Joint molecular modeling and spectroscopic studies of DNA complexes of a bis(arginyl) conjugate of a tricationic porphyrin designed to target the major groove

Biochemistry
S MohammadiE Taillandier

Abstract

To target selectively the major groove of double-stranded B DNA, we have designed and synthesized a bis(arginyl) conjugate of a tricationic porphyrin (BAP). Its binding energies with a series of double-stranded dodecanucleotides, having in common a central d(CpG)2 intercalation site were compared. The theoretical results indicated a significant energy preference favoring major groove over minor groove binding and a preferential binding to a sequence encompassing the palindrome GGCGCC encountered in the Primary Binding Site of the HIV-1 retrovirus. Spectroscopic studies were carried out on the complexes of BAP with poly(dG-dC) and poly(dA-dT) and a series of oligonucleotide duplexes having either a GGCGCC, CCCGGG, or TACGTA sequence. The results of UV-visible and circular dichroism spectroscopies indicated that intercalation of the porphyrin takes place in poly(dG-dC) and all the oligonucleotides. Thermal denaturation studies showed that BAP increased significantly the melting temperature of the oligonucleotides having the GGCGCC sequence, whereas it produced only a negligible stabilization of sequences having CCCGGG or TACGTA in place of GGCGCC. This indicates a preferential binding of BAP to GGCGCC, fully consistent with the t...Continue Reading

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Citations

Apr 18, 2002·Biosensors & Bioelectronics·Brandy J White, H James Harmon
Nov 17, 2001·Bioorganic & Medicinal Chemistry·H OkadaY Uemori
Apr 26, 2003·Bioorganic & Medicinal Chemistry·Jeffrey A Turk, David B Smithrud
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Apr 23, 2013·Biophysical Chemistry·Adám OroszGabriella Csík
Mar 16, 2011·Biophysical Chemistry·Gábor MezoGabriella Csík
Nov 3, 2009·Bioorganic & Medicinal Chemistry·Lucie GuetzoyanJean-Pierre Mahy
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Feb 14, 2008·Bioconjugate Chemistry·Martha Sibrian-VazquezM Graça H Vicente

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