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| - Synthesis of Twisted Intercalating Nucleic Acids Possessing Acridine Derivatives.Thermal Stability Studies
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| - Twisted intercalating nucleic acids (TINA) possessing acridine derivatives have been synthesized via thepostsynthetic modifications of oligonucleotides possessing insertions of (R)-1-O-(4-iodobenzyl)glycerol (8) or(R)-1-O-(4-ethynylbenzyl)glycerol (9) at the 5‘-end or in the middle as a bulge. In the first postsynthetic step,oligonucleotides 8 and 9 on the CPG support were treated with a Sonogashira coupling reaction mixture containing9-chloro-2-ethynylacridine or 9-chloro-2-iodoacridine, respectively. After the postsynthetic step, treatment of theoligonucleotides with 32% aq ammonia or 50% ethanolic solution of tris(2-aminoethyl)amine led to the substitutionof chloride on acridine concurrent with deprotection of the bases and cleavage of the oligonucleotides from CPG.Molecular modeling of the parallel triplex with a bulged insertion of the monomer (R)-3-O-[4-(9-aminoacridin-2-ylethynyl)benzyl]glycerol in the triplex-forming oligonucleotide (TFO) showed that the acridine moiety wasstacking between the bases of the duplex, while phenyl was placed between the bases of the TFO. Thermaldenaturation studies and fluorescence properties of TINA-acridine oligonucleotide duplexes and triplexes arediscussed.
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