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Chemical Compound Review:

AC1LEJPY pyridine-3-carbothioamide

Synonyms: AG-F-59262, ACMC-209k6f, ANW-30421, NSC-18336, ACN-000013, ...

Sousa, E.H. et al., Male, K.B. et al., Ruse, M.J. et al., Templeton, D.M. et al., Shen, Y.Q. et al., et al.

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Disease relevance of thionicotinamide

SK&F-525-A, the cytochrome P-450 inhibitor, did not affect either thioamide-induced toxicity or levels of excretion of TNA S-oxide; however, the role of the P-450 isoenzymes cannot be totally ruled out [1].

High impact information on thionicotinamide

Reduced thionicotinamide adenine dinucleotide phosphate quenched the fluorescence of bound nucleotide [2].
While, in the green or blue subunit, the SNAD(+) binds in a non-productive manner, resulting in a disordered thionicotinamide ring and rearranged active-site residues [3].
In an attempt to shed light on the activation of thioamide drugs, we have mimicked a redox process involving the thionicotinamide (thio) ligand, investigating its reactivity through coordination to the redox reversible [Fe(III/II)(CN)(5)(H(2)O)](2-/3-) metal center [4].
A kinetic study for the cross-reaction of thionicotinamide and [Fe(CN)(6)](3-) was also carried out [4].
Electron transfer kinetics and mechanistic study of the thionicotinamide coordinated to the pentacyanoferrate(III)/(II) complexes: a model system for the in vitro activation of thioamides anti-tuberculosis drugs [4].

Biological context of thionicotinamide

0. The rate of this reaction is strongly dependent on pH due to an acid-base equilibrium related to the deprotonation of the R-SH functional group of the imidothiol form of thionicotinamide [4].

Associations of thionicotinamide with other chemical compounds

The oxidation of thionicotinamide by [Fe(CN)(6)](3-) leads to formation of mainly 3-cyanopyridine and [Fe(CN)(6)](4-) with a k(et)=(5.38+/-0.03) M(-1)s(-1) at 25 degrees C, pH 12 [4].
Regulation of coenzyme utilization by bovine liver glutamate dehydrogenase: investigations using thionicotinamide analogues of NAD and NADP in a dual wavelength assay [5].
The transhydrogenation between NADH and thionicotinamide nucleotide or acetylpyridine nucleotide is shown to proceed via a Ping Pong or an ordered Bi Bi mechanism, respectively, at pH above 7 [6].

Gene context of thionicotinamide

1. The coenzyme preference of bovine liver glutamate dehydrogenase (GDH) was probed using dual wavelength spectroscopy and pairing the thionicotinamide analogues, S-NAD or S-NADP (which have absorbance maxima at 400 nm), with the natural coenzymes, NADP or NAD [5].

References

The effect of methimazole on thioamide bioactivation and toxicity. Ruse, M.J., Waring, R.H. Toxicol. Lett. (1991) [Pubmed]
Fluorescence energy transfer between heterologous active sites of affinity-labeled aspartokinase of Escherichia coli. Wright, K., Takahashi, M. Biochemistry (1977) [Pubmed]
Structures of D-glyceraldehyde-3-phosphate dehydrogenase complexed with coenzyme analogues. Shen, Y.Q., Song, S.Y., Lin, Z.J. Acta Crystallogr. D Biol. Crystallogr. (2002) [Pubmed]
Electron transfer kinetics and mechanistic study of the thionicotinamide coordinated to the pentacyanoferrate(III)/(II) complexes: a model system for the in vitro activation of thioamides anti-tuberculosis drugs. Sousa, E.H., Pontes, D.L., Diógenes, I.C., Lopes, L.G., Oliveira, J.S., Basso, L.A., Santos, D.S., Moreira, I.S. J. Inorg. Biochem. (2005) [Pubmed]
Regulation of coenzyme utilization by bovine liver glutamate dehydrogenase: investigations using thionicotinamide analogues of NAD and NADP in a dual wavelength assay. Male, K.B., Storey, K.B. Int. J. Biochem. (1982) [Pubmed]
Kinetic and spectroscopic studies of transhydrogenase activity and nucleotide site of lipoamide dehydrogenase. Templeton, D.M., Tsai, C.S. Int. J. Biochem. (1985) [Pubmed]

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