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In and out of the minor groove: interaction of an AT-rich DNA with the drug CD27.

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Acosta-Reyes FJ, Dardonville C, de Koning HP, Natto M, Subirana JA, Campos JL
OpenAccess logo Acta Crystallogr D Biol Crystallogr 70 1614-21 (2014)
Cited: 7 times
EuropePMC logo PMID: 24914972

Abstract

The DNA of several pathogens is very rich in AT base pairs. Typical examples include the malaria parasite Plasmodium falciparum and the causative agents of trichomoniasis and trypanosomiases. This fact has prompted studies of drugs which interact with the minor groove of DNA, some of which are used in medical practice. Previous studies have been performed almost exclusively with the AATT sequence. New features should be uncovered through the study of different DNA sequences. In this paper, the crystal structure of the complex of the DNA duplex d(AAAATTTT)2 with the dicationic drug 4,4'-bis(imidazolinylamino)diphenylamine (CD27) is presented. The drug binds to the minor groove of DNA as expected, but it shows two new features that have not previously been described: (i) the drugs protrude from the DNA and interact with neighbouring molecules, so that they may act as cross-linking agents, and (ii) the drugs completely cover the whole minor groove of DNA and displace bound water. Thus, they may prevent the access to DNA of proteins such as AT-hook proteins. These features are also expected for other minor-groove binding drugs when associated with all-AT DNA. These findings allow a better understanding of this family of compounds and will help in the development of new, more effective drugs. New data on the biological interaction of CD27 with the causative agent of trichomoniasis, Trichomonas vaginalis, are also reported.

Articles - 4ocd mentioned but not cited (1)

  1. In and out of the minor groove: interaction of an AT-rich DNA with the drug CD27. Acosta-Reyes FJ, Dardonville C, de Koning HP, Natto M, Subirana JA, Campos JL. Acta Crystallogr D Biol Crystallogr 70 1614-1621 (2014)


Articles citing this publication (6)

  1. Functional and structural analysis of AT-specific minor groove binders that disrupt DNA-protein interactions and cause disintegration of the Trypanosoma brucei kinetoplast. Millan CR, Acosta-Reyes FJ, Lagartera L, Ebiloma GU, Lemgruber L, Nué Martínez JJ, Saperas N, Dardonville C, de Koning HP, Campos JL. Nucleic Acids Res 45 8378-8391 (2017)
  2. First Structure of a Designed Minor Groove Binding Heterocyclic Cation that Specifically Recognizes Mixed DNA Base Pair Sequences. Harika NK, Germann MW, Wilson WD. Chemistry 23 17612-17620 (2017)
  3. How do non-covalent complexes dissociate in droplets? A case study of the desolvation of dsDNA from a charged aqueous nanodrop. Sharawy M, Consta S. Phys Chem Chem Phys 17 25550-25562 (2015)
  4. Understanding the guanidine-like cationic moiety for optimal binding into the DNA minor groove. O'Sullivan P, Rozas I. ChemMedChem 9 2065-2073 (2014)
  5. Binding of resveratrol to the minor groove of DNA sequences with AATT and TTAA segments induces differential stability. Nair MS, D'Mello S, Pant R, Poluri KM. J Photochem Photobiol B 170 217-224 (2017)
  6. Synthesis and Biophysical and Biological Studies of N-Phenylbenzamide Derivatives Targeting Kinetoplastid Parasites. Nué-Martinez JJ, Cisneros D, Moreno-Blázquez MDV, Fonseca-Berzal C, Manzano JI, Kraeutler D, Ungogo MA, Aloraini MA, Elati HAA, Ibáñez-Escribano A, Lagartera L, Herraiz T, Gamarro F, de Koning HP, Gómez-Barrio A, Dardonville C. J Med Chem 66 13452-13480 (2023)


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