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373605

Sigma-Aldrich

6,6′-Dithiodinicotinic acid

technical grade, 85%

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Synonym(s):
Bis[3-Carboxypyridine] 6,6′-disulfide, Bis[3-carboxypyridine] 6,6′-disulfide
Empirical Formula (Hill Notation):
C12H8N2O4S2
CAS Number:
Molecular Weight:
308.33
EC Number:
MDL number:
PubChem Substance ID:
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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1 of 4

This Item
43761109010D8130
vibrant-m

373605

6,6′-Dithiodinicotinic acid

-
vibrant-m

43761

2,2′-Dithiodibenzoic acid

-
vibrant-m

109010

3,3′-Dithiodipropionic acid

-
vibrant-m

D8130

5,5′-Dithiobis(2-nitrobenzoic acid)

Essential+ Grade
mp

263-265 °C (lit.)

mp

287-290 °C (lit.), 288-293 °C

mp

155-158 °C (lit.)

mp

240-245 °C (dec.) (lit.)

form

solid

form

-

form

-

form

powder

grade

technical grade

grade

-

grade

-

grade

-

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

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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Slide 1 of 6

1 of 6

The interaction of 6,6'-dithiodinicotinic acid with thiols and with ehrlich ascites tumor cells.
D R Grassetti et al.
Biochemical pharmacology, 18(3), 603-611 (1969-03-01)
S Willig et al.
Veterinary and human toxicology, 38(4), 249-253 (1996-08-01)
The Ellman method for cholinesterase determination is a spectrophotometric method which entails the use of 5,5'-dithiobis-(2-nitrobenzoic) acid (DTNB) as a chromogen and records the level of cholinesterase activity as the change in absorbance at 412 nm. Although this procedure commonly
Timo Wille et al.
Toxicology mechanisms and methods, 21(7), 533-537 (2011-04-08)
For the diagnosis and therapy monitoring of intoxications with organophosphorus compounds, the determination of acetylcholinesterase (AChE) activity in whole blood is crucial. Usually, this testing is done with the colorimetric Ellman test using 412 nm wavelength and 5,5'-dithiobis-nitrobenzoic acid (DTNB) as
D J Morré et al.
Molecular and cellular biochemistry, 200(1-2), 7-13 (1999-11-24)
Dipyridyl-dithio substrates were cleaved by isolated vesicles of plasma membranes prepared from etiolated hypocotyls of soybean. The cleavage was stimulated by auxins at physiological concentrations. The substrates utilized were principally 2,2'-dithiodipyridine (DTP) and 6,6'-dithiodinicotinic acid (DTNA). The DTP generated 2
J Nishiyama et al.
Analytical biochemistry, 138(1), 95-98 (1984-04-01)
A simple and rapid method for the determination of nanomole levels of biological thiols is described. The analysis is based on the combination of reverse-phase high-performance liquid chromatography with a postcolumn reaction with 6,6'-dithiodinicotinic acid. Thiols, including cysteine, cysteamine, thiolhistidine

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