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373605

Sigma-Aldrich

6,6′-Dithiodinicotinic acid

technical grade, 85%

Synonym(s):

Bis[3-Carboxypyridine] 6,6′-disulfide, Bis[3-carboxypyridine] 6,6′-disulfide

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About This Item

Empirical Formula (Hill Notation):
C12H8N2O4S2
CAS Number:
15658-35-2
Molecular Weight:
308.33
EC Number:
239-729-6
MDL number:
MFCD00006454
UNSPSC Code:
12352100
PubChem Substance ID:
24863248
NACRES:
NA.22

grade

technical grade

assay

85%

form

solid

mp

263-265 °C (lit.)

SMILES string

OC(=O)c1ccc(SSc2ccc(cn2)C(O)=O)nc1

InChI

1S/C12H8N2O4S2/c15-11(16)7-1-3-9(13-5-7)19-20-10-4-2-8(6-14-10)12(17)18/h1-6H,(H,15,16)(H,17,18)

InChI key

GSASOFRDSIKDSN-UHFFFAOYSA-N

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General description

6,6′-Dithiodinicotinic acid is reported as sulphydryl reagent. 6,6′-Dithiodinicotinic acid is reported to react with thiols, to afford a disulfide and 6-mercaptonicotinic acid. Interaction of 6,6′-dithiodinicotinic acid with the homogenates of Ehrlich ascites cells has been reported.

Application

6,6′-Dithiodinicotinic acid may be employed as:
  • specific thiol blocker to investigate the radioprotective effect of mercaptoethylamine on the thiol level of the outer cell membrane of the Ehrlich ascites tumor cells
  • modifier to investigate the polar microenvironment around the reactive Cys283 of rabbit muscle creatine kinase
  • dipyridyl-dithio substrate to evaluate the protein disulfide-thiol interchange activity of the auxin stimulated NADH: protein disulfide reductase (NADH oxidase) of soybean plasma membranes
  • water-soluble reagent in a study for introducing, in buffered saline, a reactive sulfhydryl group on water-soluble molecules bearing an alkyl-amino group
  • chromogen for sulfhydryl groups in the Ellman method for cholinesterase determinations
  • spectrophotometric determination of thiols and of total glutathione in human blood

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000237940
0000205666
0000164890
0000210532
MKBM7197V

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M M Konstantinova et al.
Radiobiologiia, 28(3), 364-368 (1988-05-01)
In experiments with Ehrlich ascites tumor cells, using a specific thiol blocker, 6,6'-dithiodinicotinic acid, that does not penetrate the cell and therefore only binds SH-groups of peripheral areas of an external cell membrane, it was demonstrated that (1) the external
Metastases limited.
D R Grassetti
Nature, 308(5959), 500-500 (1984-04-05)
L Meunier et al.
Bioconjugate chemistry, 10(2), 206-212 (1999-03-17)
A simple method for introducing, in buffered saline, a reactive sulfhydryl group on water-soluble molecules bearing an alkyl-amino group is described. This method is based on the use of two water-soluble reagents: 2-iminothiolane and 6,6'-dithiodinicotinic acid. The first one is
[Quantitation of sulfhydryl groups on surface of erythrocytes].
X B Liu et al.
Zhongguo yi xue ke xue yuan xue bao. Acta Academiae Medicinae Sinicae, 8(2), 146-147 (1986-04-01)
The determination of thiols and of total glutathione in human blood using 6,6'-dithiodinicotinic acid (CPDS).
D R Grassetti et al.
Biochemical medicine, 12(2), 149-153 (1975-02-11)
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