PMID: 3052587Oct 6, 1988

Photoinactivation of the thiamin transport system in Saccharomyces cerevisiae with azidobenzoyl derivatives of thiamin

Biochimica Et Biophysica Acta
K Sempuku

Abstract

In an attempt to obtain a potent inhibitor for thiamin transport of Saccharomyces cerivisiae three novel thiamin derivatives having an arylazido substituent in the thiazole moiety have been synthesized. The derivatives prepared were 4-azidobenzoylthiamin (ABT), 4-azidobenzoylthiamin disulfide (ABTD), and 4-azido-2-nitrobenzoylthiamin disulfide (ANBTD). Among the newly prepared photoreactive azidobenzoyl derivatives of thiamin, ANBTD showed the strongest competitive inhibition with an apparent Ki of 7.9 nM against thiamin uptake by S. cerevisiae IFO-2375. The Ki values for ABT, 4-azido-2-nitrobenzoylthiamin (ANBT), and ABTD were 187 nM, 83 nM, and 15 nM, respectively. When exposed to visible light, ANBTD inactivated in a time- and concentration-dependent manner the uptake of [14C]thiamin by yeast protoplasts as well as intact cells. Remaining activities of the thiamin uptake by the intact cells were 71.9%, 27.3%, 40.1%, and 15.0% after visible light irradiation for 15 min in the presence of 1 microM ABT, ANBT, ABTD, and ANBTD, respectively. The inactivation by ANBTD (0.05 microM) was partially prevented by previous addition of an excessive amount of thiamin (5 microM). Furthermore, it was found that ANBTD (0.5 microM) irreversib...Continue Reading

References

Mar 27, 1979·Biochimica Et Biophysica Acta·A Iwashima, H Nishimura
Jan 1, 1979·Annual Review of Biochemistry·V Chowdhry, F H Westheimer
Nov 2, 1979·Biochimica Et Biophysica Acta·A IwashimaY Nose
Jun 15, 1986·Experientia·H NishimuraA Iwashima
Dec 13, 1973·Biochimica Et Biophysica Acta·A IwashimaY Nose
Oct 1, 1971·Proceedings of the National Academy of Sciences of the United States of America·J M BeckerE Katchalski

Related Concepts

Azides
Cell Surface Proteins
Tissue Membrane
Photochemistry
Saccharomyces cerevisiae
Thiamine Mononitrate

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