Photodynamic therapy is a binary treatment now accepted in clinic for various malignancies in several countries around the world. Phthalocyanine molecules are second-generation photosensitizers with enhanced photophysical and photochemical properties over those of porphyrins. They have been shown to be phototoxic against a number of cell types and tumor models. A great deal of research has been devoted to the elucidation of their mechanism of action and mode of cell death. The present paper reviews phthalocyanine pre-clinical anti-cancer research with emphasis on phthalocyanine induced apoptosis using a silicon phthalocyanine, Pc4. A brief summary of the latest clinical results using phthalocyanines is presented.

Current status of phthalocyanines in the photodynamic therapy of cancer

Synthetic pathways to water-soluble phthalocyanines and close analogs

Phthalocyanines and porphyrins are versatile functional pigments with a wide range of applications. These macrocyclic compounds contain four isoindole or pyrrole nitrogen atoms, which can complex with a range of metal ions. Large rare earth metal ions can bring together these tetrapyrrole derivatives to form sandwich-type double- and triple-decker complexes. Depending on the metal centers and the nature of the macrocyclic ligands, these compounds exhibit tunable spectroscopic, electronic, and redox properties, and different extents of intramolecular π−π interactions. Some of the properties of the sandwich-type complexes are unique and enable them to be used as advanced materials for various applications. Over the last two decades, a vast number of homoleptic and heteroleptic double- and triple-decker complexes have been synthesized. With improvements in synthetic procedures, researchers have prepared novel sandwich complexes that could not have been prepared by traditional methods. This Account highlights...

A decade journey in the chemistry of sandwich-type tetrapyrrolato-rare Earth complexes.

The present invention relates to a series of novel phthalocyanine compositions (or compounds) suitable for use as photosensitizers for photodynamic therapy. Specifically, the invention relates to a series of new aluminum (Al) and/or silicon (Si) phthalocyanines having substituted amine or quaternary ammonium axial ligands attached to the central metal, and the use of these new phthalocyanine compositions for the treatment of cancer through photosensitization. Moreover, the present invention is directed to the methods of preparing these compositions for use in photodynamic therapy.

Phthalocyanine photosensitizers for photodynamic therapy

Aus Halogenboranen und Organohalogenboranen (RBX
2∶R=C6H5, Cl, Br;X=F, Cl, Br) sowie aus Organoboranen oder Thioboranen entstehen mit Phthalodinitril Triisoindolo-[1,2,3-cd∶1′,2′,3′-gh∶1″,2″,3″-kl][2,3a,5,6a,8,9a,9b]-hexaazaboraphenalene von denen die B−Cl- und B−F-Verbindungen naher charakterisiert werden. Dekaboran(14), Diboran(6) oder Boranaddukte von Stickstoffbasen liefern hingegen mit Phthalodinitril metallfreies Phthalocyanin.

P. A. Barrett

Papers

382. Phthalocyanines. Part VII. Phthalocyanine as a co-ordinating group. A general investigation of the metallic derivatives

372. Phthalocyanines and related compounds. Part XVI. The halogenation of phthalocyanines