DNA sequence-specific ligands. XVIII. Synthesis, physico-chemical properties; genetic, virological, and biochemical studies of fluorescent dimeric bisbenzimidazoles DBPA(n)

Dimeric Bis-Benzimidazole-Pyrroles DB2Py(n) – AT-Site-Specific Ligands: Synthesis, Physicochemical Analysis, and Biological Activity

“…Earlier, we obtained Hoechst 33258 -based fluorescent water-soluble AT-specific dimeric bis-benzimidazole DNA narrow-groove-binding ligands of the DB(n) , DBP(n) , DBA(n), and DBPA(n) series, where n is equal to the number of methylene links in the linker. All the above-mentioned compounds contained two AT-recognizing fragments in their structure, consisting of two bis-benzimidazole units [ 5 , 6 , 7 , 8 ]. Upon interaction with DNA, each AT-recognizing fragment formed a bifurcation (three-center) hydrogen bond with an O 2 thymine atom and/or an adenine atom of two neighboring AT pairs, while covering a region of approximately one and a half base pairs [ 9 ].…”

“…Ранее мы получили на основе Hoechst 33258 ряд флуоресцентных водорастворимых АТспецифичных димерных бисбензимидазольных узкобороздочных лигандов серий DB(n), DBP(n), DBA(n) и DBPA(n), где n равно количеству метиленовых звеньев в линкере. Все вышеупомянутые соединения содержат в своей структуре два АТраспознающих фрагмента, состоящих из двух бис-бензимидазольных блоков [5][6][7][8]. При взаимодействии с ДНК каждый АТ-распознающий фрагмент образует бифуркационную (трехцентровую) водородную связь с О2-атомом тимина и/или N3-атомом аденина двух соседних AT-пар, накрывая при этом участок размером примерно полторы пары оснований [9].…”

DNA sequence-specific ligands. XX. Synthesis, spectral properties, virological and biochemical studies of fluorescent dimeric trisbenzimidazoles DB3P(n)

“…Previously we described the design and synthesis of several sets of dimeric bisbenzimidazoles [12][13][14][15][16][17], analogues of the dimeric bisbenzimidazole motif of the uorescent AT-speci c Hoechst 33258 dye. These dimeric bisbenzimidazoles were synthesized with the goal of developing AT speci c ligands noncovalently binding to the dsDNA minor groove and occupying nearly one coil.…”

“…These dimeric molecules can bind to two sites, each consisting of two AT pairs separated by two or more nucleotide pairs. Dimeric bisbenzimidazoles were shown to be effective agents in biochemical, virological, and genetic studies [12][13][14][15][16][17].…”