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Key Documents

O4000

Sigma-Aldrich

Oxythiamine chloride hydrochloride

≥95% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C12H16ClN3O2S · HCl
Numéro CAS:
Poids moléculaire :
338.25
Numéro MDL:
Code UNSPSC :
12352116
ID de substance PubChem :
Nomenclature NACRES :
NA.79

Niveau de qualité

Pureté

≥95% (HPLC)

Forme

powder

Technique(s)

HPLC: suitable

Couleur

white to off-white

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

QHUYPZVMEJLSEB-UHFFFAOYSA-N

Description générale

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

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)


Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

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
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.
Thiamine antimetabolite causes functional thiamine deficiency in patients with end stage renal disease
Zhang F, et al.
Kidney International, 90(2), 396-403 (2016)
Functional thiamine deficiency in end-stage renal disease: malnutrition despite ample nutrients
Moradi H and Said HM
Kidney International, 90(2), 252-254 (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)

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