Synthesis of glycosylated cationic porphyrins as potential agents in photodynamic therapy

Driaf, K.; Granet, Robert; Krausz, Pierre; Kaouadji, Mourad; Verneuil, Bernard; Thomasson, F.; Chulia, Albert J.; Spiro, M.; Biais, Jean-Claude; Bolbach, G.

doi:10.1139/v96-172

Cited by 45 publications

(21 citation statements)

References 15 publications

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“…[1][2][3] More recently, porphyrins have attracted even more attention from researchers in various fields due to their phototherapeutic properties. [4][5][6] Photodynamic therapy (PDT) is a form of neoplastic diseases treatment using a photosensitizer, oxygen and light. The exogenous photosensitizer localises in tumours with a high degree of selectivity after its administration.…”

Section: Introductionmentioning

confidence: 99%

A novel chlorin derivative of Meso-tris(pentafluorophenyl)-4-pyridylporphyrin: synthesis, photophysics and photochemical properties

Maestrin¹,

Ribeiro²,

Tedesco³

et al. 2004

J. Braz. Chem. Soc.

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A terapia fotodinâmica (TFD) está baseada na administração e no acúmulo de fotossensibilizador, por exemplo, de tipo porfirina ou clorina, em tecidos doentes. As clorinas apresentam propriedades fotofísicas semelhantes àquelas das porfirinas, mas com intensificação e deslocamento das bandas Q, o que faz com que sejam bons candidatos para TFD. Neste trabalho relata-se a síntese da 5,10,15-tris(pentafluorofenil)-20-(4-piridil)porfirina, (2), e das clorinas isômeras 4, (5,10,20-tris(pentafluorofenil)-15-(4-piridil)-tetra-hidro-1H-N-metil-pirrolo[3,4-b]porfirina e 5, (5,10,15-tris(pentafluorofenil)-20-(4-piridil)-tetra-hidro-1H-N-metil-pirrolo[3,4-b]porfirina, obtidas a partir de 2, por reação de cicloadição 1,3-dipolar com um ileto azometínico, e respectivas caracterizações estruturais por UV-Vis, RMN e EM-FAB. Foram avaliadas as propriedades fotofísicas, fotoquímicas e fotodegradativas para a nova clorina 4, obtida com melhor rendimento que o seu isômero 5. O rendimento quântico de fotodegradação (φ Fd , mol Einstein -1 ) foi de 0,047±0,014. Foram ainda realizados testes com ácido úrico para demonstrar a capacidade do fotossensibilizador na produção de 1 O 2 . Os resultados mostraram que a nova clorina 4 pode ser considerada como um bom fotossensibilizador para TFD.Photodynamic therapy (PDT) is based on the accumulation of a photosensitizer, such as a porphyrin or a chlorin, in a malignant tissue after its administration. Chlorins exhibit photophysical properties similar to those of the porphyrin macrocycles, but with intensified and red-shifted Q bands, making chlorin-containing systems even better candidates for PDT. In this contribution, we report the synthesis of 5,10,15-tris(pentafluorophenyl)-20-(4-pyridyl)porphyrin, (2) and its transformation to the novel chlorin derivatives 4, (5,10,20-tris(pentafluorophenyl)-15-(4-pyridyl)-tetrahydro-1H-N-methyl-pyrrolo [3,4-b]porphyrin and 5, (5,10,15-tris(pentafluorophenyl)-20-(4-pyridyl)-tetrahydro-1H-N-methyl-pyrrolo[3,4-b]porphyrin) by 1,3-dipolar cycloaddition with an azomethine ylide. The new products have been characterized by UV-Vis, 1 H NMR and FAB-MS. The photophysics, photochemical and photobleaching properties of chlorin 4 have been evaluated. Its quantum yield of photobleaching (φ Pb , mol Einstein -1 ) was 0.047±0.014. In order to demonstrate the production of 1 O 2 when 4 is used as a photosensitizer, uric acid tests have been carried out. The results indicate that chlorin 4 can be considered a promising photosensitizer in PDT.

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Section: Introductionmentioning

confidence: 99%

A novel chlorin derivative of Meso-tris(pentafluorophenyl)-4-pyridylporphyrin: synthesis, photophysics and photochemical properties

Maestrin¹,

Ribeiro²,

Tedesco³

et al. 2004

J. Braz. Chem. Soc.

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“…[215] Note: all are Beta isomers (apart from mannose which is alpha) unless stated as alpha (or beta for mannose) or a mixture of the two. pyridiniumyl)}porphyrin [190] . The respective A 3 B neutral precursor porphyrins with one glycoside residue (glucoside, maltoside and lactoside) (131, 139, 147, 148, 151, 152) were synthesized via the Little method [191] by condensation of pyrrole, 4-pyridinecarboxaldehyde, and ortho-or para-peracetylated glycosyloxybenzaldehyde derivatives in 6-7 % yield.…”

Section: Unsymmetrically Substituted Glycoporphyrinsmentioning

confidence: 99%

“…The first series of monosubstituted tristolyl glycoporphyrins were prepared starting from the mono-hydroxyphenyl-tolyl porphyrins 406o,p obtained with propionic acid via the Little method followed by substitutions with 3-bromo-propan-1-ol and glycosylation with four protected mono-and disaccharides affording 408-411 in 20-70 % yield (Scheme 12) [226] . The second series, unsymmetrical pyridyl mono-glycosylated porphyrins (131, 139, 147, 148, 151, 152) substituted with protected mono-and disaccharides, were synthesized according to the Adler-Long method via glycosylated benzaldehydes in ~ 6 % yield [189,190] . For a comparative study the symmetric tetraglucosyl derivative 29 was also synthesized [225] .…”

Section: Glycosidation Reactions O-linked Systemsmentioning

confidence: 99%

“…Similarly, four series of meso-tetraaryl-glycoporphyrins were synthesized with protected and de-protected hydroxyl groups to evaluate their photo-inactivation of HSV-1 and HSV-2 herpes simplex virus [30] . Three different classes of porphyrins (83,190,197) were prepared by Rothemund or cross-Rothemund reactions and porphyrin 190 was reacted with hexafluorobenzene affording 198 in addition to the series. The first two series of glycoporphyrins were synthesized via the coupling of tetraphenylporphyrins with a hydroxyl group (190) [30] .…”

Section: Glycosidation Reactions O-linked Systemsmentioning

confidence: 99%

“…Three different classes of porphyrins (83,190,197) were prepared by Rothemund or cross-Rothemund reactions and porphyrin 190 was reacted with hexafluorobenzene affording 198 in addition to the series. The first two series of glycoporphyrins were synthesized via the coupling of tetraphenylporphyrins with a hydroxyl group (190) [30] . All porphyrin derivatives were tested against HSV-1 and HSV-2 in Vero cells.…”

Section: Glycosidation Reactions O-linked Systemsmentioning

confidence: 99%

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Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Moylan¹,

Scanlan²,

Senge

2015

CMC

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Abstract:This review presents an in-depth overview of the modification of porphyrins with bioconjugates and their applications in medicine today. Porphyrin bioconjugates ranging from nucleotides to steroids are under active scrutiny. However, carbohydrates have been at the forefront of such research in recent years and offer significant potential. This is attributed to their own selectivity to lectins on the surface of cancer cells and their influence on the amphiphilicity of the porphyrin macrocycle. These characteristics and the tendency of porphyrin photosensitizers to accumulate in tumor tissues make glycoporphyrins promising candidates for use as photosensitizers. Thus, a detailed overview of the synthesis and biological evaluation of glycoporphyrins is given with a particular focus on their applications in photodynamic therapy and their future prospects as drug candidates have been reported.

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Synthesis of meso-nitrophenylporphyrins covalently linked to a polyphenylene chain bearing methoxy groups

Durantini

2000

J. Porphyrins Phthalocyanines

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A convenient procedure for the synthesis of polyphenylene porphyrin dyads is described. The dyads consist of a meso-nitrophenylporphyrin covalently linked to a polyphenylene chain by an amide bond. The final phenyl group in the chain bears electron donor methoxy groups. The π-conjugated chain was obtained in excellent yield via a Wittig–Horner reaction, which produces a new double bond (E isomer) incorporating either — COOCH 3 or E isomer) incorporating either — CON ( OCH 3)( CH 3) functional groups. Expansion of the conjugated chain involves the reduction of these groups to aldehydes followed by a second Wittig–Horner reaction. 5-(4-Aminophenyl)-10,15,20-tris(4-nitrophenyl)porphyrin was synthesized from meso-(4-nitrophenyl)dipyrromethane. The E isomer) incorporating either — NO 2 groups in para positions of the peripheral phenyl rings give extra electron-withdrawing character to the porphyrin macrocycles. Coupling of the polyphenylene acids with aminoporphyrin results in the desired dyads. These dyads have moieties with different electron donor–acceptor properties. This present strategy may be easily used for preparation of other similar dyad derivatives. These compounds can be suitable for photodynamic therapy.

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Synthesis of glycosylated cationic porphyrins as potential agents in photodynamic therapy

Cited by 45 publications

References 15 publications

A novel chlorin derivative of Meso-tris(pentafluorophenyl)-4-pyridylporphyrin: synthesis, photophysics and photochemical properties

A novel chlorin derivative of Meso-tris(pentafluorophenyl)-4-pyridylporphyrin: synthesis, photophysics and photochemical properties

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Synthesis of meso-nitrophenylporphyrins covalently linked to a polyphenylene chain bearing methoxy groups

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