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

Thiazovivin is a novel ROCK inhibitor with an IC50 of 0.5 μM in a cell-free assay, known for its ability to promote the survival of human embryonic stem cells (hESCs) after single-cell dissociation. It is characterized by its cell permeability and has shown significant improvements in the efficiency of induced pluripotent stem cell generation from human fibroblasts.

Uses

Used in Stem Cell Research:
Thiazovivin is used as a reagent for improving the survival of hESCs upon trypsinization, enhancing the efficiency of stem cell research and development.
Used in Cardiac Reprogramming:
Thiazovivin is used as a tool to study the effect of pro-fibrotic inhibition on cardiac reprogramming, potentially contributing to the advancement of regenerative medicine and treatment of heart-related conditions.
Used in Induced Pluripotent Stem Cell (iPSC) Generation:
Thiazovivin is used as a ROCK inhibitor to increase the efficiency of iPSC generation from human fibroblasts by 200-fold, compared to the classic method. This application aids in the development of personalized medicine and the study of various diseases using patient-specific stem cells.
Used in Induced Neural Stem Cell (iNSC) Generation:
Thiazovivin is used in the generation of iNSCs from human urine cells, providing a non-invasive method for obtaining stem cells and contributing to the understanding of neurological disorders and potential treatments.
Used in Direct Conversion of Cells:
Thiazovivin is used to induce the direct conversion of porcine embryonic fibroblasts into adipocytes, which can be applied in the study of cell differentiation and the development of therapies for obesity and related metabolic disorders.

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.

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.