DNA-tentacle porphyrin interactions: AT over GC selectivity exhibited by an outside binding self-stacking porphyrin

Mukundan, Nancy E.; Pethő, Gábor; Dixon, Dabney W.; Marzillï, Luigi G.

doi:10.1021/ic00118a015

Cited by 84 publications

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“…Enormous enhancement of binding in the presence of Cu(II) would be due to the cooperative self-stacking of the dimers. Although several DNA ligands that aggregate on DNA are known [41][42][43][44], the aggregate presented in this paper is unique in its reversible formation and structural homogeneity. Further, the system can be also applied to constructing well-defined 1D nanostructures or 1D arrays of metal ions; that is, polynuclear nanostructures [45][46][47].…”

Section: Discussionmentioning

confidence: 99%

Metal ion-directed cooperative DNA binding of small molecules

Ihara

Ikegami

Fujii

et al. 2006

Journal of Inorganic Biochemistry

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Section: Discussionmentioning

confidence: 99%

Metal ion-directed cooperative DNA binding of small molecules

Ihara

Ikegami

Fujii

et al. 2006

Journal of Inorganic Biochemistry

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“…Similar spectral behavior was observed in the binding of TQOPP (meso-tetrakis [4-[(3-(trimethylammonio)propyl)-oxy]phenyl]porphine), which has long periphery substituents. 26,27 Generally, porphyrins show a monomeric CD band in the Soret band region at a low mixing ratio, regardless of their periphery substituents or the existence of a central metal; a weak negative band for intercalation or a strong positive one for external binding along the DNA groove. There are two possibilities for the unusual bisignate CD band at a low mixing ratio; one being from the abnormal binding angle of B-TMPyP to the DNA helix axis.…”

Section: Discussionmentioning

confidence: 99%

Direct Stacking of Non-metallic Planar Porphyrin to DNA

2008

Bulletin of the Korean Chemical Society

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Porphyrins generally bind DNA in two different ways with respect to the mixing ratio; monomeric binding at a low mixing ratio and outside stacking at a high mixing ratio. In the present study, CTDNA binding property of a planar structured porphyrin, 5,10,15,20-tetrakis(N-methyl-4-pyridin-4-yl-phenyl)porphyrin (referred to as B-TMPyP) was investigated using absorption, CD, LD, and LD r spectroscopies. B-TMPyP produced a bisignate CD band, even at the lowest mixing ratio, indicating that B-TMPyP may not have a monomeric binding mode. From the observations of the spectral changes to the absorption, CD, and LD spectra in mixing ratio dependent titrations, B-TMPyP seems to have a quite different stacking type compared to that for the binding of H2TMPyP. Moreover, B-TMPyP produced a CD band of opposite shape in the Soret band region. A qualitative explanation for the observed optical differences is also given.

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“…8,[41][42][43][44] Therefore, the characterization in the solution state of these cationic bis-porphyrins was first done by visible spectrometry. The value of the e ).…”

Section: Discussionmentioning

confidence: 99%

Solution Properties and Photonuclease Activity of Cationic Bis-porphyrins Linked with a Series of Aliphatic Diamines.

Yamakawa

Ishikawa

Uno

2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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The development of efficient photo-induced DNA cleavage agents has been of particular interest for biomedical applications such as cancer photodynamic therapy (PDT). Toward this objective, we synthesized a series of cationic bis-porphyrins with various lengths of diamino alkyl linkage, N,N-bis{4-[10,15,20-tris(1-methylpyridinium-4-yl)porphyrin-5-yl]benzoyl}oligomethylenediamine hexaiodide. They were expected to show more efficient photocleavage of DNA than unichromophore meso-tetrakis(4-N-methylpyridiniumyl)porphine (TMPyP), which is well known to cleave DNA effectively on illumination. The cationic bis-porphyrins were found to self-aggregate in aqueous solution, and the aggregation property was accounted for by the formation of an intermolecular dimer. Because conservative-type circular dichroism spectra of the bis-porphyrins were induced in the Soret region on binding to calf thymus DNA, we assigned their binding mode to outside self-stacking on the DNA surface. Their photonuclease activity using plasmid DNA decreased as the number of their linker hydrocarbons increased, and was well correlated with their tendency for dimerization. The inhibitory effect of azide anion, N 3 ؊ , and the enhancement effect of D 2 O suggest that singlet oxygen was probably involved in the photocleavage of DNA.Key words porphyrin; DNA; photocleavage; aggregation; singlet oxygen plex DNA, and photonuclease activity. We show that these cationic bis-porphyrins formed intermolecular dimers in aqueous solution, and bound to calf thymus DNA (CTDNA) with outside self-stacking. Their photocleavage efficiency of plasmid DNA diminished as the number of their linker hydrocarbons increased, and correlated with their tendency for dimerization. ExperimentalInstrumentation The 1 H-NMR spectra were recorded on a JEOL GX-400 or JNM-A-500 spectrometer. The MALDI-TOF (matrix-assisted laser desorption/ionization time-of-flight) mass spectra (MS) were measured on a Bruker REFLEX TM . The UV-visible absorption measurement was performed on a Beckman DU650 spectrophotometer. The CD spectra were recorded on a JASCO J-720 spectropolarimeter. Elemental analyses were performed at the Analytical Center, Kumamoto University. Materials and MethodsReagents for the synthesis of cationic bis-porphyrins were purchased from Tokyo Kasei Chemical Co. Thionyl chloride was distilled before use. Hexane, methylene chloride, and triethylamine were distilled in the presence of P 2 O 5 .24) 5-(4-methoxycarbonylphenyl)-10,15,20-tris(4-pyridyl)porphine (TPyPCOOCH 3 ) and 5-(4-carboxyphenyl)-10,15,20-tris(4-pyridyl)porphine (TPyPCOOH) were synthesized according to the previous method.25) CTDNA was purchased from Sigma Chemical Co., and the solution was quantitated spectrophotometrically using e 260 ϭ13200 M (base pairs) Ϫ1 · cm Ϫ1 . The tosylate salt of TMPyP was purchased from Dojin Chemical Co.General Procedure for the Synthesis of Non-charged Bis-porphyrins Linked with a Series of Aliphatic Diamines TPyPCOOH (250 mg, 0.378 mmol) was dissolved in 35 ml of thionyl chloride unde...

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DNA-tentacle porphyrin interactions: AT over GC selectivity exhibited by an outside binding self-stacking porphyrin

Cited by 84 publications

References 0 publications

Metal ion-directed cooperative DNA binding of small molecules

Metal ion-directed cooperative DNA binding of small molecules

Direct Stacking of Non-metallic Planar Porphyrin to DNA

Solution Properties and Photonuclease Activity of Cationic Bis-porphyrins Linked with a Series of Aliphatic Diamines.

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