The First Selenoanhydride in the Series of Chlorophyll a Derivatives, Its Stability and Photoinduced Cytotoxicity

Abstract

In this work, we obtained the first selenium-containing chlorin with a chalcogen atom in exlocycle E. It was shown that the spectral properties were preserved in the target compound and the stability increased at two different pH values, in comparison with the starting purpurin-18. The derivatives have sufficiently high fluorescence and singlet oxygen quantum yields. The photoinduced cytotoxicity of sulfur- and selenium-anhydrides of chlorin p6 studied for the first time in vitro on the S37 cell line was found to be two times higher that of purpurin-18 and purpurinimide studied previously. Moreover, the dark cytotoxicity increased four-fold in comparison with the latter compounds. Apparently, the increase in the dark cytotoxicity is due to the interaction of the pigments studied with sulfur- and selenium-containing endogenous intracellular compounds. Intracellular distributions of thioanhydride and selenoanhydride chlorin p6 in S37 cells were shown in cytoplasm by diffusion distribution. The intracellular concentration of the sulfur derivative turned out to be higher and, as a consequence, its photoinduced cytotoxicity was higher as well.

Thiocarbonyl Derivatives of Natural Chlorins: Synthesis Using Lawesson’s Reagent and a Study of Their Properties

“…Previously, our team developed synthetic approaches to cyclic chlorin p 6 thioanhydride ( 2 ), which was found to be a promising photosensitizer [ 32 , 33 ]. Because the method for the synthesis of thioanhydrides from phthalic and 1,8-naphthalic anhydrides and their derivatives [ 34 , 35 , 36 ] using thionating Lawesson’s reagent is known in the literature, in this work, we performed a similar reaction with purpurin-18 ( 1 ) under basic conditions ( Scheme 1 ).…”

“…UV-Vis (4% micellar solutions Kolliphor ELP) λ max , nm (relative intensities of peaks): 406 (33,858), 508 (10,500), 675 (12,703)…”

Development of a Dosage form for a Photoswitchable Local Anesthetic Ethercaine

“…Both substances are surfactants capable of forming direct micelles in aqueous solutions for loading hydrophobic compounds that are sparingly soluble in water. We chose a 4% concentration of Kolliphor ELP as the initial concentration that is suitable for the solubilization of hydrophobic dyes but is safe for clinical use, including for intravenous administration [30][31][32]. In the case of other administration routes, for example, for ophthalmic use, this concentration can be increased [33].…”

Biomimetic Materials Based on Poly-3-Hydroxybutyrate and Chlorophyll Derivatives

“…It possesses antioxidant, antigenotoxic and antimutagenic properties [7][8][9]. Its derivatives are bioactive, easily modified and their synthesis cost is low [5,10,11]. Industrial forms of chlorophyll are well known, and they are successfully used in food industry, in cosmetics and medicine [9,12].…”