Interaction of cationic porphyrins with DNA: Importance of the number and position of the charges and minimum structural requirements for intercalation

Journal Article · Tue May 01 00:00:00 EDT 1990 · Biochemistry; (USA)

DOI:https://doi.org/10.1021/bi00469a025· OSTI ID:6323167

Sari, M A; Battioni, J P; Dupre, D; Mansuy, D ^[1]; Le Pecq, J B ^[2]

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1. Universite Rene Descartes, Paris (France)
2. Institut Gustave Roussy, Villejuif (France)

Thirty-three porphyrins or metalloporphyrins corresponding to the general formula (meso-(N-methyl-4(or 3 or 2)-pyridiniumyl){sub n}(aryl){sub 4-n}porphyrin)M (M = H{sub 2}, Cu{sup II}, or ClFe{sup III}), with n = 2-4, have been synthesized and characterized by UV-visible and {sup 1}H NMR spectroscopy and mass spectrometry. These porphyrins differ not only in the number (2-4) and position of their cationic charges but also in the steric requirements to reach even temporarily a completely planar geometry. Interaction of these porphyrins or metalloporphyrins with calf thymus DNA has been studied and their apparent affinity binding constants have been determined by use of a competition method with ethidium bromide which was applicable not only for all the free base porphyrins but also for their copper (II) or iron (III) complexes. Whatever their mode of binding may be, their apparent affinity binding constants were relatively high and a linear decrease of log K{sub app} with the number of porphyrin charges was observed. Studies of porphyrin-DNA interactions by UV and fluorescence spectroscopy, viscosimetry, and fluorescence energy transfer experiments showed that not only the tetracationic meso-tetrakis(N-methyl-4(or 3)-pyridiniumyl)porphyrins, which both involved four freely rotating meso-aryl groups, but also the corresponding tri- and dicationic porphyrins were able to intercalate into calf thymus DNA. These results show that only half of the porphyrin ring is necessary for intercalation to occur.

• OSTI ID: 6323167
• Journal Information: Biochemistry; (USA), Journal Name: Biochemistry; (USA) Vol. 29:17; ISSN 0006-2960; ISSN BICHA
• Country of Publication: United States
• Language: English

Related Subjects

550601* -- Medicine-- Unsealed Radionuclides in Diagnostics
62 RADIOLOGY AND NUCLEAR MEDICINE
ANIMALS
BARYONS
BIOSYNTHESIS
BODY
CALVES
CARBOXYLIC ACIDS
CATTLE
CHEMICAL REACTIONS
CLATHRATES
CROSS-LINKING
DNA
DOMESTIC ANIMALS
ELEMENTARY PARTICLES
EMISSION SPECTRA
FERMIONS
FLUORESCENCE
GEOMETRY
HADRONS
HETEROCYCLIC ACIDS
HETEROCYCLIC COMPOUNDS
LUMINESCENCE
LYMPHATIC SYSTEM
MAGNETIC RESONANCE
MAMMALS
MASS SPECTROSCOPY
MATHEMATICS
NMR SPECTRA
NUCLEAR MAGNETIC RESONANCE
NUCLEIC ACIDS
NUCLEONS
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANS
POLYMERIZATION
PORPHYRINS
PROTONS
RESONANCE
RUMINANTS
SPECTRA
SPECTROSCOPY
SYNTHESIS
THYMUS
VERTEBRATES