

color

white to yellow cast

color

white to faint yellow

General description

Y-27632 dihydrochloride is an effective bronchodilator and improves lung resistance (RL) induced by antigen and acetylcholine.[1] Y-27632 controls neutrophil migration and lung edema and may be a potential agent against acute lung injury.[2]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[3]
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.[4] 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.[5] 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.[6] Ki = 140 nM for p160ROCK.

Application

Y-27632 dihydrochloride has been used:
  • as a medium supplement in pancreatic ductal adenocarcinoma organoid culture[7]
  • in the inhibition of Ras homolog gene family (Rho) kinase in mouse embryonic stem cells[8]
  • in the inhibition of Rho-associated protein kinase (ROCK) in human embryonic stem cells[9] and human induced pluripotent stem cells (iPSCs)[10]
  • Y-27632 dihydrochloride has been used as a supplement in the E8 medium to promote in vitro differentiation of human pluripotent stem cells[11]

Biochem/physiol Actions

Y-27632 is a highly potent, cell-permeable, selective ROCK inhibitor.
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
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    Certificates of Analysis (COA)

    Lot/Batch Number
    0000435350
    0000435350
    0000393704
    0000393704
    0000395536

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    Y-27632, an inhibitor of Rho-kinase, antagonizes noradrenergic contractions in the rabbit and human penile corpus cavernosum
    Rees RW, et al.
    Br. J. Pharmacol. (Proceed. Suppl.), 133, 455-458 (2001)
    Y-27632, an inhibitor of Rho-kinase, antagonizes noradrenergic contractions in the rabbit and human penile corpus cavernosum
    Rees RW, et al.
    British Journal of Pharmacology, 133, 455-458 (2001)
    Taisuke Kadoshima et al.
    Proceedings of the National Academy of Sciences of the United States of America, 110(50), 20284-20289 (2013-11-28)
    Here, using further optimized 3D culture that allows highly selective induction and long-term growth of human ES cell (hESC)-derived cortical neuroepithelium, we demonstrate unique aspects of self-organization in human neocorticogenesis. Self-organized cortical tissue spontaneously forms a polarity along the dorsocaudal-ventrorostral
    Evaluation of Y-27632, a rho-kinase inhibitor, as a bronchodilator in guinea pigs
    Iizuka K, et al.
    European Journal of Pharmacology, 406(2), 273-279 (2000)
    Basement membrane destruction by pancreatic stellate cells leads to local invasion in pancreatic ductal adenocarcinoma
    Koikawa K, et al.
    Cancer Letters, 425, 65-77 (2018)
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