Dual Role of Subphthalocyanine Dyes for Optical Imaging and Therapy of Cancer

Abstract

The family of subphthalocyanine (SubPc) macrocycles represents an interesting class of nonplanar aromatic dyes with promising features for energy conversion and optoelectronics. The use of SubPcs in biomedical research is, on the contrary, clearly underexplored, despite their documented high fluorescence and singlet oxygen quantum yields. Herein, for the first time it is shown that the interaction of these chromophores with light can also be useful for theranostic applications, which in the case of SubPcs comprise optical imaging and photodynamic therapy (PDT). In particular, the article evaluates, through a complete in vitro study, the dual-role capacity of a novel series of SubPcs as fluorescent probes and PDT agents, where the macrocycle axial substitution determines their biological activity. The 2D and 3D imaging of various cancer cell lines (i.e., HeLa, SCC-13, and A431) has revealed, for example, different subcellular localization of the studied photosensitizers (PS), depending on the axial substituent they bear. These results also show excellent photocytotoxicities, which are affected by the PS localization. With the best dual-role PS, preliminary in vivo studies have demonstrated their therapeutic potential. Overall, the present paper sets the bases for an unprecedented biomedical use of these well-known optoelectronic materials.

Alkane Chain‐extended Pterin Through a Pendent Carboxylic Acid Acts as Triple Functioning Fluorophore, 1O2 Sensitizer and Membrane Binder

“…Over the past 6–8 years, “smart” compounds that possess dual fluorescence sensing and singlet oxygen sensitizing properties have become a hot topic , with success reported in dual function image‐guided and photodynamic therapy applications (PDT) . Indeed, our previous O ‐ and N ‐decyl‐pterins possessed good singlet oxygen quantum yields (Φ ∆ ), but had poor fluorescence quantum yields (Φ F ) some 4–30 fold less compared to native pterin, thereby fulfilling only two of three facets, even though a minor fluorescence increase was observed when intercalated in the membrane .…”

Novel axial substituted subphthalocyanine sensitized titanium dioxide H12SubPcB‐OPh2OH/TiO2 photocatalyst: Synthesis, density functional theory calculation, and photocatalytic properties

“…[48,49] In addition, it's intense absorption (550-600 nm) and emission in the visible region owing to its 14-π electron configuration system have attracted widespread attention in the light-harvesting field. [50][51][52][53][54] Numerous studies have demonstrated the potential of SubPcs as functional materials in a variety of applications such as photodynamic therapy (PDT), [55,56] organic field-effect transistors (OFETs), [57] organic light-emitting diodes (OLEDs), [58] and organic photovoltaic cells (OPVs) [59] in the last years. However, the fabrication of SubPcs sensitized semiconductor materials and their properties under visible-light irradiation have rarely been studied.…”

Pyrene/coumarine-subphthalocyanine conjugates as light harvesting systems with intramolecular energy transfer

“…They are conic-shaped macrocycles, with a 14-π electron aromatic core. This scaffold is used in many fields, such as organic material [7], photodynamic therapy [8] or optoelectronic [9,10]. Most functionalizations of the SubPc moieties are done by substitution of the axial halogen.…”