Interactions of DNA with a new electron-deficient tentacle porphyrin:meso-Tetrakis[2,3,5,6-tetrafluoro-4-(2-trimethylammoniumethylamine)phenyl]porphyrin

McClure, Julie E.; Baudouin, Lydie; Mansuy, Daniel; Marzillï, Luigi G.

doi:10.1002/(sici)1097-0282(199708)42:2<203::aid-bip9>3.0.co;2-r

Cited by 38 publications

(25 citation statements)

References 45 publications

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“…An intriguing addition to the porphyrin story are the "tentacle" porphyrins TθOPP and TθF4TAP, which are tetracationic but have the positive charges decoupled from the porphyrin by a fl exible spacer [61][62][63][64]. Both tentacle porphyrins readily assemble into stacked aggregates in the presence of DNA.…”

Section: Tentacle Porphyrinsmentioning

confidence: 58%

DNA-Templated Assembly of Helical Multichromophore Aggregates

Armitage¹

2005

Molecular and Supramolecular Photochemistry

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Section: Tentacle Porphyrinsmentioning

confidence: 58%

DNA-Templated Assembly of Helical Multichromophore Aggregates

Armitage¹

2005

Molecular and Supramolecular Photochemistry

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“…[40][41][42] Recent reports have shown that the relatively flexible and electron-rich tentacle porphyrins self-stack on the outside of DNA, with extensive self-stacking favored at high R values and at high salt concentrations and moderate self-stacking favored at intermediate R values and at low salt concentrations. [43][44][45] Viscosity Studies. Because there is still inadequate understanding of the relationship between CD spectra and binding mode, we conducted viscosity measurements (Supporting Information) with the [CH 3 Co(por)] 4+ cations.…”

Section: Discussionmentioning

confidence: 99%

Synthesis and DNA Binding of Novel Water-Soluble Cationic Methylcobalt Porphyrins

Trommel

Marzillï

2001

Inorg. Chem.

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Organocobalt derivatives of tetracationic water-soluble porphyrins are difficult to prepare via the typical reductive alkylation of the Co(II)(por) (porH(2) = porphyrin ligand). None have been reported. The problem may arise because the porphyrin core is made relatively electron poor by the positively charged peripheral groups. We have circumvented this problem by using the [Co(III)(NH(3))(5)CH(3)](2+) reagent, which inserts the Co(III)-CH(3) moiety directly into porH(2) in water under basic conditions. The method afforded two new [CH(3)Co(por)](4+) derivatives, [CH(3)CoTMpyP(4)](4+) and [CH(3)CoTMAP](4+), where [TMpyP(4)](4+) and [TMAP](4+) are the coordinated, NH-deprotonated forms of meso-tetrakis(N-methyl-4-pyridiniumyl)porphyrin and meso-tetrakis(N,N,N-trimethylaniliniumyl)porphyrin, respectively. The binding of the two new [CH(3)Co(por)](4+) cations to DNA and to the synthetic DNA polymers [poly(dA-dT)](2) and [poly(dG-dC)](2) was studied. Using published criteria by which changes in DNA viscosity and in the visible and CD spectra in the Soret region can be used to assess DNA binding, we conclude that both are outside binders. A large hypochromicity of the Soret bands of the [CH(3)Co(por)](4+) cations observed upon outside binding to DNA may indicate a high degree of self-stacking. The visible absorption and CD spectra of the [CH(3)Co(por)](4+) cations in the presence of 1:1 mixtures of [poly(dA-dT)](2) and [poly(dG-dC)](2) are nearly identical to those with [poly(dA-dT)](2) alone and are very different from those of [poly(dG-dC)](2) alone. Thus, both cations show a high preference for outside binding at AT-rich over GC-rich DNA sites. Upon binding of each of the [CH(3)Co(por)](4+) cations to all of the DNA polymers, the Soret bands exhibit blue shifts, whereas the Soret bands of the corresponding [(H(2)O)(2)Co(por)](5+) cations exhibit red shifts. The blue shifts strongly suggest that the [CH(3)Co(por)](4+) cations, particularly [CH(3)CoTMAP](4+), become five-coordinate forms to some extent on DNA binding; this result is the first good evidence for the presence at equilibrium of five-coordinate CH(3)Co(III)(N(4)) forms in water.

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“…In the studies of porphyrin-DNA interaction, three major binding modes have been proposed for the DNA binding of cationic porphyrins: intercalation, outside groove binding, and outside binding with self-stacking in which porphyrins are stacked along the DNA helix [13][14][15][16]. In addition to the experimental conditions such as pH, ionic strength and molar ratio of porphyrin to DNA base pair [13,16,[17][18][19], the nature of porphyrins plays an important role in their binding to DNA.…”

Section: Introductionmentioning

confidence: 99%

“…In addition to the experimental conditions such as pH, ionic strength and molar ratio of porphyrin to DNA base pair [13,16,[17][18][19], the nature of porphyrins plays an important role in their binding to DNA. meso-tetrakis(N-methylpyridinium-4-yl)porphyrin (H 2 TMPyP) and its derivatives as well as their metal complexes are well-known as cationic porphyrins with six-membered rings at the meso-position and have been intensively studied over the past decades [1][2][3][4][5][6][7][8][9][10][11][12].…”

Section: Introductionmentioning

confidence: 99%

Binding of nickel(II) tetrakis(dimethylpyrazolium-4-yl)porphyrin to poly(dG-dC)₂ and poly(dA-dT)₂

Tjahjono

Suhendar

Permana

et al. 2010

J. Porphyrins Phthalocyanines

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The interaction of nickel(II) complex of cationic porphyrins bearing fi ve-membered rings, meso-tetrakis (1,2-dimethylpyrazolium-4-yl)porphyrinatonickel(II) (NiPzP), with synthetic polynucleotides poly(dG-dC) 2 and poly(dA-dT) 2 has been characterized by viscometric, visible absorption, CD and MCD spectroscopic, and melting temperature measurements. The nickel(II) complex NiPzP is intercalated into poly(dG-dC) 2 but outside bound to the major groove of poly(dA-dT) 2 . The binding constants of NiPzP to poly(dG-dC) 2 and poly(dA-dT) 2 are in the order of 10 6 M -1 and comparable to those of other reported cationic metalloporphyrins. The binding process of NiPzP to poly(dG-dC) 2 and poly(dA-dT) 2 is endothermic and entropically driven.KEYWORDS: metallopyrazolium-4-ylporphyrin, poly(dG-dC) 2 , poly(dA-dT) 2 , porphyrin-DNA interaction, thermodynamic parameters. SPP full member in good standing *Correspondence to: Daryono H. Tjahjono, email: daryonohadi@fa.itb.ac.id, fax: +62 22-250-4842 and Hidenari Inoue, email: inoue@applc.keio.ac.jp, fax: +81 45-566-1551 J. Porphyrins Phthalocyanines 2010.14:305-313. Downloaded from www.worldscientific.com by SIMON FRASER UNIVERSITY on 02/02/15. For personal use only.

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Interactions of DNA with a new electron-deficient tentacle porphyrin:meso-Tetrakis[2,3,5,6-tetrafluoro-4-(2-trimethylammoniumethylamine)phenyl]porphyrin

Cited by 38 publications

References 45 publications

DNA-Templated Assembly of Helical Multichromophore Aggregates

DNA-Templated Assembly of Helical Multichromophore Aggregates

Synthesis and DNA Binding of Novel Water-Soluble Cationic Methylcobalt Porphyrins

Binding of nickel(II) tetrakis(dimethylpyrazolium-4-yl)porphyrin to poly(dG-dC)₂ and poly(dA-dT)₂

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Interactions of DNA with a new electron-deficient tentacle porphyrin:meso-Tetrakis[2,3,5,6-tetrafluoro-4-(2-trimethylammoniumethylamine)phenyl]porphyrin

Cited by 38 publications

References 45 publications

DNA-Templated Assembly of Helical Multichromophore Aggregates

DNA-Templated Assembly of Helical Multichromophore Aggregates

Synthesis and DNA Binding of Novel Water-Soluble Cationic Methylcobalt Porphyrins

Binding of nickel(II) tetrakis(dimethylpyrazolium-4-yl)porphyrin to poly(dG-dC)2 and poly(dA-dT)2

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Binding of nickel(II) tetrakis(dimethylpyrazolium-4-yl)porphyrin to poly(dG-dC)₂ and poly(dA-dT)₂