Nuclear imaging potential and in vitro photodynamic activity of Boron subphthalocyanine on colon carcinoma cells

“…Upon excitation, all of the studied SubPcs showed fluorescence emission around 585 nm, varying in intensity. Fluorescence emission is important for in vitro bioimaging , and was used in this project for subcellular localization and the study of uptake into cells (see below). Fluorescence emission spectra mirrored the absorption spectra with small Stokes shifts of approximately 10 nm, which demonstrated insignificant structural changes of molecules in their excited states.…”

Section: Results and Discussionmentioning

confidence: 99%

“…Aggregation is responsible for quenching of excited states and loss of photophysical properties. , Because of their 14 π-delocalized electrons, SubPcs possess interesting spectral and photophysical properties that are being investigated for many applications such as organic photovoltaics, organic light-emitting diodes, and fluorescent dyes. ,, These versatile tunable molecules enable attachment of different substituents to both peripheral and axial positions. This advantage together with their straightforward synthesis makes them a good alternative for other intensively studied PSs such as, e.g., BODIPY dyes. , Few recent literature reports have suggested the possibility of using SubPcs in PDT to kill bacteria , or for treatment of cancer. ,− Theranostic SubPcs combining a therapeutic (photodynamic) effect with diagnostics (cell imaging) have also been described . To the best of our knowledge, only one paper determined their half-maximal effective concentration (EC 50 ), which is a valuable parameter for comparing their activity with those of other PSs.…”

Section: Introductionmentioning

confidence: 99%

Subphthalocyanines as Efficient Photosensitizers with Nanomolar Photodynamic Activity against Cancer Cells

et al. 2021

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Because cancer is the second leading cause of death globally, investigation of new photosensitizers for photodynamic therapy is highly desirable. In this work, different peripherally substituted subphthalocyanines (SubPcs) with either a benzocrown moiety (CE-) or a tyrosine methyl ester (Tyr-) as the axial ligand have been prepared. Target SubPcs showed high Φ Δ values, >0.50 in EtOH. Both CE-and Tyr-moieties increased substantially the hydrophilicity of the compounds (log P = 1.79−2.63, noctanol/PBS). Uptake to cells, subcellular localization, and monitoring of the progression of cell death over time are described. Improved spectroscopic behavior of the CE-series in cell culture medium resulted in higher photodynamic activity versus that of the Tyr-series. In particular, the peripherally triethylsulfanyl SubPc-CE exhibited extraordinarily low EC 50 values of 2.3 and 4.4 nM after light activation and high TC 50 values of 14.49 and 5.25 μM (i.e., dark toxicity without activation) on SK-MEL-28 and HeLa cells, respectively, which rank it among the best photosensitizers ever.

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“…13,14 The lower homologues of phthalocyanines (i.e., subphthalocyanines, SubPcs) and of tetrapyrazinoporphyrazines (SubTPyzPzs), have been used as fluorophores for photochromic switches, 15,16 and as photosensitizers for photodynamic therapy of cancer. [17][18][19][20][21] The great application potential of these macrocycles has been summarized in recent reviews. 22,23 To the best of our knowledge, no aza-crown containing SubPcs and only a limited number of crown containing SubPcs have been successfully prepared with a crown at the peripheral positions 24 or a benzocrown 21 at the axial position.…”

Section: Introductionmentioning

confidence: 99%