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T6575

Sigma-Aldrich

TOFA

≥98% (HPLC)

Sinônimo(s):

5-(Tetradecyloxy)-2-furoic acid

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About This Item

Fórmula empírica (Notação de Hill):
C19H32O4
Número CAS:
54857-86-2
Peso molecular:
324.45
Número MDL:
MFCD01726059
Código UNSPSC:
12352200
ID de substância PubChem:
329826849
NACRES:
NA.77

Ensaio

≥98% (HPLC)

Formulário

powder

cor

white to beige

pf

112-115 °C

solubilidade

DMSO: 2 mg/mL, clear

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

CCCCCCCCCCCCCCOc1ccc(o1)C(O)=O

InChI

1S/C19H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-22-18-15-14-17(23-18)19(20)21/h14-15H,2-13,16H2,1H3,(H,20,21)

chave InChI

CZRCFAOMWRAFIC-UHFFFAOYSA-N

Aplicação

TOFA has been used as a lipid biosynthesis inhibitor in mesenchymal stromal cells (MSCs), human pluripotent stem cells., an acetyl-CoA carboxylase 1 inhibitor in murine adipocyte cell lines., a lipolysis inhibitor in cancer stem cells (CSCs).
TOFA has been used as an ACC inhibitor to study its effect on insulin secretion in INS-1E cells.

Ações bioquímicas/fisiológicas

5-(Tetradecyloxy)-2-furoic acid (TOFA) elicits hypolipidemic functionality by favoring fatty acid breakdown and at the same time preventing biosynthesis. It induces apoptosis in pancreatic cancer cells and favors tumor suppression.
Studies have reported that TOFA can inhibit the anorectic effect of subcutaneous tamoxifen (TMX) on food intake during refeeding experiments in rats.
TOFA is a cell-permeable, potent, reversible, and competitive inhibitor of acetyl-CoA carboxylase (ACC).
TOFA is a cell-permeable, potent, reversible, and competitive inhibitor of acetyl-CoA carboxylase (ACC). TOFA is a key enzyme involved in fatty acid biosynthesis. TOFA inhibits cellular fatty acid synthesis in a dose-dependent manner (IC50 = 4 μM in human breast cancer cell line MCF7).

Nota de preparo

TOFA is soluble in DMSO at a concentration that is greater than 2 mg/ml.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 2

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)

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Certificados de análise (COA)

Lot/Batch Number
BGBC2290
028K46172
028K46171
028K4617
094K4609

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Sigma-Aldrich

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Acetyl-CoA Carboxylase 1 human

Weibo Zhou et al.
Cancer research, 67(7), 2964-2971 (2007-04-06)
Fatty acid synthase (FAS), the enzyme responsible for the de novo synthesis of fatty acids, is highly expressed in ovarian cancers and most common human carcinomas. Inhibition of FAS and activation of AMP-activated protein kinase (AMPK) have been shown to
Effects of a novel dual lipid synthesis inhibitor and its potential utility in treating dyslipidemia and metabolic syndrome
Cramer CT, et al.
Journal of Lipid Research, 45(7), 1289-1301 (2004)
Fanconi anemia mesenchymal stromal cells-derived glycerophospholipids skew hematopoietic stem cell differentiation through toll-like receptor signaling
Amarachintha S, et al.
Stem Cells, 33(11), 3382-3396 (2015)
Modulation of lipolysis and glycolysis pathways in cancer stem cells changed multipotentiality and differentiation capacity toward endothelial lineage
Pouyafar A, et al.
Cell & Bioscience, 9(1), 30-30 (2019)
Weibo Zhou et al.
Cancer research, 63(21), 7330-7337 (2003-11-13)
C75, an inhibitor of fatty acid synthase (FAS), induces apoptosis in cultured human cancer cells. Its proposed mechanism of action linked high levels of malonyl-CoA after FAS inhibition to potential downstream effects including inhibition of carnitine palmitoyltransferase-1 (CPT-1) with resultant
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