Carbohydrate-Porphyrin Conjugates with Two-Photon Absorption Properties as Potential Photosensitizing Agents for Photodynamic Therapy

被引：57

作者：

Achelle, Sylvain ^{[1
,2
]}

Couleaud, Pierre ^{[3
]}

Baldeck, Patrice ^{[4
]}

Teulade-Fichou, Marie-Paule ^{[1
,2
]}

Maillard, Philippe ^{[1
,2
]}

机构：

[1] Univ Paris Sud, CNRS, Inst Curie, UMR 176, F-91405 Orsay, France

[2] Univ Paris Sud, Inst Curie, Sect Rech, Ctr Univ, F-91405 Orsay, France

[3] Nancy Univ, Lab React & Genie Procedes, UPR 3349, F-54001 Nancy, France

[4] Univ Grenoble 1, Spectrometrie Phys Lab, CNRS, UMR 5588, F-38402 St Martin Dheres, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 07期

关键词：

Porphyrinoids; Photodynamic therapy; Two-photon absorption; Carbohydrates; Conjugation; GLYCOCONJUGATED PORPHYRINS; RESONANCE ENHANCEMENT; HUMAN RETINOBLASTOMA; TRIPLE BONDS; DIMERS; TUMOR; PDT; EFFICIENCY; STRATEGIES; MEMBRANE;

D O I：

10.1002/ejoc.201001209

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report the synthesis of a series of conjugated zinc porphyrin oligomers designed as photodynamic therapy agents. These compounds exhibit exceptionally high two-photon absorption cross-sections, redshifted linear absorption spectra, and high singlet oxygen quantum yields, making them ideal for one-photon- and two-photon-excited photodynamic therapy. These products are substituted by three alpha-mannose units on each chromophore with the aim to target tumor cells with over-expressing lectin-type membrane receptors.

引用

页码：1271 / 1279

页数：9

共 66 条

[1] Building molecular wires from the colours of life: conjugated porphyrin oligomers [J].

Anderson, HL .

CHEMICAL COMMUNICATIONS, 1999, (23) :2323-2330

[2]

[Anonymous], 1998, ANGEW CHEM

[3] DIMERIC PORPHYRINS LINKED BY CONJUGATED GROUPS CONTAINING TRIPLE BONDS - THE CRYSTAL-STRUCTURE OF THE NICKEL OCTAETHYLPORPHYRIN DIMER BRIDGED BY 2,5-DIETHYNYLTHIOPHENE [J].

ARNOLD, DP ;

JAMES, DA ;

KENNARD, CHL ;

SMITH, G .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (18) :2131-2132

[4] Butadiyne-linked bis(chlorin) and chlorin-porphyrin dyads and an improved synthesis of bis[octaethylporphyrinatonickel(II)-5-yl]butadiyne using the Takai iodoalkenation [J].

Arnold, DP ;

Hartnell, RD .

TETRAHEDRON, 2001, 57 (07) :1335-1345

[5] SOME REACTIONS OF MESO-FORMYLOCTAETHYLPORPHYRIN [J].

ARNOLD, DP ;

JOHNSON, AW ;

MAHENDRAN, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (04) :366-370

[6] THE PREPARATION OF NOVEL PORPHYRINS AND BIS(PORPHYRINS) USING PALLADIUM CATALYZED COUPLING REACTIONS [J].

ARNOLD, DP ;

NITSCHINSK, LJ .

TETRAHEDRON LETTERS, 1993, 34 (04) :693-696

[7] Dimers and model monomers of nickel(II) octaethylporphyrin substituted by conjugated groups comprising combinations of triple bonds with double bonds and arenes .1. Synthesis and electronic spectra [J].

Arnold, DP ;

James, DA .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (11) :3460-3469

[8] Lead structures for applications in photodynamic therapy. Part 2: Synthetic studies for photo-triggered release systems of bioconjugate porphyrin photosensitizers [J].

Bakar, Mohd Bakri ;

Oelgemoeller, Michael ;

Senge, Mathias O. .

TETRAHEDRON, 2009, 65 (34) :7064-7078

[9] Synthesis of hydrophilic conjugated porphyrin dimers for one-photon and two-photon photodynamic therapy at NIR wavelengths [J].

Balaz, Milan ;

Collins, Hazel A. ;

Dahlstedt, Emma ;

Anderson, Harry L. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (05) :874-888

[10]

Ballut S, 2009, CHEM COMMUN, P224, DOI 10.1039/b816128c

← 1 2 3 4 5 6 7 →