Hydroxyphenylazopyrimidines: Characterization of the Active Forms and Their Inhibitory Action on a DNA Polymerase from Bacillus subtilis | Zendy

John M. MacKenzie | Zendy; Marilyn M. Neville | Zendy; George E. Wright | Zendy; Neal C. Brown | Zendy

Open Access

Hydroxyphenylazopyrimidines: Characterization of the Active Forms and Their Inhibitory Action on a DNA Polymerase from Bacillus subtilis

Author(s) -

John M. MacKenzie,

Marilyn M. Neville,

George E. Wright,

Neal C. Brown

Publication year - 1973

Publication title -

proceedings of the national academy of sciences

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.011

H-Index - 771

eISSN - 1091-6490

pISSN - 0027-8424

DOI - 10.1073/pnas.70.2.512

Subject(s) - bacillus subtilis , dna , inhibitory postsynaptic potential , chemistry , action (physics) , dna polymerase , polymerase , biochemistry , biology , genetics , bacteria , physics , quantum mechanics , neuroscience

The active forms of 6-(p-hydroxyphenylazo)-uracil and 6-(p-hydroxyphenylazo)-isocytosine were isolated and identified as their respective hydrazino derivatives. These arylhydrazino pyrimidines selectively inhibited a chromatographically distinct DNA polymerase from Bacillus subtilis. The actions of the reduced drugs on this polymerase were identical to those observed on ATP-dependent DNA synthesis in toluene-treated cells; dGTP competitively antagonized the inhibitory activity of the uracil derivative, and dATP competitively antagonized that of the isocytosine derivative. Analysis of the interactions of the arylhydrazinopyrimidines and nucleic acid bases by nuclear magnetic resonance suggested that hydroxyphenylhydrazino-uracil and hydroxyphenylhydrazino-isocytosine pair in a novel manner with, respectively, cytosine and thymine. A mechanism of inhibitor action, involving binding of the reduced drugs to enzyme and the pyrimidines of DNA template, is proposed.

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