title: Synthesis and hybridization properties of the conjugates of oligonucleotides and stabilization agents. Part 3.
abstract: New compounds having tri- or pentamethylenamine linker functions were synthesized. These derivatives were covalently attached through the 5'-phosphoramide linkage to heptanucleotide pd(CCAAACA). Complementary complexes of the octanucleotide pd(TGTTTGGC) and above oligonucleotide conjugates were tested for their thermodynamic response. The T(m) data and thermodynamic parameters for complex formation confirmed the ability of chromone (gamma-pyrone) derivatives to stabilize strongly the 7-mer/8-mer complementary complex. Moreover, benzochromone (naphthopyrane) and, surprisingly, tetrahydropyrimidinethanone derivatives showed the capacity of stabilizing this 7-mer/8-mer complementary complex. The effect of all these compounds on the stability of the oligonucleotide complexes (DeltaDeltaG at 37 degrees C ranged from -1.2 to -2.0 kcal/mol) was shown to be comparable to the effect of one nucleotide base pair and similar to the effect (DeltaDeltaG at 37 degrees C ranged from -1.5 to -2.0 kcal/mol) found for acridine-oligonucleotide conjugates, which served as a reference in this study.
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Viale Benedetto XV, 3-16132 Genova, Italy.
authors.forename: Enzo
authors.initials: E
authors.lastname: Sottofattori
authors.forename: Maria
authors.initials: M
authors.lastname: Anzaldi
authors.forename: Mauro
authors.initials: M
authors.lastname: Mazzei
authors.forename: Mariangela
authors.initials: M
authors.lastname: Miele
authors.forename: Alessandro
authors.initials: A
authors.lastname: Balbi
authors.forename: Dmitri S
authors.initials: DS
authors.lastname: Pyshnyi
authors.forename: Olga D
authors.initials: OD
authors.lastname: Zakharova
authors.forename: Tatyana V
authors.initials: TV
authors.lastname: Abramova
mesh_terms: D002851:Chromatography, High Pressure Liquid; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013816:Thermodynamics
chemical_list: D009841:Oligonucleotides