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Design and Synthesis of Novel Phenothiazinium Photosensitiser Derivatives
Author(s) -
New Olivia M.,
Dolphin David
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900118
Subject(s) - chemistry , photosensitizer , peptide , combinatorial chemistry , covalent bond , phenothiazine , peptide synthesis , rational design , photodynamic therapy , cleavage (geology) , stereochemistry , photochemistry , organic chemistry , nanotechnology , biochemistry , medicine , pharmacology , materials science , geotechnical engineering , fracture (geology) , engineering
A high‐yielding approach towards N ‐(2‐aminoethyl)‐Azure B has been established and extended towards the preparation of a functionalized peptide‐dye synthetic precursor; Boc‐protected 3‐(alkylamino)phenothiazin‐5‐ium TFA. This has been utilized in a series of reactions with various amines towards nine novel 3,7‐disubstituted phenothiazin‐5‐ium derivatives. Cleavage of the Boc group in the 3,7‐disubstituted salts allowed a further seven novel dyes to be prepared and these have been utilized in a practical methodology designed for the synthesis of 13 novel phenothiazine‐peptide conjugates. These peptide‐photosensitizer vectors consist of a covalent attachment of a tethered dye to various protected amino acid moieties including the cell‐penetrating peptide (CPP) octa‐arginine and exhibit intense absorption maxima in the 623–650 nm regions of the visible spectrum. The main goal of the studies is the design of cell‐compatible photosensitisers that may be employed in photodynamic therapy.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)