Novel hydrophilic galactose-conjugated chlorin e6 derivatives for photodynamic therapy and fluorescence imaging

Carbohydrate–macrocycle conjugates for biomedical applications

“…26 Conjugation at C-6 of galactose is another option to release the hydroxyl group at C-1 as a hydrogen bond acceptor to bind galactin-1. [27][28][29][30][31][32] 2.1.1. CuAAC reaction.…”

1H NMR Quantitative Determination of Chlorophyll a in the Spirulina Biomass

“…В качестве объекта исследования выбрана воздушносухая биомасса спирулины (производство «Frontier co-op», Норвегия), использованная нами ранее в качестве сырья для получения феофитина а (1) [35] и метилфеофорбида а (2). [6,[45][46][47][48][49][50][51] Спектры ЯМР 1 Н записывали на спектрометре «Bruker Avance II 300» (300. Определение массовой доли хлорофилла а в биомассе спирулины.…”

Novel Hydrophilic Conjugates of Chlorin e6 with Fructose: Synthesis and Estimation of Photodynamic Activity

“…[2] For the introduction of carbohydrate fragments to the periphery of the chlorophyll a derivatives macrocycle, click chemistry, [2,13] metathesis reactions, [2] the formation of ester [23,24] and amide bonds, [2] as well as alkylation of amino groups. [25] In the case of alkylation of amino groups, a stable C-N-C bond is formed between the fragments of chlorin e 6 and galactose. [25] Insertion of fructose moieties may promote active transport because fructose is selectively taken up by cells via the carbohydrate transporter GLUT5 and GLUT5 is abundantly expressed in many cancers.…”

“…[25] In the case of alkylation of amino groups, a stable C-N-C bond is formed between the fragments of chlorin e 6 and galactose. [25] Insertion of fructose moieties may promote active transport because fructose is selectively taken up by cells via the carbohydrate transporter GLUT5 and GLUT5 is abundantly expressed in many cancers. [26] In the present work, chlorin e 6 derivatives with one and two fructose fragments on the periphery of the macrocycle were synthesized by alkylation of the amino groups of chlorin e 6 derivatives with diisopropylidene fructose triflate followed by removing isopropylidene protection in acidic conditions (Scheme), and the photodynamic activity of the compounds obtained was evaluated using cultures of cancer cells of the HeLa (cervical cancer cells), А549 (lung adenocarcinoma) and HT-29 (human colon adenocarcinoma) lines as a test object.…”