Hydrogen bonding in deoxyribonucleic acid base recognition. 2. Deoxyribonucleic acid binding studies of acridine alkylamides.

A series of derivatives of 2-methoxy-6-chloro-9-aminoacridine bearing side chains terminated by various groups, such as carboxamide, N-methylcarboxamide, N,N-dimethylcarboxamide, methyl ester, and methyl were synthesized. The interaction of these intercalating dyes with DNA of various GC content was studied comparatively by using equilibrium dialysis and fluorescence spectroscopy. The results showed that the compounds bearing a chain terminated by a free carboxamide group could interact specifically with GC-rich DNA provided that the length and conformation of the side chain were appropriate. From these results in hand as well as those reported in the preceding paper (NMR studies at the minihelix level) it is thought that the G specificity of these compounds arises from their ability to form hydrogen bonds between the terminal carboxamide group borne by their side chain and the NH2 and N3 of the adjacent guanine located in the small grove.

[1]  R. Simpson,et al.  Conformation of 145 base pair length poly (dG-dC) . poly (dG-dC) in solution and in association with histones. , 1980, Nucleic acids research.

[2]  A. Leslie,et al.  Left-handed DNA helices , 1980, Nature.

[3]  B. Hingerty,et al.  Conformational origin of the pyrimidine (3'-5') purine base sequence preference for intercalation into RNAs. , 1979, Biopolymers.

[4]  R. Simpson,et al.  An alternating conformation characterizes the phosphodiester backbone of poly(dA-dT) in solution. , 1979, The Journal of biological chemistry.

[5]  P. Dessen,et al.  Deoxyribonucleic acid bifunctional intercalators: kinetic investigation of the binding of several acridine dimers to deoxyribonucleic acid. , 1979, Biochemistry.

[6]  A Klug,et al.  A hypothesis on a specific sequence-dependent conformation of DNA and its relation to the binding of the lac-repressor protein. , 1979, Journal of molecular biology.

[7]  F. Pohl,et al.  "Alternating B-DNA" conformation for the oligo(dG-dC) duplex in high-salt solution. , 1979, Proceedings of the National Academy of Sciences of the United States of America.

[8]  T M Jovin,et al.  Fluorescence decay analysis in solution and in a microscope of DNA and chromosomes stained with quinacrine. , 1979, The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society.

[9]  R. Burgess,et al.  Nonspecific interactions of Escherichia coli RNA polymerase with native and denatured DNA: differences in the binding behavior of core and holoenzyme. , 1978, Biochemistry.

[10]  R. Burgess,et al.  Measurement of binding constants for protein-DNA interactions by DNA-cellulose chromatography. , 1977, Biochemistry.

[11]  C. Hélène.  Specific recognition of guanine bases in protein—nucleic acid complexes , 1977, FEBS letters.

[12]  N. Seeman,et al.  Sequence-specific Recognition of Double Helical Nucleic Acids by Proteins (base Pairs/hydrogen Bonding/recognition Fidelity/ion Binding) , 2022 .

[13]  M Le Bret,et al.  DNA polyintercalating drugs: DNA binding of diacridine derivatives. , 1975, Proceedings of the National Academy of Sciences of the United States of America.

[14]  M. Leng,et al.  Effect of DNA base composition on the intercalation of proflavine. A kinetic study. , 1975, Biophysical chemistry.

[15]  D. Crothers,et al.  Interactions of heteroaromatic compounds with nucleic acids. 1. The influence of heteroatoms and polarizability on the base specificity of intercalating ligands. , 1975, European journal of biochemistry.

[16]  S. Arnott,et al.  Structures for the polynucleotide complexes poly(dA) with poly (dT) and poly(dT) with poly(dA) with poly (dT). , 1974, Journal of molecular biology.

[17]  S. Arnott,et al.  Structural details of double-helix observed for DNAs containing alternating purine and pyrimidine sequences. , 1974, Journal of molecular biology.

[18]  D. Crothers,et al.  A non-intercalating proflavine derivative. , 1973, European journal of biochemistry.

[19]  H. M. Sobell,et al.  Stereochemistry of actinomycin binding to DNA. I. Refinement and further structural details of the actinomycin-deoxyguanosine crystalline complex. , 1972, Journal of molecular biology.

[20]  T M Jovin,et al.  Salt-induced co-operative conformational change of a synthetic DNA: equilibrium and kinetic studies with poly (dG-dC). , 1972, Journal of molecular biology.

[21]  R. Rigler,et al.  Quantum yield of acridines interacting with DNA of defined sequence. A basis for the explanation of acridine bands in chromosomes. , 1972, Experimental cell research.

[22]  J. Ramstein,et al.  Interaction between proflavine and deoxyribonucleic acid influence of DNA base composition. , 1972, Biochemical and biophysical research communications.

[23]  B. Weisblum,et al.  Quinacrine, a chromosome stain specific for deoxyadenylate-deoxythymidylaterich regions in DNA. , 1972, Proceedings of the National Academy of Sciences of the United States of America.

[24]  S. Bram.  Secondary structure of DNA depends on base composition. , 1971, Nature: New biology.

[25]  B. Révet,et al.  Direct determination of the superhelix density of closed circular DNA by viscometric titration. , 1971, Nature: New biology.

[26]  M. Laskowski.  12 Deoxyribonuclease I , 1971 .

[27]  J. Le Pecq,et al.  The change of the torsion of the DNA helix caused by intercalation. II. Measurement of the relative change of torsion induced by various intercalating drugs. , 1971, Biochimie.

[28]  C. Cantor,et al.  Physicochemical studies on polydeoxyribonucleotides containing defined repeating nucleotide sequences. , 1970, Journal of molecular biology.

[29]  S. Arnott,et al.  The geometry of nucleic acids. , 1970, Progress in biophysics and molecular biology.

[30]  R. L. Baldwin,et al.  X-ray studies on two synthetic DNA copolymers. , 1963, Journal of molecular biology.