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Recognition of the DNA minor groove by thiazotropsin analogues.

Alniss HY, Salvia MV, Sadikov M, Golovchenko I, Anthony NG, Khalaf AI, MacKay SP, Suckling CJ, Parkinson JA
Chembiochem 15 1978-90 (2014)
Related entries: 2mnb, 2mnd, 2mne

Cited: 8 times
EuropePMC logo PMID: 25045155

Abstract

Solution-phase self-association characteristics and DNA molecular-recognition properties are reported for three close analogues of minor-groove-binding ligands from the thiazotropsin class of lexitropsin molecules; they incorporate isopropyl thiazole as a lipophilic building block. Thiazotropsin B (AcImPy(iPr) ThDp) shows similar self-assembly characteristics to thiazotropsin A (FoPyPy(iPr) ThDp), although it is engineered, by incorporation of imidazole in place of N-methyl pyrrole, to swap its DNA recognition target from 5'-ACTAGT-3' to 5'-ACGCGT-3'. Replacement of the formamide head group in thiazotropsin A by nicotinamide in AIK-18/51 results in a measureable difference in solution-phase self-assembly character and substantially enhanced DNA association characteristics. The structures and associated thermodynamic parameters of self-assembled ligand aggregates and their complexes with their respective DNA targets are considered in the context of cluster targeting of DNA by minor-groove complexes.

Reviews citing this publication (1)

  1. An overview of recent advances in duplex DNA recognition by small molecules. Bhaduri S, Ranjan N, Arya DP. Beilstein J Org Chem 14 1051-1086 (2018)

Articles citing this publication (7)

  1. Imino proton NMR guides the reprogramming of A•T specific minor groove binders for mixed base pair recognition. Harika NK, Paul A, Stroeva E, Chai Y, Boykin DW, Germann MW, Wilson WD. Nucleic Acids Res 44 4519-4527 (2016)
  2. Structural basis of DNA duplex distortion induced by thiazole-containing hairpin polyamides. Padroni G, Parkinson JA, Fox KR, Burley GA. Nucleic Acids Res 46 42-53 (2018)
  3. Structural and Kinetic Profiling of Allosteric Modulation of Duplex DNA Induced by DNA-Binding Polyamide Analogues. Aman K, Padroni G, Parkinson JA, Welte T, Burley GA. Chemistry 25 2757-2763 (2019)
  4. Novel Pyridazin-3(2H)-one-Based Guanidine Derivatives as Potential DNA Minor Groove Binders with Anticancer Activity. Costas-Lago MC, Vila N, Rahman A, Besada P, Rozas I, Brea J, Loza MI, González-Romero E, Terán C. ACS Med Chem Lett 13 463-469 (2022)
  5. Hidden entropic contribution in the thermodynamics of molecular complexation. Evstigneev MP, Lantushenko AO, Golovchenko IV. Phys Chem Chem Phys 18 7617-7625 (2016)
  6. Synthesis of 5-Alkyl- and 5-Phenylamino-Substituted Azothiazole Dyes with Solvatochromic and DNA-Binding Properties. Pithan PM, Kuhlmann C, Engelhard C, Ihmels H. Chemistry 25 16088-16098 (2019)
  7. Synthesis and Evaluation of Novel DNA Minor Groove Binders as Antiamoebic Agents. Alniss HY, Khan NA, Boghossian A, Akbar N, Al-Jubeh HM, Msallam YA, Saeed BQ, Siddiqui R. Antibiotics (Basel) 11 935 (2022)


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