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O4000

Sigma-Aldrich

Oxythiamine chloride hydrochloride

≥95% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C12H16ClN3O2S · HCl
CAS Number:
Molecular Weight:
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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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.
Functional thiamine deficiency in end-stage renal disease: malnutrition despite ample nutrients
Moradi H and Said HM
Kidney International, 90(2), 252-254 (2016)
Thiamine antimetabolite causes functional thiamine deficiency in patients with end stage renal disease
Zhang F, et al.
Kidney International, 90(2), 396-403 (2016)
Inhibition of transketolase by oxythiamine altered dynamics of protein signals in pancreatic cancer cells
Wang J, et al.
Experimental Hematology & Oncology, 2(1), 18-18 (2013)
Novel structural aspects of oxythiamine, an antagonist of thiamine. Crystal structures of three salts,(oxythiamineH)(picrolonate) 2textperiodcentered
Hu NH, et al.
Inorgorganica Chimica Acta, 295(1), 71-83 (1999)

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