1226056-71-8

Basic information

• Product Name: Thiazovivin
• Synonyms: N-Benzyl-2-(pyrimidin-4-ylamino)thiazole-4-carboxamide;Thiazovivin;N-(Phenylmethyl)-2-(4-pyrimidinylamino)-4-thiazolecarboxamide;N-(Phenylmethyl)-2-(4-pyrimidinylamino)-4-thiazolecarboxamide Thiazovivin;Thiazovivin N-(Phenylmethyl)-2-(4-pyrimidinylamino)-4-thiazolecarboxamide;Thiazovivin, >=98%;N-Benzyl-2-(4-pyrimidinylamino)-1,3-thiazole-4-carboxamide
• CAS NO: 1226056-71-8
• Molecular Formula: C₁₅H₁₃N₅OS
• Molecular Weight: 311.36162
• EINECS: 1312995-182-4
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;Inhibitors
• Mol File: 1226056-71-8.mol
• Article Data: 3

Chemical Properties

• Appearance: , white to beige to brown/
• Density: 1.379
• Storage Temp.: Store at -20°C
• Solubility: DMSO: soluble20mg/mL, clear
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months.
• CAS DataBase Reference: Thiazovivin(CAS DataBase Reference)
• NIST Chemistry Reference: Thiazovivin(1226056-71-8)
• EPA Substance Registry System: Thiazovivin(1226056-71-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 1226056-71-8(Hazardous Substances Data)

Usage

Description

Different sources of media describe the Description of 1226056-71-8 differently. You can refer to the following data:
1. Thiazovivin is a novel ROCK inhibitor with IC50 of 0.5 μM in a cell-free assay, promotes hESC survival after single-cell dissociation.
2. Thiazovivin (1226056-71-8) dramatically improves (200-fold) the efficiency of induced pluripotent stem cell generation from human fibroblasts.1 Induces direct conversion of porcine embryonic fibroblasts into adipocytes.2?Cell permeable.

In vitro

Although displaying little impact on cell proliferation, Thiazovivin treatment significantly enhances the survival of human embryonic stem cells (hESCs) after enzymatic dissociation more than 30-fold, while homogenously maintaining pluripotency with the characteristic colony morphology, expression of typical pluripotency markers such as alkaline phosphatase (ALP), and normal karyotype. Dissociated hESCs treated with Thiazovivin display dramatically increased adhesion to matrigel-or laminin-coated plates but not to gelatin-coated plates within a few hours. Thiazovivin treatment increases cell-ECM adhesion-mediated β1 integrin activity, which synergizes with growth factors to promote cell survival. In addition to activating integrin, Thiazovivin but not Tyrintegin (Ptn) protects hESCs from death in the absence of ECM in suspension through E-cadherin-mediated cell-cell interaction. Thiazovivin treatment potently inhibits endocytosis of E-cadherin, consequently stabilizing E-cadherin on the cell surface and leading to reestablishment of cell-cell interaction, which is essential for hESC survival in ECM-free conditions. Thiazovivin but not Tyrintegin (Ptn) at 2 μM inhibits Rho-associated kinase (ROCK) activity and protects hESCs at a similar level as the widely used selective ROCK inhibitor Y-27632 at 10 μM, suggesting that Rho-ROCK signaling regulates cell-ECM and cell-cell adhesion. [1] Thiazovivin at 1 μM increases the reprogramming efficiency of CB mononuclear cells to induced pluripotent stem cells (iPSCs) by more than 10 times.

Uses

Different sources of media describe the Uses of 1226056-71-8 differently. You can refer to the following data:
1. A compound that improves the survival of human embryonic stem cells (hESCs) upon trypsinization. In combination with ALK5 (TGFβ receptor) inhibitor SB-431542 and MEK inhibitor PD-0325901 (P217450), Thiazovivin promotes the transformation of fibroblasts into stem cells with a 200-fold efficiency over the classic method
2. Thiazovivin has been used in the generation of induced pluripotent stem cells (iPSCs) and induced neural stem cells (iNSCs) from human urine cells. It has also been used to study the the effect of pro-fibrotic inhibition on cardiac reprogramming.

Biochem/physiol Actions

Thiazovivin is an inhibitor of Rho associated coiled-coil containing protein kinase (ROCK). In vitro studies prove that thiazovivin is efficient in stimulating better morphology, expression of ionic transporter and protein involved in cell adhesion.

References

1) Lin et al. (2009), A chemical platform for improved induction of iPSC; Nature Methods, 6 805 2) Zhu et al. (2012), Direct conversion of porcine embryonic fibroblasts into adipocytes by chemical molecules; Cell Reprogram., 14 99

Upstream product

• 163133-86-6 pyrimidin-4-amine 
• 1449218-23-8 N-benzyl-2-bromothiazol-4-carboxamide 

Relevant articles and documents

Ionic liquid and method for synthesizing Thiazovivin by same

The invention provides ionic liquid for synthesizing Thiazovivin, and belongs to the technical field of organic synthesis. The ionic liquid is of a structure as shown in the general formula 1. The invention further provides a Thiazovivin synthesizing method based on the ionic liquid. The Thiazovivin synthesizing method includes (1), connecting the ionic liquid to benzylamine to obtain a compound 4; (2), subjecting the compound 4 and 2-bromine thiazole-4-carboxylic acid to acylation reaction to obtain a compound 5; (3), subjecting the compound 5 and 4-aminopyrimidine to amination reaction to obtain a compound 6; (4), removing the ionic liquid in the compound 6 to obtain the Thiazovivin.

STEM CELL CULTURES

The present invention relates compounds for stabilizing cells and methods of their use.