Acid–base properties and DNA-binding of water soluble N-confused porphyrins with cationic side-arms

Ikawa, Yoshiya; Moriyama, Shoji; Harada, Hiroyuki; Furuta, Hiroyuki

doi:10.1039/b810171j

Cited by 32 publications

(27 citation statements)

References 49 publications

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“…To investigate interactions between porphyrins and group I ribozymes, we employed meso -tetraarylporphyrins ( Figure 1 ) as a core platform structure because they have been used frequently in designing porphyrin-based functional molecules [ 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 ]. In this study, we primarily used pPyP and pPyNCP ( Figure 1 ) [ 23 , 28 ]. pPyP and pPyNCP have been shown to interact with various forms of DNA molecules, including single- and double-stranded DNAs [ 23 , 28 ].…”

Section: Resultsmentioning

confidence: 99%

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Modulation of Group I Ribozyme Activity by Cationic Porphyrins

Matsumura

Ito

Tanaka

et al. 2015

Biology

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The effects of cationic porphyrins on the catalytic activities of four group I ribozymes were investigated. A cationic porphyrin possessing four pyridinium moieties (pPyP) inhibited two group IC3 ribozymes (Syn Rz and Azo Rz) and a group IC1 ribozyme (Tet Rz). In the case of a group IA2 ribozyme (Td Rz), however, pPyP served not only as an inhibitor but also as an activator, and the effects of pPyP were dependent on its concentration. To analyze the structural and electronic factors determining the effects of pPyP on group I ribozymes, three cationic porphyrins (pPyNCP, pPyF4P, and TMPyP) were also examined. As interactions between small organic molecules and nucleic acids are attractive and important issues in biochemistry and biotechnology, this study contributes to the development of porphyrin-based molecules that can modulate functions of structured RNA molecules.

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Section: Resultsmentioning

confidence: 99%

“…Chemical syntheses of pPyP and pPyNCP were reported previously [ 23 ]. TMPyP was purchased from Sigma-Aldrich (St.…”

Section: Methodsmentioning

confidence: 99%

Modulation of Group I Ribozyme Activity by Cationic Porphyrins

Matsumura

Ito

Tanaka

et al. 2015

Biology

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“…[13,14] Watersoluble derivatives of 5,10,15,20-tetrakis(4'-sulfophenyl) porphyrin Investigations of inverted porphyrins properties, including aqueous media, have been carried out since their discovery due to the unique structure of these compounds. [15][16][17][18][19][20][21][22][23][24][25] Previously it was shown that diprotonated inverted platform possesses the properties of anionic receptor, [8,26] the zwitterions H 4 IP 2+ (PhSO 3 -) 4 and H 3 MeIP 2+ (PhSO 3 -) 4 are able to form supramolecular J-aggregates, stable in pHneutral aqueous solutions. [21,27] In this work we presented the results of theoretical and experimental studies of…”

Section: Introductionmentioning

confidence: 99%

Features of Inverted Tetrasulfophenylporphyrin Protonation. Crucial Role of Hydrogen Bonds

Sheinin¹,

Kulikova²,

Койфман³

2018

MHC

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Diprotonation equilibria of inverted platform of tetraanionic 5,10,15,20-tetrakis(4′-sulfophenyl)-2-aza-21carbaporphyrin, H 2 IP(PhSO 3 H) 4 , with perchloric acid in water was studied using DFT/B3LYP/6-31++G(d,p) and spectropotentiometric titration methods. In aqueous solution this porphyrinoid exists in the form of NH tautomer H 2 I (i) P(PhSO 3-) 4 with an inverted pyrrolenine ring, which is stabilized by bifurcated intramolecular hydrogen bonds between two pyrrole hydrogens and one pyrrolenine nitrogen. Intramolecular hydrogen bonds protect intramolecular hydrogen-bonding sites from intermolecular interactions. For this reason, the external nitrogen atom is protonated first, and then the internal one is protonated. The second proton switches the intramolecular hydrogen bonds to intermolecular hydrogen bonds. Diprotonated platform H 4 IP 2+ (PhSO 3-) 4 has the geometry of elastic 1,3-alternate, which is a molecular and anionic receptor. The equilibrium of the second stage protonation in water is completely shifted to the aquacomplex [H 4 IP 2+ (PhSO 3-) 4 ](H 2 O) 2 , which is formed due to the hydrogen and electrostatic binding of the solvent molecules on both receptor sites. Aquacomplex [H 4 IP ++ (PhSO 3-) 4 ](H 2 O) 2 is a monomer of linear J-aggregates self-assembly. The driving force of J-aggregates assembly is the formation of stronger anionic complexes as a result of water molecules intermolecular replacement by sulfonate groups of monomers.

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“…Biological applications of N-confused porphyrins are an intriguing and still less explored area. It has been observed that cationic N-confused porphyrin derivatives can bind to DNA [26] or stabilize G-quardruplex DNA [27]. N-confused porphyrins have also been proved efficient photosensitizer against breast adenocarcinoma cells [25].…”

Section: Introductionmentioning

confidence: 99%

The magnetic properties, DNA/HSA binding and nuclease activity of manganese N-confused porphyrin

Peng

Ali

et al. 2016

J. Porphyrins Phthalocyanines

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The first oxidative cleavage of DNA by manganese N-confused porphyrin [chloro(2aza-2-methyl-5,10,15,20-tetrakis(p-chlorophenyl)-21-carbaporphyrin)manganese(III), 1] using H 2 O 2 as oxidant agent and its magnetic, calf thymus DNA(ct-DNA)-and human serum albumin (HSA) binding properties were investigated. The magnitude of the axial (D) zero-field splitting for the mononuclear Mn(III) center in 1 was determined to be approximately 2.71 cm -1 by paramagnetic susceptibility measurements. The DNA-and HSA binding experimental results showed that 1 bound to ct-DNA via an outside groove binding mode and the hydrophobic cavity located in subdomain IIA of HSA with the binding constant of 4.144 × 10 5 M -1 and ~10 6 M -1 , respectively. Thermodynamic parameters revealed that both DNA-and HSA binding were spontaneous process. The main driven forces were the hydrogen bond and van der Waals for the former, but hydrophobic interaction for the latter, which were further confirmed by molecular docking modeling. Manganese N-confused porphyrin 1 could cleave the supercoiled plasmid DNA efficiently in the presence of hydrogen peroxide. Hydroxyl radical ( · OH) was found the active species for oxidative damage of DNA.

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Acid–base properties and DNA-binding of water soluble N-confused porphyrins with cationic side-arms

Cited by 32 publications

References 49 publications

Modulation of Group I Ribozyme Activity by Cationic Porphyrins

Modulation of Group I Ribozyme Activity by Cationic Porphyrins

Features of Inverted Tetrasulfophenylporphyrin Protonation. Crucial Role of Hydrogen Bonds

The magnetic properties, DNA/HSA binding and nuclease activity of manganese N-confused porphyrin

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