PMID: 9427534Jan 14, 1998Paper

A series of meso-tris (N-methyl-pyridiniumyl)-(4-alkylamidophenyl) porphyrins: synthesis, interaction with DNA and antibacterial activity

Biochimica Et Biophysica Acta
H LiL Czuchajowski

Abstract

A series of meso-5,10,15-tris(N-methyl-4-pyridiniumyl)-20-(4-alkylamidophen yl) porphyrins were synthesized by derivatizing the amino group on the phenyl ring with the following hydrophobic groups: -C(O)C7F15, -C(O)CH=CH2, C(O)CH3, -C(O)C7H15, and -C(O)C15H31. The cationic tris-pyridiumyl porphyrin core serves as a DNA binding motif and a photosensitizer to photomodify DNA molecules. The changes of the UV-Vis absorption spectra during the titration of these porphyrins with calf thymus DNA revealed a large bathochromic shift (up to 14 nm) and a hypochromicity (up to 55%) of the porphyrins Soret bands, usually considered as proof of porphyrin intercalation into DNA. Association constants (K) calculated according to the McGhee and von Hippel model, were in the range of 10(6)-10(7) M(-1). An increase in hydrophobicity of the substituents at the 20-meso-position produced higher binding affinity. These porphyrins caused photomodification of the supercoiled plasmid DNA when a green laser beam at 532 nm was applied. Those with higher surface activity acted more efficiently as DNA photomodifiers. The porphyrin with a perfluorinated alkyl chain (-COC7F15) at the meso-20-position inhibited the growth of gram-positive bacteria (S. aureus, ...Continue Reading

References

Jun 1, 1989·AIDS·M AsanakaY Kato
Nov 30, 1988·Biochemical and Biophysical Research Communications·E J GibbsR F Pasternack
May 10, 1983·Biochemistry·R F PasternackJ J Villafranca
Jan 18, 1994·Biochemistry·U SehlstedtJ C Dabrowiak
Mar 5, 1996·Biochemistry·L A LipscombL D Williams

❮ Previous
Next ❯

Citations

Nov 1, 2011·Applied Microbiology and Biotechnology·Eliana AlvesAdelaide Almeida
Jul 17, 2007·Biochemistry. Biokhimii︠a︡·M MonajjemiF Naderi
May 15, 2007·Bioinorganic Chemistry and Applications·Alexandra A KuznetsovaOlga S Fedorova
Nov 17, 2015·Journal of Medicinal Chemistry·José A González-DelgadoBruno Sarmento
Jun 5, 2013·Colloids and Surfaces. B, Biointerfaces·Zi-Qiang XuYi Liu
May 31, 2013·Bioorganic & Medicinal Chemistry·Eliana AlvesAdelaide Almeida
Aug 10, 2011·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Cátia ArrojadoAdelaide Almeida
Jan 1, 2007·Biochemistry and Molecular Biology Education : a Bimonthly Publication of the International Union of Biochemistry and Molecular Biology·Daniel A Caminos, Edgardo N Durantini
Jun 16, 2001·Rapid Communications in Mass Spectrometry : RCM·M R DominguesA J Ferrer-Correia
Mar 20, 2008·Chembiochem : a European Journal of Chemical Biology·Zhuo TangJörg S Hartig
Aug 30, 2008·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Daniel A CaminosEdgardo N Durantini
Jan 6, 2006·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Daniel A CaminosEdgardo N Durantini
Feb 20, 2014·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·M A PereiraA Almeida
May 24, 2005·FEMS Immunology and Medical Microbiology·Mariana B SpesiaEdgardo N Durantini
Jun 6, 2009·Photochemistry and Photobiology·Gunjan PandeySneha Sudha Komath
Mar 9, 2010·Proteomics·Vanya P BogoevaSabato D'Auria
Oct 31, 2001·European Journal of Biochemistry·R KenothM J Swamy
Mar 7, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Florent Le GuernVincent Sol

❮ Previous
Next ❯

Related Concepts

Related Feeds

Antifungals (ASM)

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.

Antifungals

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.