ArticleBiochemistry2009
Crystal structure of a trypanocidal 4,4'-bis(imidazolinylamino)diphenylamine bound to DNA.
Article in Biochemistry, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed, 34 citations in OpenAlex.
- Kinetoplast-Directed Therapies: A Selective Mitochondrial Approach to Combat Leishmaniasis.Pharmaceuticals (Basel, Switzerland) · 2026Review
- Crystal structure of the HMGA AT-hook 1 domain bound to the minor groove of AT-rich DNA and inhibition by antikinetoplastid drugs.Scientific reports · 2024Article
- Crystal structures of 'ALternative Isoinformational ENgineered' DNA in B-form.Philosophical transactions of the Royal Society of London. Series B, Biological sciences · 2023Article
- Bound Compound, Interfacial Water, and Phenyl Ring Rotation Dynamics of a Compound in the DNA Minor Groove.Biochemistry · 2018Article
- Functional and structural analysis of AT-specific minor groove binders that disrupt DNA-protein interactions and cause disintegration of the Trypanosoma brucei kinetoplast.Nucleic acids research · 2017Article
- Toward an Expanded Genome: Structural and Computational Characterization of an Artificially Expanded Genetic Information System.Accounts of chemical research · 2017Review
- A new nonpolar N-hydroxy imidazoline lead compound with improved activity in a murine model of late-stage Trypanosoma brucei brucei infection is not cross-resistant with diamidines.Antimicrobial agents and chemotherapy · 2015Article
- In and out of the minor groove: interaction of an AT-rich DNA with the drug CD27.Acta crystallographica. Section D, Biological crystallography · 2014Article
- The structure of an authentic spore photoproduct lesion in DNA suggests a basis for recognition.Acta crystallographica. Section D, Biological crystallography · 2014Article
- Structure-based DNA-targeting strategies with small molecule ligands for drug discovery.Medicinal research reviews · 2013Review
- Minor groove to major groove, an unusual DNA sequence-dependent change in bend directionality by a distamycin dimer.Biochemistry · 2011Article
- Understanding the DNA binding of novel non-symmetrical guanidinium/2-aminoimidazolinium derivatives.Organic & biomolecular chemistry · 2010Article
- The many twists and turns of DNA: template, telomere, tool, and target.Current opinion in structural biology · 2010Review
- Semi-automated high-throughput fluorescent intercalator displacement-based discovery of cytotoxic DNA binding agents from a large compound library.Bioorganic & medicinal chemistry letters · 2010Article
Corrections and comments
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Authors and funding
7 authors at 5 institutions in 2 countries.
Funding
Abstract
The pursuit of small molecules that bind to DNA has led to the discovery of selective and potent antitrypanosomal agents, specifically 4,4'-bis(imidazolinylamino)- and 4,4'-bis(guanidino)diphenylamine compounds, CD27 and CD25, respectively. Although the antitrypanosomal properties of these compounds have been characterized, further development of this series of compounds requires assessment of their DNA site selectivities and affinities. Toward this end, both compounds have been analyzed and found to selectively bind AT sequences. However, CD27 was found to bind with higher affinity to 5'-AATT than 5'-ATAT while CD25 bound more weakly but equally well to either sequence. To detail the nature of its interactions with DNA, the crystal structure of CD27, bound to its preferred DNA-binding site 5'-AATT within a self-complementary oligonucleotide, 5'-d(CTTAATTCGAATTAAG), was determined at 1.75 A using a host-guest approach. Although CD27 is predicted to be highly twisted in its energy-minimized state, it adopts a more planar crescent shape when bound in the minor groove of the DNA. Interactions of CD27 with 5'-AATT include bifurcated hydrogen bonds, providing a basis for selectivity of this site, and favorable van der Waals interactions in a slightly widened minor groove. Thus, an induced fit results from conformational changes in both the ligand and the DNA. Our studies suggest a basis for understanding the mechanism of the antitrypanosomal activity of these symmetric diphenylamine compounds.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.