Fluorinated porphyrinoids and their biomedical applications
Porphyrins, phthalocyanines, chlorins and corroles create a compact group of macrocyclic compounds of established utility in medicine and technology. Fluorine atom insertion to their structures belongs to one of many ongoing approaches for improving their potency. The presence of fluorine in the structure of a photosensitizer may enrich it with required pharmacokinetic features. Photostability, high level of singlet oxygen production, lipophilicity and selective accumulation in tumor cells have made the fluorinated porphyrinoids potential entities for photodynamic therapy. Moreover, photosensitizers possessing intrinsic fluorescence may be applied as agents in photodynamic diagnosis of cancer. Noteworthy, magnetic resonance of fluorinated compounds constitutes excellent probe for sensitive and minimally invasive imaging.Porphyrins constitute the largest group within fluorinated porphyrinoids of potential anticancer and antimicrobial properties. Skillful combination of fluorine substituents with other functional groups in their structures, including glycol or sugars led to novel molecules possessing outstanding phototoxicity in both in vitro and in vivo studies. Furthermore, fluorinated porphyrins were researched as biomimetic systems imitating the active sites of some enzymes. Fluorinated chlorins are considered as promising photosensitizers due to a strong absorption and the least harmful effects to human tissues. Fluorine containing groups introduced to the periphery of phthalocyanines improved their solubility in common solvents and thus enhanced applications in in vitro and in vivo researches. Lately investigated porphyrinoids belonging to corroles showed on one hand potential as photosensitizers, but on the other hand they were found as catalytic anti-oxidants for attenuation of diabetes mellitus.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Fluorine atom insertion into the porphyrinoid structure may improve its potency in medicine. ► Fluorinated porphyrinoids possess high level of singlet oxygen production. ► Fluorinated porphyrinoids accumulate in tumor cells showing potential for photodynamic therapy. ► Magnetic resonance of fluorinated compounds constitutes probe for minimally invasive imaging.
Journal: Journal of Photochemistry and Photobiology C: Photochemistry Reviews - Volume 12, Issue 4, December 2011, Pages 304–321