Pub No:
341
Title:
Porphyrin-based Photosensitizers for use in Photodynamic Therapy
Authors:
Sternberg, E., Bruckner, C., and David Dolphin
Journal:
Tetrahedron Reports
Year:
1998
Pages:
54, 4151-4202
Abstract:
This review gives an introduction to the photophysical, chemical and medicinal basis of Photodynamic Therapy (PDT) and reviews the synthesis and properties of a wide variety of porphyrin-based photosensitizers, including porphyrins, chlorins and bacteriochlorins, which have been used or suggested as photosensitizers in PDT. polypyrrolic macrocycles known as expanded porphyrins or the phthalocyanines, have not been included. Photodynamic therapy is a medical treatment which employs the combination of light and a drug to bring about a cytotoxic or modifying effect to cancerous or otherwise unwanted tissue. It derives great promise from its dual-selective mode of action: A drug (photosensitizer) of negligible dark toxicity is introduced into the body and accumulates preferentially in rapidly dividing cells. When the drug reaches an appropriate ratio of accumulation in diseased versus healthy tissue, a carefully regulated light dose is shone onto the diseased tissue. Light activates the drug and elicits the toxic action. The amount of light needs to be large enough to cause the desired response in the tissue, but small enough to spare the surrounding (and incidentally illuminated) healthy tissue from extensive damage. Shortly after treatment, the damaged cells become necrotic, or suitably modified. The review contains 252 references and covers the following topics 1. General Introduction to Photodynamic Therapy 1.1 Photodynamic therapy 1.2 Historyof PDT 1.3 The history of the first generation PDT agent hematoporphyrin derivative 1.4 Photophysical basis of photodynamic therapy 1.5 Phototoxicity as it relates to therapy 1.6 Potential fields of appIication for PDT 1.7 The delivery of light 1.8 The profile of an ideal PDT drug 2. General Aspects of Porphyrin Photosensitizers 2.1 Availability of porphyrinic materials 2.2 The optical spectra of porphyrins and chlorins 2.3 The synthesis of chlorins 3. Pro-Drugs as Sources of Porphyrins forPDT 4. Derivatives of Hematoporphyrin and Protoporphyrin 4.1 Side chain modifications 4.2 Electrocyclic reactions involving hemato- and protoporphyrins 4.3 Meso-Position manipulation 5. Modification of synthetic β-alkylporphyrins 5.1 β-Hydroxy- and β-oxochlorins 5.2 Porphyrins and chlorins with exocyclic rings and synthetically related systems 6. Modifications of meso-Tetraphenylporphyrins 7. Miscellaneous Synthetic Porphyrinic Compounds 7.1 Porphyrins with extended chromophores 7.2 Distortedporphyrins 7.3 Secochlorins 7.4 Porphyrins incorporating a six-membered ring 8. Naturally Occurring Chlorins and Bacteriochlorins 8.1 Chlorins 8.2 BacteriochIorins 9. Porphyrins Conjugated to Biomolecules 9.1 Antibody conjugates 9.2 Steroidconjugates 9.3 Sugarconjugates 9.4 Mono-and polynucleotide conjugates 10. Porphyrin Isomers 10.1 Porphycene and related pigments 10.2 N-Confused and carbaporphyrins

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