Details

Autor(en) / Beteiligte

• Jinadasa, R. G. Waruna
• Zhou, Zehua
• Vicente, M. Graça H
• Smith, Kevin M

Titel

Syntheses and cellular investigations of di-aspartate and aspartate-lysine chlorin e6 conjugatesElectronic supplementary information (ESI) available: Copies of 1H NMR spectra, 13C NMR spectra, dark toxicity curves, and subcellular localizations for chlorin e6 (21 pages). See DOI: 10.1039/c5ob02241j

Erscheinungsjahr

2016-01

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Chlorin e 6 is a tricarboxylic acid degradation product of chlorophyll a . Four chlorin e 6 bis(amino acid) conjugates were regioselectively synthesized bearing two aspartate conjugates in the 13 1 ,17 3 - and 15 2 ,17 3 -positions, or at the 13 1 ,15 2 via an ethylene diamine linker. One additional conjugate bearing two different amino acids, lysine at 13 1 via an ethylene diamine linker and an aspartate at 15 2 via a β-alanine linker was also synthesized. The cytotoxicity and uptake of four di(amino acid) chlorin e 6 conjugates were investigated in human HEp2 cells, and compared with chlorin e 6 . The most cytotoxic and most taken up conjugates were the zwitterionic 13 1 ,15 2 -disubstituted conjugates 28 and 33 ; these also localized in multiple organelles. In contrast, the anionic 13 1 ,17 3 - and 15 2 ,17 3 -di-aspartyl chlorin e 6 conjugates 12 and 13 showed low dark cytoxicity and lower phototoxicity compared with chlorin e 6 . Regioselective syntheses of chlorin e 6 bis(amino acid) conjugates bearing aspartates in the 13 1 ,17 3 -, 15 2 ,17 3 - and 13 1 ,15 2 -positions, and their cell studies are reported.