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Merck

O4000

Sigma-Aldrich

Oxythiamine chloride hydrochloride

≥95% (HPLC)

Sinónimos:

5-(2-Hydroxyethyl)-3-(4-hydroxy-2-methyl-5-pyrimidinylmethyl)-4-methylthiazolium chloride

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About This Item

Fórmula empírica (notación de Hill):
C12H16ClN3O2S · HCl
Número de CAS:
Peso molecular:
338.25
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.79

Quality Level

assay

≥95% (HPLC)

form

powder

technique(s)

HPLC: suitable

color

white to off-white

storage temp.

−20°C

SMILES string

CC(N1)=NC=C(C[N+]2=CSC(CCO)=C2C)C1=O.Cl.[Cl-]

InChI

1S/C12H16N3O2S.2ClH/c1-8-11(3-4-16)18-7-15(8)6-10-5-13-9(2)14-12(10)17;;/h5,7,16H,3-4,6H2,1-2H3,(H,13,14,17);2*1H

InChI key

QHUYPZVMEJLSEB-UHFFFAOYSA-N

General description

Oxythiamine is a thiamine antimetabolite and the source through diet is by consuming acidic thiamine rich foods.

Application

Oxythiamine chloride hydrochloride is suitable for use:
  • as a reference standard for calibration curve generation in liquid chromatography-tandem mass spectrometry (LC-MS/MS) for oxythiamine pyrophosphate (OTPP) quantification in red blood cells
  • as a thiamine transport inhibitor in human mammary epithelial cells (HMEC) and breast cancer cell lines
  • in the synthesis of oxythiamineH picrolonate salt

Biochem/physiol Actions

Oxythiamine (OT) is a thiamine antagonist. It is a transketolase inhibitor and is employed to study anti-metastatic mechanisms, especially those involving metalloproteinases (MMP). It significantly sensitizes human hepatocellular carcinoma cells (HCC) to sorafenib, favoring tumor suppression.
Oxythiamine inhibits Transketolase, the enzyme that controls the nonoxidative branch of the pentose phosphate pathway.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Visite la Librería de documentos

Functional thiamine deficiency in end-stage renal disease: malnutrition despite ample nutrients
Moradi H and Said HM
Kidney International, 90(2), 252-254 (2016)
Chih-Min Yang et al.
Clinical & experimental metastasis, 27(5), 341-349 (2010-05-08)
This study examined the anti-metastatic effects of oxythiamine (OT) both in cell culture and in vivo. Cell culture results revealed that OT (0-20 microM) significantly inhibited the invasion and migration (IC(50) = 8.75 microM) of Lewis lung carcinoma (LLC) cells.
Hengwei Zhang et al.
Journal of proteome research, 9(2), 980-989 (2009-12-29)
Oxythiamine (OT), a transketolase inhibitor, is known to inhibit pancreatic cancer cell proliferation. In this study, we investigated the effect of inhibition of the transketolase pathway on signaling pathways in MIA PaCa cancer cells using in-house proteomic techniques. We hypothesized
Thiamine and selected thiamine antivitamins?biological activity and methods of synthesis
Tylicki A, et al.
Bioscience Reports, 38(1), BSR20171148-BSR20171148 (2018)
Emerging role of the pentose phosphate pathway in hepatocellular carcinoma
Kowalik MA, et al.
Frontiers in Oncology, 7, 87-87 (2017)

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