title: Application of Cu(I)-catalyzed azide-alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double-stranded DNA.
abstract: Efficient protocols based on Cu(I)-catalyzed azide-alkyne cycloaddition were developed for the synthesis of conjugates of pyrrole-imidazole polyamide minor groove binders (MGB) with fluorophores and with triplex-forming oligonucleotides (TFOs). Diverse bifunctional linkers were synthesized and used for the insertion of terminal azides or alkynes into TFOs and MGBs. The formation of stable triple helices by TFO-MGB conjugates was evaluated by gel-shift experiments. The presence of MGB in these conjugates did not affect the binding parameters (affinity and triplex stability) of the parent TFOs.
authors: Institute of Chemical Biology & Fundamental Medicine, SB of RAS, pr. Lavrent'eva 8, 630090 Novosibirsk, Russia.
authors: Svetlana V
authors: SV
authors: Vasilyeva
authors: Institute of Fundamental Sciences, Massey University, Private Bag 11-222, 4442 Palmerston North, New Zealand.
authors: Vyacheslav V
authors: VV
authors: Filichev
authors: Structure and Instability of Genomes, Sorbonne Universités, Muséum National d'Histoire Naturelle, INSERM U 1154, CNRS UMR 7196, 57 rue Cuvier, C.P. 26, 75231 Paris cedex 05, France.
authors: Alexandre S
authors: AS
authors: Boutorine
keywords: Cu(I)-catalyzed azide–alkyne cycloaddition; binding affinity; click chemistry; pyrrole–imidazole polyamides; sequence specificity: DNA; triplex-forming oligonucleotides