72083-62-6Relevant articles and documents
Modulation of DNA-polyamide interaction by β-alanine substitutions: A study of positional effects on binding affinity, kinetics and thermodynamics
Wang, Shuo,Wilson, W. David,Aston, Karl,Koeller, Kevin J.,Harris, G. Davis,Rath, Nigam P.,Bashkin, James K.
, p. 7523 - 7536 (2014)
Hairpin polyamides (PAs) are an important class of sequence-specific DNA minor groove binders, and frequently employ a flexible motif, β-alanine (β), to reduce the molecular rigidity to maintain the DNA recognition register. To better understand the diverse effects that β can have on DNA-PA binding affinity, selectivity, and especially kinetics, which have rarely been reported, we have initiated a detailed study for an eight-heterocyclic hairpin PA and its β derivatives with their cognate and mutant sequences. With these derivatives, all internal pyrroles of the parent PA are systematically substituted with single or double βs. A set of complementary experiments have been conducted to evaluate the molecular interactions in detail: UV-melting, biosensor-surface plasmon resonance, circular dichroism and isothermal titration calorimetry. The β substitutions generally weaken the binding affinities of these PAs with cognate DNA, and have large and diverse influences on PA binding kinetics in a position- and number-dependent manner. The DNA base mutations have also shown positional effects on the binding of a single PA. Besides the β substitutions, the monocationic Dp group [3-(dimethylamino)propylamine] in parent PA has been modified into a dicationic Ta group (3,3′-diamino-N-methyldipropylamine) to minimize the frequently observed PA aggregation with ITC experiments. The results clearly show that the Ta modification not only maintains the DNA binding mode and affinity of PA, but also significantly reduces PA aggregation and allows the complete thermodynamic signature of eight-ring hairpin PA to be determined for the first time. This combined set of results significantly extends our understanding of the energetic basis of specific DNA recognition by PAs.
Ortho -Fluoroazobenzene derivatives as DNA intercalators for photocontrol of DNA and nucleosome binding by visible light
Heinrich, Benedikt,Bouazoune, Karim,Wojcik, Matthias,Bakowsky, Udo,Vázquez, Olalla
supporting information, p. 1827 - 1833 (2019/02/20)
We report a high-affinity photoswitchable DNA binder, which displays different nucleosome-binding capacities upon visible-light irradiation. Both photochemical and DNA-recognition properties were examined by UV-Vis, HPLC, CD spectroscopy, NMR, FID assays,
Synthesis of pyrrole-imidazole polyamide oligomers based on a copper-catalyzed cross-coupling strategy
Shiga, Naoki,Takayanagi, Shihori,Muramoto, Risa,Murakami, Tasuku,Qin, Rui,Suzuki, Yuta,Shinohara, Ken-ichi,Kaneda, Atsushi,Nemoto, Tetsuhiro
supporting information, p. 2197 - 2200 (2017/04/27)
Pyrrole-imidazole (Py-Im) polyamides are useful tools for chemical biology and medicinal chemistry studies due to their unique binding properties to the minor groove of DNA. We developed a novel method of synthesizing Py-Im polyamide oligomers based on a Cu-catalyzed cross-coupling strategy. All four patterns of dimer fragments could be synthesized using a Cu-catalyzed Ullmann-type cross-coupling with easily prepared monomer units. Moreover, we demonstrated that pyrrole dimer, trimer, and tetramer building blocks for Py-Im polyamide synthesis were accessible by combining site selective iodination of the pyrrole/pyrrole coupling adduct.
