Efficient and easy synthesis of octathymidylate covalently linked to intercalating 9-aminoellipticine.
Reductive amination of 3'-apurinic octathymidylate with 9-aminoellipticine provides octathymidylate covalently linked to intercalating ellipticine through a 3,4-dihydroxypentamethylene linker. Studies of its binding properties to poly(rA) reveals the formation of two different complexes depending of the temperature (Tm 13 degrees C and 38 degrees C) with dT/rA stoichiometry respectively equal to 2/1 and 1/1. When compared to parent octathymidylate, stability of the latter duplex is enhanced by the interaction energy provided by the dye moiety.
Vasseur
J J
JJ
Laboratoire de Chimie Bio-Organique, UA 488 CNRS, Université des Sciences et Techniques du Languedoc, Montpellier, France.
Gauthier
C
C
Rayner
B
B
Paoletti
J
J
Imbach
J L
JL
D000470:Alkaloids / Q000138:chemical synthesis*; D004611:Ellipticines / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007364:Intercalating Agents; D009691:Nucleic Acid Denaturation; D011061:Poly A; D013816:Thermodynamics; D013938:Thymidine Monophosphate
D000470:Alkaloids; D004611:Ellipticines; D007202:Indicators and Reagents; D007364:Intercalating Agents; C055583:octathymidylate-9-aminoellipticine; D011061:Poly A; D013938:Thymidine Monophosphate