@article {2547, title = {Design and Synthesis of Novel Phenothiazinium Photosensitiser Derivatives}, journal = {European Journal of Organic Chemistry}, number = {16}, year = {2009}, note = {ISI Document Delivery No.: 452FITimes Cited: 1Cited Reference Count: 39New, Olivia M. Dolphin, David}, month = {Jun}, pages = {2675-2686}, type = {Article}, abstract = {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 623650 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. ((C) Wiley-VCH Verlag GmbH \& Co. KGaA, 69451 Weinheim, Germany, 2009)}, keywords = {AMINATION, ANALOGS, Azure B, BENZOPHENOTHIAZINE, Cell-penetrating peptide, CELLULAR DELIVERY, Dye-peptide conjugate, Electronic spectra, METHYLENE-BLUE, Phenothiazine dye, PHOTODYNAMIC THERAPY, SERIES, TRANSDUCTION, TRANSLOCATION, TRANSPORTERS, TUMORS}, isbn = {1434-193X}, url = {://000266525100010}, author = {New, O. M. and Dolphin, D.} } @article {597, title = {Drug release characteristics of lipid based benzoporphyrin derivative}, journal = {Journal of Pharmacy and Pharmaceutical Sciences}, volume = {6}, number = {1}, year = {2003}, note = {ISI Document Delivery No.: 679QJTimes Cited: 21Cited Reference Count: 17}, month = {Jan-Apr}, pages = {13-19}, type = {Article}, abstract = {PURPOSE. The purpose of this study was to examine the transfer of verteporfin (BPDMA) from its lipid based formulation to serum proteins. METHODS. As a result of BPDMA being confined to the lipid phase, it was found that fluorescence from the photosensitizer was highly concentration quenched. This phenomenon was used to demonstrate rapid transfer of lipid-based drug to various plasma components such as albumin and lipoproteins. Gel electrophoresis was used to show transfer of drug to lipoproteins. RESULTS. Loss of fluorescence quenching showed rapid transfer of the drug from its lipid based formulation to serum proteins. Gel electrophoresis showed that both the drug and phospholipid components were transferred to the lipoprotein fraction concurrently. The electrophoretic mobility of plasma lipoproteins was increased as a result of their interaction with lipid-based BPDMA. It was also shown that the lipid-based structures were readily destabilized in the presence of relatively low concentrations of plasma, and that liposomes of this lipid composition were highly unlikely to be found intact in the circulation following intravenous injection. CONCLUSIONS. Verteporfin is rapidly transferred from its lipid based formulation to serum proteins. This rapid transfer, particularly to lipoproteins, provides a mechanism for its rapid delivery to cells.}, keywords = {DENSITY LIPOPROTEINS, DESTABILIZATION, LIPOSOMES, PHOTODYNAMIC THERAPY, PLASMA-LIPOPROTEINS, PROTEIN, TUMORS}, isbn = {1482-1826}, url = {://000182933200002}, author = {Chowdhary, R. K. and Shariff, I. and Dolphin, D.} } @article {4190, title = {An effective synthetic route to EF5}, journal = {Synthetic Communications}, volume = {28}, number = {19}, year = {1998}, note = {ISI Document Delivery No.: 117KHTimes Cited: 2Cited Reference Count: 17}, pages = {3701-3709}, type = {Article}, abstract = {EF5 (a 2-nitroimidazole containing an N-(pentafluoropropyl) acetamide substituent) is a very sensitive probe for quantifying the amount of hypoxia within cells; a much improved, short step, synthetic procedure is described for EF5, whose X-ray structure is also presented.}, keywords = {ANTIBODIES, BINDING, CELLS, COMPLEXES, CRYSTAL, HYPOXIA, TUMORS}, isbn = {0039-7911}, url = {://000075780100021}, author = {Baird, I. R. and Skov, K. A. and James, Brian R. and Rettig, S. J. and Koch, C. J.} } @article {3119, title = {PORPHYRIN CHEMISTRY PERTAINING TO THE DESIGN OF ANTICANCER DRUGS .1. THE SYNTHESIS OF PORPHYRINS CONTAINING MESO-PYRIDYL AND MESO-SUBSTITUTED PHENYL FUNCTIONAL-GROUPS}, journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie}, volume = {72}, number = {9}, year = {1994}, note = {ISI Document Delivery No.: PJ994Times Cited: 37Cited Reference Count: 46}, month = {Sep}, pages = {1894-1909}, type = {Article}, abstract = {Condensation of pyrrole with a benzaldehyde and 4-pyridinecarboxaldehyde mixture yields the six possible meso-substituted phenyl or pyridyl porphyrins. Nitration of four of these has yielded 13 other porphyrins containing one to four 4-nitrophenyl moieties, and SnCl2 reduction of eight of these nitrophenylporphyrins gives the corresponding 4-aminophenyl(phenyl)- or 4-aminophenyl(phenyl)(4-pyridyl)porphyrins. Twelve of the porphyrins are new, but all 27 are fully characterized by H-1 NMR; resonances for every proton within each of the phenyl, pyridyl, and pyrrole rings are assigned. Trends in UV-VIS data are discussed, while IR and mass spectral data are noted for selected porphyrins.}, keywords = {METALLOPORPHYRINS, MODEL, NUCLEAR MAGNETIC-RESONANCE, OXYGEN, TETRAARYLPORPHYRINS, TUMORS}, isbn = {0008-4042}, url = {://A1994PJ99400002}, author = {Meng, G. Z. G. and James, Brian R. and Skov, K. A.} }