Synthesis and characterization of water-soluble free-base, zinc and copper porphyrin–oligonucleotide conjugates

Mammana, Angela; Asakawa, Tomohiro; Bitsch-Jensen, Klaus; Wolfe, Amanda L.; Chaturantabut, Saireudee; Otani, Yuko; Li, Xiaoxu; Li, Zengmin; Nakanishi, Koji; Baláž, Milan; Ellestad, George A.; Berova, Nina

doi:10.1016/j.bmc.2008.05.041

Cited by 38 publications

(26 citation statements)

References 30 publications

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“…UV -vis spectra of compound 1 showed typical spectrum for free base tetraaryl porphyrin derivative. Incorporation of zinc(II) ion into porphyrin during automatic DNA synthesis process was also reported by the other group (27). This is probably because nucleic acid bases near the porphyrin moiety might act as intermolecular catalyst for incorporation of zinc(II) in water existing in its very small amount.…”

Section: Resultsmentioning

confidence: 82%

Synthesis of oligo-DNA containing hydrophilic porphyrin in the main chain, and its energy transfer behaviour in duplex state

Ohya

Hashimoto

et al. 2009

Supramolecular Chemistry

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DNA is one of the best candidates as building blocks for bottom-up approach to nanometre size architecture in nanotechnology. In natural photosynthetic system, the arrangement of porphyrin derivatives with regulated distances, orders and orientations provides an efficient photon-energy collecting and transmission. We have studied about chromophore arrangement on DNA assembly as a simple artificial model of photosynthetic and photo-energy transmission systems. In order to prepare DNAs containing porphyrin residues at desired sites, a hydrophilic porphyrin amidite derivative, which can be utilised on automatic DNA synthesizer, was synthesised. The porphyrin amidite derivative was applied for automatic DNA synthesizer to give single-strand DNA (ssDNA) containing porphyrin set in the chain. The obtained ssDNA was mixed with complementary counter strand having another chromophore black hole quencher-3 (BHQ-3) to form duplex by selfassembly. The quenching behaviour by energy transfer from the porphyrin to BHQ-3 was monitored by fluorescence measurement.

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Section: Resultsmentioning

confidence: 82%

Synthesis of oligo-DNA containing hydrophilic porphyrin in the main chain, and its energy transfer behaviour in duplex state

Ohya

Hashimoto

et al. 2009

Supramolecular Chemistry

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“…[1][2][3] Synthesized earlier conjugates of macrocycles with polyamines, amino acids, peptides, peptidomimetics, antibiotics, nucleotides, carbohydrates, bile acids, lipids, steroids, etc., revealed prospective implications in biomedical studies and photodynamic therapy. [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19] In this study we have synthesized conjugates of pyropheophorbide a with androgen receptor ligandstestosterone and dihydrotestosterone. Аndrogen receptor is known to be an important drug target for treatment of prostate cancer.…”

Section: Conjugates Of Pyropheophorbide a With Androgen Receptor Ligandsmentioning

confidence: 99%

Conjugates of Pyropheophorbide a with Androgen Receptor Ligands

Zolottsev¹,

Zazulina²,

Morozevich³

et al. 2017

MHC

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“…The reaction product was filtrated out the reaction mixture and washed with dichloromethane, methanol, water, and methanol ( Fig. 1; catalysts [1][2][3][4][5][9][10][11] 15 .…”

Section: Methodsmentioning

confidence: 99%

Selective oxygenation of α-olefins by means of metalloporphyrin catalysts mimicking cytochrome P-450

Zachař

Petkova

Sýkora

et al. 2011

Collect. Czech. Chem. Commun.

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A significant problem associated with synthetic metalloporphyrin catalysts used to mimic oxygenation function of cytochrome P-450 is their deactivation due to the formation of inactive µ-oxo dimer. We prepared a series of porphyrin-based catalysts mimicking cytochrome P-450 potentially resistant to deactivation by varying the central metal ion, porphyrin ring substitution, and catalyst support. The influence of the nature of a solid support, the type of central cation and the chemical modification of the porphyrin ring on the catalytic efficiency was studied. The oxygenation ability of the synthesized catalysts was tested using 1-hexene as a substrate and tert-butyl hydroperoxide as an oxidant under various reaction conditions. Identification of the oxygenation products was performed with gas chromatography-mass spectrometry (GC-MS). Quantification of the products formed was based on GC with flame ionization detection (FID). It was found that the application of low GC injection temperature (150°C) was necessary to detect primary products of the oxygenation, peroxo alkenes, from which secondary oxygenation products, mainly epoxides, alcohols, aldehydes and ketones, were formed slowly. The efficiency of the individual catalysts depended on their structure and varied significantly. The most active catalysts were Fe(II)-tetraphenylporphyrin (TPP) immobilized on aminopolystyrene (aminoPS) and Mn(II)-TPP immobilized on aminoPS.

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Synthesis and characterization of water-soluble free-base, zinc and copper porphyrin–oligonucleotide conjugates

Cited by 38 publications

References 30 publications

Synthesis of oligo-DNA containing hydrophilic porphyrin in the main chain, and its energy transfer behaviour in duplex state

Synthesis of oligo-DNA containing hydrophilic porphyrin in the main chain, and its energy transfer behaviour in duplex state

Conjugates of Pyropheophorbide a with Androgen Receptor Ligands

Selective oxygenation of α-olefins by means of metalloporphyrin catalysts mimicking cytochrome P-450

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