Photodynamic therapy with decacationic [60]fullerene monoadducts: Effect of a light absorbing electron-donor antenna and micellar formulation

Abstract

We report the synthesis and anticancer photodynamic properties of two new decacationic fullerene (LC14) and red light-harvesting antenna-fullerene conjugated monoadduct (LC15) derivatives. The antenna of LC15 was attached covalently to C60> with distance of only <3.0 Ǻ to facilitate ultrafast intramolecular photoinduced-electron-transfer (for type-I photochemistry) and photon absorption at longer wavelengths. Because LC15 was hydrophobic we compared formulation in CremophorEL micelles with direct dilution from dimethylacetamide. LC14 produced more 1O2 than LC15, while LC15 produced much more HO· than LC14 as measured by specific fluorescent probes. When delivered by DMA, LC14 killed more HeLa cells than LC15 when excited by UVA light, while LC15 killed more cells when excited by white light consistent with the antenna effect. However LC15 was more effective than LC14 when delivered by micelles regardless of the excitation light. Micellar delivery produced earlier apoptosis and damage to the endoplasmic reticulum as well as to lysosomes and mitochondria.

Biological activity of fullerenes - reality and prospects

“…Это актуально в случае солидных опухолей, подействовать на которые не удается при исполь-зовании коротковолнового облучения (УФ и синий свет). Поэтому для воздействия на глубокорасполо-женные ткани необходимо применять фотосенсити-заторы, поглощающие излу чение в области больших длин волн (в красной области спектра), и увеличи-вать поглощение вещества присоединением к нему светособирающей антен ны [34].…”

Strategies to optimize photosensitizers for photodynamic inactivation of bacteria

“…Such a reaction is driven by the electrolyte salts of the buffer system which facilitates the ion exchange and the iodide-dissociation. Thus a fullerene-radical is generated which in turn reacts with oxygen to produce a superoxide-radical that is the precursor molecule to the formation of hydroxyl-radicals [52][53][54].…”

Nanotechnology for photodynamic therapy: a perspective from the Laboratory of Dr. Michael R. Hamblin in the Wellman Center for Photomedicine at Massachusetts General Hospital and Harvard Medical School

“…These compounds have been tested as photosensitizers to mediate the PDT of pathogenic microorganisms [57], cancer cells [58], and to treat mouse models of infectious disease [59]. …”