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Interactions of 4-nitroquinoline 1-oxide with deoxyribodinucleotides

Journal Article · · Biochemistry; (United States)
DOI:https://doi.org/10.1021/bi00585a001· OSTI ID:5483995
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The interactions of 4-nitroquinoline 1-oxide (NQO), a potent mutagen and carcinogen, with several self- and non-self-complementary deoxydinucleotides were probed by using absorption spectra of the charge transfer bands and /sup 1/H and /sup 13/C NMR spectra. Absorption spectra were analyzed by using Benesi-Hildebrand-type equations to yield stoichiometries and equilibrium constants of complex formation. Non-self-complementary dimers from weak 1:1 complexes (dpTpG:NQO,K(25/sup 0/C) = 22 MA/sup -1/) while self-complementary dimers form strong 2:1 complexes ((dpCpG)/sub 2/:NQO,K(25/sup 0/C) = 2.2 x 10/sup 4/ M/sup -2/). A mixture of dpTpG and dpCpA with NQO gives a 2:1 complex (dpTpG:NQO:dpCpA,K(25/sup 0/C) = 8.6 x 10/sup 3/ M/sup -2/). Analyses of the chnges in /sup 13/C and /sup 1/H NMR chemical shifts with complex formation gave approximate orientations for the intercalation of NQO with self-complementary dimer minihelixes. In the (dpCpG)/sub 2/:NQO and (dpGpC)/sub 2/:NQO complexes, the NO/sub 2/ group of NQO probably lies in the major grove and the NO/sub 2/, NO containing NQO ring is stacked near th purine imidazole ring. In the (dpTpA)/sub 2/:NQO and (dpApT)/sub 2/NWO complexes, the NO/sub 2/ seems to project into the minor grove and the NQO benzenoid ring is over the purine imidazole ring.

Research Organization:
Univ. of California, Berkeley
DOE Contract Number:
W-7405-ENG-48
OSTI ID:
5483995
Journal Information:
Biochemistry; (United States), Journal Name: Biochemistry; (United States) Vol. 18:18; ISSN BICHA
Country of Publication:
United States
Language:
English

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Related Subjects

550200* -- Biochemistry
59 BASIC BIOLOGICAL SCIENCES
ABSORPTION SPECTRA
AZINES
CARBON 13
CARBON ISOTOPES
CARCINOGENS
CHALCOGENIDES
DATA
DATA FORMS
DIMERS
DNA
EVEN-ODD NUCLEI
EXPERIMENTAL DATA
GRAPHS
HETEROCYCLIC COMPOUNDS
HYDROGEN 1
HYDROGEN ISOTOPES
INFORMATION
ISOTOPES
LIGHT NUCLEI
MUTAGENS
NITRO COMPOUNDS
NMR SPECTRA
NUCLEI
NUCLEIC ACIDS
NUCLEOTIDES
NUMERICAL DATA
ODD-EVEN NUCLEI
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
OXIDES
OXYGEN COMPOUNDS
PYRIDINES
QUINOLINES
SPECTRA
STABLE ISOTOPES
STOICHIOMETRY
STRUCTURAL CHEMICAL ANALYSIS