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. 1988 Sep 26;16(18):8999–9016. doi: 10.1093/nar/16.18.8999

A molecular model for proflavine-DNA intercalation.

S Neidle 1, L H Pearl 1, P Herzyk 1, H M Berman 1
PMCID: PMC338648  PMID: 3174439

Abstract

A molecular model has been derived for the intercalation of proflavine into the CpG site of the decamer duplex of d(GATACGATAC). The starting geometry of the intercalation site was taken from previous crystallographic studies on the d(CpG)-proflavine complex, and molecular mechanics used to obtain a stereochemically acceptable structure. This has widened grooves compared to standard A- or B- double helices, as well as distinct conformational, roll, twist and tilt features.

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Selected References

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  1. Alden C. J., Arnott S. Stereochemical model for proflavin intercalation in A-DNA. Nucleic Acids Res. 1977 Nov;4(11):3855–3861. doi: 10.1093/nar/4.11.3855. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Alden C. J., Arnott S. Visualization of planar drug intercalations in B-DNA. Nucleic Acids Res. 1975 Oct;2(10):1701–1717. doi: 10.1093/nar/2.10.1701. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Berman H. M., Neidle S., Stodola R. K. Drug-nucleic acid interactions: conformational flexibility at the intercalation site. Proc Natl Acad Sci U S A. 1978 Feb;75(2):828–832. doi: 10.1073/pnas.75.2.828. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Berman H. M., Young P. R. The interaction of intercalating drugs with nucleic acids. Annu Rev Biophys Bioeng. 1981;10:87–114. doi: 10.1146/annurev.bb.10.060181.000511. [DOI] [PubMed] [Google Scholar]
  5. Calladine C. R. Mechanics of sequence-dependent stacking of bases in B-DNA. J Mol Biol. 1982 Oct 25;161(2):343–352. doi: 10.1016/0022-2836(82)90157-7. [DOI] [PubMed] [Google Scholar]
  6. Chaires J. B., Fox K. R., Herrera J. E., Britt M., Waring M. J. Site and sequence specificity of the daunomycin-DNA interaction. Biochemistry. 1987 Dec 15;26(25):8227–8236. doi: 10.1021/bi00399a031. [DOI] [PubMed] [Google Scholar]
  7. Dervan P. B. Design of sequence-specific DNA-binding molecules. Science. 1986 Apr 25;232(4749):464–471. doi: 10.1126/science.2421408. [DOI] [PubMed] [Google Scholar]
  8. Dickerson R. E. Base sequence and helix structure variation in B and A DNA. J Mol Biol. 1983 May 25;166(3):419–441. doi: 10.1016/s0022-2836(83)80093-x. [DOI] [PubMed] [Google Scholar]
  9. Dickerson R. E., Drew H. R. Structure of a B-DNA dodecamer. II. Influence of base sequence on helix structure. J Mol Biol. 1981 Jul 15;149(4):761–786. doi: 10.1016/0022-2836(81)90357-0. [DOI] [PubMed] [Google Scholar]
  10. Drew H. R., Travers A. A. DNA structural variations in the E. coli tyrT promoter. Cell. 1984 Jun;37(2):491–502. doi: 10.1016/0092-8674(84)90379-9. [DOI] [PubMed] [Google Scholar]
  11. Drew H. R., Travers A. A. Structural junctions in DNA: the influence of flanking sequence on nuclease digestion specificities. Nucleic Acids Res. 1985 Jun 25;13(12):4445–4467. doi: 10.1093/nar/13.12.4445. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Ford K., Fox K. R., Neidle S., Waring M. J. DNA sequence preferences for an intercalating porphyrin compound revealed by footprinting. Nucleic Acids Res. 1987 Mar 11;15(5):2221–2234. doi: 10.1093/nar/15.5.2221. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Fratini A. V., Kopka M. L., Drew H. R., Dickerson R. E. Reversible bending and helix geometry in a B-DNA dodecamer: CGCGAATTBrCGCG. J Biol Chem. 1982 Dec 25;257(24):14686–14707. [PubMed] [Google Scholar]
  14. Lybrand T. P., Brown S. C., Creighton S., Shafer R. H., Kollman P. A. Computer modeling of actinomycin D interactions with double-helical DNA. J Mol Biol. 1986 Oct 5;191(3):495–507. doi: 10.1016/0022-2836(86)90144-0. [DOI] [PubMed] [Google Scholar]
  15. Lybrand T., Kollman P. Molecular mechanical calculations on the interaction of ethidium cation with double-helical DNA. Biopolymers. 1985 Oct;24(10):1863–1879. doi: 10.1002/bip.360241003. [DOI] [PubMed] [Google Scholar]
  16. Miller K. J., Pycior J. F. Interaction of molecules with nucleic acids. II. Two pairs of families of intercalation sites, unwinding angles, and the neighbor-exclusion principle. Biopolymers. 1979 Nov;18(11):2683–2719. doi: 10.1002/bip.1979.360181105. [DOI] [PubMed] [Google Scholar]
  17. Neidle S., Pearl L. H., Skelly J. V. DNA structure and perturbation by drug binding. Biochem J. 1987 Apr 1;243(1):1–13. doi: 10.1042/bj2430001. [DOI] [PMC free article] [PubMed] [Google Scholar]
  18. Pommier Y., Minford J. K., Schwartz R. E., Zwelling L. A., Kohn K. W. Effects of the DNA intercalators 4'-(9-acridinylamino)methanesulfon-m-anisidide and 2-methyl-9-hydroxyellipticinium on topoisomerase II mediated DNA strand cleavage and strand passage. Biochemistry. 1985 Nov 5;24(23):6410–6416. doi: 10.1021/bi00344a015. [DOI] [PubMed] [Google Scholar]
  19. Shakked Z., Rabinovich D. The effect of the base sequence on the fine structure of the DNA double helix. Prog Biophys Mol Biol. 1986;47(3):159–195. doi: 10.1016/0079-6107(86)90013-1. [DOI] [PubMed] [Google Scholar]
  20. Shieh H. S., Berman H. M., Dabrow M., Neidle S. The structure of drug-deoxydinucleoside phosphate complex; generalized conformational behavior of intercalation complexes with RNA and DNA fragments. Nucleic Acids Res. 1980 Jan 11;8(1):85–97. doi: 10.1093/nar/8.1.85. [DOI] [PMC free article] [PubMed] [Google Scholar]
  21. Sobell H. M., Jain S. C. Stereochemistry of actinomycin binding to DNA. II. Detailed molecular model of actinomycin-DNA complex and its implications. J Mol Biol. 1972 Jul 14;68(1):21–34. doi: 10.1016/0022-2836(72)90259-8. [DOI] [PubMed] [Google Scholar]
  22. Sobell H. M., Tsai C. C., Jain S. C., Gilbert S. G. Visualization of drug-nucleic acid interactions at atomic resolution. III. Unifying structural concepts in understanding drug-DNA interactions and their broader implications in understanding protein-DNA interactions. J Mol Biol. 1977 Aug 15;114(3):333–365. doi: 10.1016/0022-2836(77)90254-6. [DOI] [PubMed] [Google Scholar]
  23. Suck D., Lahm A., Oefner C. Structure refined to 2A of a nicked DNA octanucleotide complex with DNase I. Nature. 1988 Mar 31;332(6163):464–468. doi: 10.1038/332464a0. [DOI] [PubMed] [Google Scholar]
  24. Taylor E. R., Olson W. K. Theoretical studies of nucleic acid interactions. I. Estimates of conformational mobility in intercalated chains. Biopolymers. 1983 Dec;22(12):2667–2702. doi: 10.1002/bip.360221213. [DOI] [PubMed] [Google Scholar]
  25. Wang A. H., Ughetto G., Quigley G. J., Rich A. Interactions between an anthracycline antibiotic and DNA: molecular structure of daunomycin complexed to d(CpGpTpApCpG) at 1.2-A resolution. Biochemistry. 1987 Feb 24;26(4):1152–1163. doi: 10.1021/bi00378a025. [DOI] [PubMed] [Google Scholar]
  26. Wilson W. D., Jones R. L. Intercalating drugs: DNA binding and molecular pharmacology. Adv Pharmacol Chemother. 1981;18:177–222. doi: 10.1016/s1054-3589(08)60255-0. [DOI] [PubMed] [Google Scholar]
  27. Woodson S. A., Crothers D. M. Structural model for an oligonucleotide containing a bulged guanosine by NMR and energy minimization. Biochemistry. 1988 May 3;27(9):3130–3141. doi: 10.1021/bi00409a004. [DOI] [PubMed] [Google Scholar]
  28. Yang L., Rowe T. C., Nelson E. M., Liu L. F. In vivo mapping of DNA topoisomerase II-specific cleavage sites on SV40 chromatin. Cell. 1985 May;41(1):127–132. doi: 10.1016/0092-8674(85)90067-4. [DOI] [PubMed] [Google Scholar]

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