ChemInform Abstract: Synthesis of Tetraphenylporphyrins Under very Mild Conditions.

Lindsey, Jonathan S.; Hsu, Henry C.; Schreiman, Irwin C.

doi:10.1002/chin.198711289

Cited by 2 publications

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“…The standard Adler, 28 Lindsey, 29 and gas phase 30 methods of porphyrin synthesis result in low or erratic yields when the aldehyde bears highly polar or charged groups such as alcohols, thiols, carboxylic acids, pyridinium, and quaternary ammonium moieties. Therefore the starting aryl aldehydes bearing the methyl protected precursors of the above groups were used in the Adler synthesis of combinatorial libraries L, L1, L2, L3-libraries of 1540, 120, 120, and 21 porphyrins, respectively.…”

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Combinatorial Synthesis and Modification of Functional Porphyrin Libraries: Identification of New, Amphipathic Motifs for Biomolecule Binding

et al. 1999

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In the past few years there has been an explosive growth in the development of chemically diverse libraries of molecules. Combinatorial libraries have proven to be a powerful method to examine structure-function relationships, and the synthesis and screening of small molecule libraries is emerging as an important strategy for drug discovery. 1 Several strategies have been employed to create and characterize these linear-and core-structured combinatorial libraries including: (i) solid phase and solution phase synthesis and (ii) grid, deconvolution, and tagging methods to identify compounds. 1 We describe herein the synthesis and characterization of directed combinatorial libraries of mesotetraphenylporphyrin (H 2 TPP) derivatives 3 -core-structured libraries-where the largest contains 1540 compounds (including isomers) (Figure 1). The derivitization of entire libraries to make them amphipathic (Figure 1) and the iterative selection of winning compounds by DNA binding are described. As a demonstration of the methodology, we find the dipositively charged porphyrins bearing at least one hydroxyl group to be the most efficacious in the photoinitiated cleavage of plasmid DNA.Both naturally occurring and synthetic porphyrins have long been known to exist in a large variety of isomers. For example, there are 60 possible isomers for protoporphyrin due to the four methyl, two vinyl, and two propionate groups on the eight pyrrole positions, and there are 420 possible isomers of the heme a prosthetic group in cytochrome a. 4 Similarly, we and others have exploited the six possible compounds and isomers when two different arylaldehydes are employed in the synthesis of meso-substituted porphyrins [5][6][7] and libraries of chemically inert, lipophilic, alkyl-substituted H 2 TPPs have been made. 8,9 The Photo *

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Combinatorial Synthesis and Modification of Functional Porphyrin Libraries: Identification of New, Amphipathic Motifs for Biomolecule Binding

et al. 1999

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“…The synthesis of the unsymmetrical porphyrin 1 (Scheme 1), was accomplished following the procedure described by Lindsey and co-workers [21] via acid-catalyzed condensation of pyrrole with two aromatic aldehydes (4-chlorobenzaldehyde and o-vainillin). After the first step, the porphyrinogen intermediate was formed and then oxidized to porphyrin 1 with 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).…”

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Synthesis and Photodynamic Activity of 5,10,15-Tris(p-chlorophenyl)-20-(2- hydroxy-3-methoxyphenyl)-21H,23H-porphyrin

2017

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Photodynamic therapy (PDT) is an effective option for the treatment of solid neoplastic tumors, as well as non-malignant diseases such as dermatological, ophthalmological and benign pathologies. PDT destroys cancer cells by photochemical generation of reactive oxygen species upon absorption of visible light by a photosensitizing agent (PS). Here, we describe the synthesis and characterization of the unsymmetrical A3B porphyrin 5,10,15-Tris(p-chlorophenyl)-20-(2-hydroxy-3-methoxyphenyl)-21H,23H-porphyrin, which presents different groups at the meso positions, p-chlorophenyl and 2-hydroxy-3-methoxyphenyl and is a novel target molecule in order to evaluate the synergistic effect of these hydrophobic and hydrophilic moieties distributed unsymmetrically on the porphyrin macrocycle. We demonstrated the in vitro cytotoxic effect of the synthesized porphyrin, by the WST-1 assay on a cultured human cervical adenocarcinoma cell line (HeLa ATCC: CCL-2), as well as the presence of apoptosis by T.U.N.E.L. assay. We compared the phototoxicity and intrinsic cytotoxicity of the PS and found a considerable difference in the IC50 between phototoxic activity (1.5 μM) and intrinsic cytotoxicity (7 μM). The results of the induction of apoptosis on HeLa cells treated with the unsymmetrical porphyrin at a final concentration of 80 μM showed 15% apoptotic cells, whereas the untreated HeLa cells had only 2.5% apoptotic cells.

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ChemInform Abstract: Synthesis of Tetraphenylporphyrins Under very Mild Conditions.

Abstract: Pyrrole (I) and the aromatic aldehydes (II) are combined to form the intermediates (III).

Cited by 2 publications

References 1 publication

Combinatorial Synthesis and Modification of Functional Porphyrin Libraries: Identification of New, Amphipathic Motifs for Biomolecule Binding

Combinatorial Synthesis and Modification of Functional Porphyrin Libraries: Identification of New, Amphipathic Motifs for Biomolecule Binding

Synthesis and Photodynamic Activity of 5,10,15-Tris(p-chlorophenyl)-20-(2- hydroxy-3-methoxyphenyl)-21H,23H-porphyrin

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