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SML2589

Sigma-Aldrich

Dasatinib

≥98% (HPLC)

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Synonym(s):
BMS 354825, BMS-354825, BMS354825, N-(2-Chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazolecarboxamide
Empirical Formula (Hill Notation):
C22H26ClN7O2S
CAS Number:
302962-49-8
Molecular Weight:
488.01
MDL number:
MFCD11046566
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

CC1=NC(NC2=NC=C(C(NC3=C(C=CC=C3Cl)C)=O)S2)=CC(N4CCN(CC4)CCO)=N1

InChI

1S/C22H26ClN7O2S/c1-14-4-3-5-16(23)20(14)28-21(32)17-13-24-22(33-17)27-18-12-19(26-15(2)25-18)30-8-6-29(7-9-30)10-11-31/h3-5,12-13,31H,6-11H2,1-2H3,(H,28,32)(H,24,25,26,27)

InChI key

ZBNZXTGUTAYRHI-UHFFFAOYSA-N

Gene Information

human ... ABL1(25) , BLK(640) , EPHA2(1969) , FGR(2268) , FRK(2444) , FYN(2534) , HCK(3055) , KIT(3815) , LCK(3932) , LYN(4067) , PDGFRB(5159) , SRC(6714) , SRMS(6725) , YES1(7525)

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Application

Dasatinib has been used:
  • as a protein kinase inhibitor to study its effects on macrophage polarization, lipogenesis, western diet-induced progression of simple steatosis into steatohepatitis (NASH), and liver fibrosis in mice
  • as an SRC tyrosine kinase inhibitor to study its effects on hepatocellular carcinoma cells
  • as a tyrosine kinase inhibitor to study its effects on autophagy in neuronal cells

Biochem/physiol Actions

Dasatinib is a thiazole-carboxamide compound that inhibits a broad spectrum of protein kinases such as breakpoint cluster region-tyrosine protein kinase ABL (Bcr-Abl), Btk family members, platelet-derived growth factor receptor α/β (PDGFR-α/β), and ephrin receptor kinase. It also inhibits Src-family kinases such as SRC tyrosine kinase, and lymphocyte-specific protein kinase (LCK). Dasatinib exhibits certain effects on hematopoietic cells like suppressing natural killer cell toxicity, inhibiting T lymphocytes activation and proliferation, and influencing platelet activation. It is also studied in the treatment of chronic myeloid leukemia (CML) and acute lymphoblastic leukemia (ALL).

Signal Word

Danger

Hazard Classifications

Aquatic Chronic 1 - Carc. 2 - Eye Dam. 1 - Repr. 2 - Skin Irrit. 2 - STOT RE 1

Target Organs

Gastro-intestinal system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Helena Motaln et al.
Brain : a journal of neurology, 146(10), 4088-4104 (2023-04-19)
Nuclear to cytoplasmic mislocalization and aggregation of multiple RNA-binding proteins (RBPs), including FUS, are the main neuropathological features of the majority of cases of amyotrophic lateral sclerosis (ALS) and frontotemporal lobular degeneration (FTLD). In ALS-FUS, these aggregates arise from disease-associated
Liat Bar-On et al.
PloS one, 18(12), e0294176-e0294176 (2023-12-27)
SARS-CoV-2 infection elicits robust CD8 T-cell responses, yet the identity of the mechanisms playing dominant roles in initiating the virus-specific CD8 T-cell responses are largely unknown. In the present study, we interrogate the contribution of the cDC1 subset to SARS-CoV-2-specific
Khushwant S Bhullar et al.
Food chemistry. Molecular sciences, 4, 100069-100069 (2022-04-14)
Dasatinib, a small-molecule drug used as a treatment for chronic myeloid leukemia induces mitochondrial damage in embryonic kidney (293 T) cells (p < 0.05). This dasatinib induced mitochondrial injury in kidney cells was mitigated by H3K36me3 activating ovotransferrin-derived peptides GWN and GW. Pre-treatment
Hassan Reda Hassan Elsayed et al.
Annals of anatomy = Anatomischer Anzeiger : official organ of the Anatomische Gesellschaft, 234, 151626-151626 (2020-11-05)
Non-alcoholic fatty liver disease (NAFLD) is a worldwide disease that progresses into steatohepatitis (NASH) that has no current effective treatment. This study aimed, for the first time, to investigate the effect of Dasatinib; a tyrosine kinase inhibitor showing anti-PDGFR activity
Amélie Marguier et al.
Frontiers in immunology, 13, 932298-932298 (2022-08-09)
Myeloid-derived suppressor cells (MDSCs) are a heterogeneous group of immune suppressive cells detected in several human cancers. In this study, we investigated the features and immune suppressive function of a novel subset of monocytic MDSC overexpressing TIE-2 (TIE-2+ M-MDSC), the
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