@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 = {<Go to ISI>://000266525100010},
	author = {New, O. M. and Dolphin, D.}
}
@article {2502,
	title = {Near-Infrared Absorbing Azo Dyes: Synthesis and X-ray Crystallographic and Spectral Characterization of Monoazopyrroles, Bisazopyrroles, and a Boron-Azopyrrole Complex},
	journal = {Journal of Organic Chemistry},
	volume = {74},
	number = {15},
	year = {2009},
	note = {ISI Document Delivery No.: 476XOTimes Cited: 5Cited Reference Count: 69Li, Yan Patrick, Brian O. Dolphin, David},
	month = {Aug},
	pages = {5237-5243},
	type = {Article},
	abstract = {Symmetric 2,5-bisazopyrroles 2(a-d) were synthesized by a one-step reaction of substituted phenyl diazonium salts [R{\textquoteright}(Ph)N2+Cl-] [a, R{\textquoteright}= 4-N(CH3)(2); b, R{\textquoteright} = 2OH; c, R{\textquoteright} = 2-CO2H; d, R{\textquoteright} = 4-NO2] with pyrrole under basic conditions. Asymmetric 2,5-bisazopyrroles 3(a-d) were synthesized by reacting substituted phenyl diazonium salts [R {\textquoteright}{\textquoteright}(Ph)N2+Cl-] (a, R {\textquoteright}{\textquoteright} = 4-OCH3; b, R {\textquoteright}{\textquoteright} = H; c, R {\textquoteright}{\textquoteright} = 4-Br; d, R {\textquoteright}{\textquoteright} = 4-NO2) with 2-(4-dimethylaminophenylazo)-1H-pyrrole (1a) under the same conditions. The reactions of 2a with boron trifluoride and iodomethane provided a BF2-azopyrrole complex of 1H-pyrrolo[2,1-c]-1,2,4,5-boratriazole (4) and 2,5-bisazo-1-methylpyrrole 5. X-ray crystallographic and spectral analysis of la, 2a, 2b, and 4 showed that la has three crystal forms: 1a(I), 1a(II), and 1a(III), the latter two bearing a bicyclic ring system formed via intermolecular hydrogen bonding. Complex 4 was found to be the most planar due to a rigid trans-azo configuration and has the longest N=N bond distances (1.322 and 1.300 angstrom) and wavelength of maximum absorption (754 nm). The N=N bond distances increase in the sequence of monoazopyrrole [1a(1): 1,253 angstrom], bisazopyrrole (2a: 1.283 angstrom), bisazopyrrole with intramolecular hydrogen bonding (2b: 1,293 and 1.293 angstrom), and the BF2-azopyrrole complex. Their maximum absorptions shift bathochromically in the sequence of monoazopyrrole (1a: 443 nm), bisazopyrroles [2(a-d), 3(a-d), 5: 486-615 nm), and the BF2-azopyrrole complex. These results are important for the design of near-infrared absorbing azo dyes and suggest an efficient path for the preparation of near-infrared absorbing azo dyes by effectively enhancing pi-electron delocalization.},
	keywords = {C-13 NMR, CI-DISPERSE-ORANGE-29, CRYSTAL-STRUCTURE, DERIVATIVES, DISAZO DYES, HETEROCYCLIC DIAZO COMPONENTS, INTRAMOLECULAR PROTON-TRANSFER, NONLINEARITIES, optical, PHOTODYNAMIC THERAPY, SOLID-STATE},
	isbn = {0022-3263},
	url = {<Go to ISI>://000268480300014},
	author = {Li, Y. and Patrick, B. O. and Dolphin, D.}
}
@article {2163,
	title = {Cross-metathesis of the vinyl group, on tetrapyrrolic macrocycles: Reactivity, selectivity, and mechanism},
	journal = {Journal of Organic Chemistry},
	volume = {73},
	number = {17},
	year = {2008},
	note = {ISI Document Delivery No.: 344EDTimes Cited: 3Cited Reference Count: 32Liu, Xin Sternberg, Ethan Dolphin, David},
	month = {Sep},
	pages = {6542-6550},
	type = {Article},
	abstract = {To find a general strategy for modifying the peripheral structure of vinylchlorin and porphyrin substrates, cross-metathes is on the vinyl group of these tetrapyrrolic macrocycles was investigated. The N-heterocyclic carbene-containing ruthenium complex 3 efficiently catalyzed the cross-metathes is (CM) of vinylchlorins and vinylporphyrins with a variety of olefins in high E-stereoselectivity. Different substituents on the olefin dramatically influenced the reaction. While the chlorins were more reactive than the porphyrins (as free bases), the corresponding zinc complexes showed higher activity. The reaction mechanism was investigated, and an empirical model for selective CM was applied to our studies to direct further reactions.},
	keywords = {A DERIVATIVES, CATALYSTS, chlorins, OLEFIN METATHESIS, PHOTODYNAMIC THERAPY, PHOTOSENSITIZERS, RUCL2(=CHR)(PR(3))(2)},
	isbn = {0022-3263},
	url = {<Go to ISI>://000258908000009},
	author = {Liu, X. and Sternberg, E. and Dolphin, D.}
}
@article {1230,
	title = {Separation of porphyrin-based photosensitizer isomers by laser-induced fluorescence capillary electrophoresis},
	journal = {Electrophoresis},
	volume = {26},
	number = {20},
	year = {2005},
	note = {ISI Document Delivery No.: 982VMTimes Cited: 3Cited Reference Count: 43},
	month = {Oct},
	pages = {3861-3868},
	type = {Article},
	abstract = {Methods for the separation of photosensitizer isomers, such as benzoporphyrin derivative monoacid, benzoporphyrin ethyl monoacid, 2-[1-hexyloxyethyl]-2-devinylpyropheophorbide-a, diethyleneglycol diester benzoporphyrin derivative, tin ethyl etiopurpurin, and phthalocyanine tetrasulfonate, have been systematically developed by CE. Detection was accomplished by UV absorption at 214 nm or by LIF with excitation at 442/488 nm and emission at 690 nm. The effects of three major experimental parameters of buffer types, organic solvents, and surfactant additives are described. The optimized separation conditions were determined so as to provide satisfactory separation efficiency and analysis time. The methods are shown to be suitable for the separation and determination of porphyrin and phthalocyanines regioisomers, diastereoisomers, and enantiomers.},
	keywords = {chiral additives, CHLORIN, DERIVATIVES, EFFICACY, ENANTIOMERS, FLUORESCENCE DETECTION, FRACTION, LIGHT, PANCREATIC-CANCER CELLS, PERFORMANCE LIQUID-CHROMATOGRAPHY, pharmacokinetics, PHOTODYNAMIC THERAPY, PHTHALOCYANINES, porphyrins, regioisomers},
	isbn = {0173-0835},
	url = {<Go to ISI>://000233189700008},
	author = {Peng, X. J. and Sternberg, E. 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 = {<Go to ISI>://000182933200002},
	author = {Chowdhary, R. K. and Shariff, I. and Dolphin, D.}
}
@article {477,
	title = {Chiral separation of benzoporphyrin derivative mono- and diacids by laser induced fluorescence-capillary electrophoresis},
	journal = {Electrophoresis},
	volume = {23},
	number = {1},
	year = {2002},
	note = {ISI Document Delivery No.: 513ZATimes Cited: 9Cited Reference Count: 42},
	month = {Jan},
	pages = {93-101},
	type = {Article},
	abstract = {A method for the separation of benzoporphyrin derivative mono- and diacid (BPDMA, BPDDA) enantiomers; by laser induced fluorescence-capillary electrophoresis (LIF-CE) has been developed. By using 300 mm borate buffer, pH 9.2, 25 mm sodium cholate and 10\% acetronitrile as electrolyte, +10 kV electrokinetic sampling injection of 2 s and an applied +20 kV voltage across the ends of a 37 cm capillary (30 cm to the detector, 50 mum ID), all six BPD stereoisomers; were baseline-separated within 20 min. Formation constants, free electrophoretic and complexation mobilities with borate and cholate were determined based on dynamic complexation capillary electrophoresis theory. The BPD enantiomers can be quantitatively determined in the range of 10(-2)-10(-5) mg mL(-1). The correlation coefficients (r(2)) of the least-squares linear regression analysis of the BPD enantiomers are in the range of 0.9914-0.9997. Their limits of detection are 2.18-3.5 x 10(-3) mg mL(-1). The relative standard deviations for the separation were 2.90-4.64\% (n = 10). In comparison with high-performance liquid chromatography (HPLC), CE has better resolution and efficiency. This separation method was successfully applied to the BPD enantiomers obtained from a matrix of bovine serum and from liposomally formulated material as well as from studies with rat, dog and human microsomes.},
	keywords = {benzoporphyrin derivative mono- and diacids, BORATE COMPLEXATION, capillary electrophoresis, DYNAMIC COMPLEXATION MODEL, MIGRATION BEHAVIOR, PERFORMANCE LIQUID-CHROMATOGRAPHY, PHOTODYNAMIC THERAPY, PHOTOSENSITIZER, porphyrins, QUANTITATIVE DESCRIPTION, SYSTEM, TUMOR, ZONE ELECTROPHORESIS},
	isbn = {0173-0835},
	url = {<Go to ISI>://000173410100014},
	author = {Peng, X. J. and Sternberg, E. and Dolphin, D.}
}
@article {435,
	title = {Evaluation of tetraphenyl-2,3-dihydroxychlorins as potential photosensitizers},
	journal = {Journal of Porphyrins and Phthalocyanines},
	volume = {6},
	number = {2},
	year = {2002},
	note = {ISI Document Delivery No.: 595XYTimes Cited: 15Cited Reference Count: 33},
	pages = {146-155},
	type = {Article},
	abstract = {A series of beta,beta-dihydroxychlorins derived from meso-tetraphenylporphyrins (TPPs) have been synthesized. Their in vitro cytotoxicity has been measured and compared to BPDMA (verteporfin). Under the assay conditions BPDMA had an LD50 (lethal dose to kill 50\% of cells) value of 0.007 muM (5 ng/mL). The LD50 values for the TPP derivatives varied from 1.7 x 10(-2) to 9.9 muM depending upon the substituents and their position on the phenyl groups. One example of the dihydroxychlorin prepared from unsubstituted 5,15-diphenylporphyrin was examined and this exhibited an LD50 of 2.4 x 10(-3) muM! Copyright (C) 2002 Society of Porphyrins \& Phthalocyanines.},
	keywords = {AGGREGATION, BACTERIOCHLORINS, beta, beta-dihydroxychlorins, BIODISTRIBUTION, chlorins, cytotoxicity, DERIVATIVES, photodynamic, PHOTODYNAMIC THERAPY, PHOTOPHYSICAL PROPERTIES, PHOTOSENSITIZERS, porphyrins, PROTEIN-BINDING, SENSITIZERS, therapy, TUMOR PHOTOSENSITIZERS},
	isbn = {1088-4246},
	url = {<Go to ISI>://000178134600008},
	author = {Macalpine, J. K. and Boch, R. and Dolphin, D.}
}
@article {360,
	title = {Nitrogen extrusion from pyrazoline-substituted porphyrins and chlorins using long wavelength visible light},
	journal = {Chemical Communications},
	number = {22},
	year = {2002},
	note = {ISI Document Delivery No.: 618ZNTimes Cited: 20Cited Reference Count: 10},
	month = {Nov},
	pages = {2622-2623},
	type = {Article},
	abstract = {Protoporphyrin reacts with diazomethane to give pyrazolines which at long wavelength ( similar to 630 nm) extrude nitrogen to give the corresponding cyclopropyl derivatives.},
	keywords = {PHOTODYNAMIC THERAPY},
	isbn = {1359-7345},
	url = {<Go to ISI>://000179448500010},
	author = {Desjardins, A. and Flemming, J. and Sternberg, E. D. and Dolphin, D.}
}
@article {399,
	title = {Studies of a benzoporphyrin derivative with Pluronics},
	journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie},
	volume = {80},
	number = {10},
	year = {2002},
	note = {ISI Document Delivery No.: 623LCTimes Cited: 14Cited Reference Count: 22},
	month = {Oct},
	pages = {1321-1326},
	type = {Article},
	abstract = {The synthetic route for the benzoporphyrin derivatives produces two regioisomers in equimolar quantities (ring A and B isomers). A derivative of the A-ring product, BPD-MA (benzoporphyrin-derivative monoacid ring A, verteporfin), has recently been approved in North America and Europe for the treatment of age-related macular degeneration. The B-ring isomers, contrary to the A-ring isomers, exhibit high aggregation in many formulations, which results in inadequate drug delivery for clinical uses. To avoid aggregation, a non-ionic surfactant polymer such as a Pluronic - poly(ethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) - may be used as a formulation excipient. The triblock polymer investigated here is designated P123 (or poloxamer 403). When used to formulate a monoacid benzoporphyrin B-ring derivative (2), a critical micelle concentration of P123 in water occurred at approximately 0.015 to 0.03\%. The apparent pK(a) of compound 2 was dependent on its concentration in P123, and decreased as the molar ratio (P123:2) increased. High concentrations of P123 and neutral pH were found to be the best conditions to maintain the drug in its monomeric form. Kinetic studies suggest that the aggregate of 2 contains several molecules, and is formed by a catalyzed self-assembly process. Samples with 1 mg mL(-1) of drug, at pH = 7.4, and 4.8\% of Pluronic showed satisfactory capacity to load and keep monomers stable. This formulation has potential PDT applications.},
	keywords = {AGGREGATION, AQUEOUS-SOLUTIONS, block copolymers, BPD, COPOLYMERS, DYNAMICS, formulation, micelles, PHOTODYNAMIC THERAPY, photodynamic therapy (PDT), PHOTOSENSITIZERS, photosensitizing drug, Pluronic, poloxamers, porphyrins, SURFACTANTS, THERMODYNAMICS},
	isbn = {0008-4042},
	url = {<Go to ISI>://000179703700007},
	author = {Hioka, N. and Chowdhary, R. K. and Chansarkar, N. and Delmarre, D. and Sternberg, E. and Dolphin, D.}
}
@article {5046,
	title = {Aggregation studies of benzoporphyrin derivative},
	journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie},
	volume = {79},
	number = {5-6},
	year = {2001},
	note = {ISI Document Delivery No.: 456EVTimes Cited: 11Cited Reference Count: 33},
	month = {May},
	pages = {1068-1074},
	type = {Article},
	abstract = {The photophysical properties of a ring B benzoporphyrin derivative 1,3-diene dimethylester were investigated in solution (water-DMSO mixtures). At low proportions of water in DMSO, the diester obeys Beer{\textquoteright}s law at all pH values and ionic strengths investigated. For solvent systems containing more than 30\% water, the extent of deviation from Beer{\textquoteright}s law as a function of porphyrin concentration is attributed to formation of porphyrin dimers. Dimerization equilibrium constants (Kd) have been determined in different percentage of solvent mixtures, using absorption and fluorescence spectroscopies, and were found to exhibit a linear correlation between log (Kd) and the inverse of the dielectric constant (log (Kd) = 24.6 - 1060.4 x 1/epsilon (mix)). This equation permits the calculation of Kd in mixtures of water-DMSO.},
	keywords = {AGGREGATION, benzoporphyrin, BPD, DERIVATIVE, DIMERIZATION, FLUORESCENCE, PHOTODYNAMIC THERAPY, PHOTOSENSITIZERS, porphyrins, SPECTROSCOPY, therapy},
	isbn = {0008-4042},
	url = {<Go to ISI>://000170070900079},
	author = {Delmarre, D. and Hioka, N. and Boch, R. and Sternberg, E. and Dolphin, D.}
}
@article {4929,
	title = {Regioselective halogenation and palladium-catalysed couplings on 5,15-diphenylporphyrin},
	journal = {Journal of Porphyrins and Phthalocyanines},
	volume = {4},
	number = {3},
	year = {2000},
	note = {ISI Document Delivery No.: 302BXTimes Cited: 53Cited Reference Count: 13},
	month = {Apr-May},
	pages = {228-232},
	type = {Article},
	abstract = {5,15-Diphenylporphyrin was regiospecifically halogenated in high yield to give 5-iodo-15-bromo-10.20-diphenylporphyrin, which was then subjected to Heck and Stille-type coupling reactions to form unsymmetrically substituted porphyrins. The regioselectivity of the iodination of diphenylporphyrins and subsequent formation of amphiphilic porphyrins via palladium-based methodology was also studied. The utility of this method for the synthesis of photodynamic sensitisers has been demonstrated on AR4-2J rat pancreatic carcinoma cells. Copyright (C) 2000 John Wiley \& Sons, Ltd.},
	keywords = {ALKYNYLATION, amphiphiles, CROSS-COUPLING, IODINATION, palladium, PHOTODYNAMIC THERAPY, porphyrins},
	isbn = {1088-4246},
	url = {<Go to ISI>://000086346000002},
	author = {Shanmugathasan, S. and Johnson, C. K. and Edwards, C. and Matthews, E. K. and Dolphin, D. and Boyle, R. W.}
}
@article {4638,
	title = {Porphyrins incorporating heterocyclic N-oxides: (oxidopyridyl)porphyrins, porphyrin-N-oxides, and a tirapazamine-porphyrin conjugate},
	journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie},
	volume = {77},
	number = {2},
	year = {1999},
	note = {ISI Document Delivery No.: 188AZTimes Cited: 9Cited Reference Count: 41},
	month = {Feb},
	pages = {182-198},
	type = {Article},
	abstract = {{Porphyrins containing one to four 3-pyridyl groups as meso-substituents were synthesized via a mixed aldehyde condensation, and then "N-oxidized" with m-chloroperbenzoic acid to produce five novel (oxidopyridyl) porphyrins and seven porphyrin-N-oxides which were characterized by analysis and spectroscopic methods, especially NMR; an X-ray crystal structure of 5-(1-oxido-4-pyridyl)-10, 15,20-triphenylporphyrin was also obtained. Crystals of (oxidopyridyl)triphenylporphyrin are tetragonal},
	keywords = {(oxidopyridyl)porphyrins, ANTICANCER, BIOREDUCTIVE DRUGS, DESIGN, DRUGS, FUNCTIONAL-GROUPS, NICKEL(II), PHENYL, PHOTODYNAMIC THERAPY, porphyrin-N-oxides, tirapazamine},
	isbn = {0008-4042},
	url = {<Go to ISI>://000079823200003},
	author = {Posakony, J. J. and Pratt, R. C. and Rettig, S. J. and James, Brian R. and Skov, K. A.}
}
@article {4089,
	title = {Application of long-circulating liposomes to cancer photodynamic therapy},
	journal = {Biological \& Pharmaceutical Bulletin},
	volume = {20},
	number = {6},
	year = {1997},
	note = {ISI Document Delivery No.: XG547Times Cited: 26Cited Reference Count: 30},
	month = {Jun},
	pages = {670-673},
	type = {Article},
	abstract = {Photodynamic therapy (PDT) as a cancer treatment is notable for its quite low side effects in comparison with those of chemotherapy and radiotherapy. However, the accumulation of porphyrin derivatives used in PDT into tumor tissues is rather low. Since long-circulating liposomes are known to accumulate passively into tumor tissues, we liposomalized a porphyrin derivative, benzoporphyrin derivative monoacid ring A (BPD-MA), and used these liposomes to investigate the usefulness of PDT for tumor-bearing mice. BPD-MA was liposomalized into glucuronate-modified liposomes, which are known to be long-circulating. These liposomes were injected i.v. into Balb/c mice bearing Meth A sarcoma, and tumor regression and survival time were monitored after irradiation with laser light. Tumor regression and complete curing of tumor (80\% cure rate by the treatment with 6 mg/kg BPD-R?IA) were observed when long circulating liposomalized BPD-MA was injected and laser-irradiated. In contrast, only a 20\% cure rate was obtained when the animals were treated with BPD-MA solution or BPD-MA entrapped in conventional liposomes. These results suggest that a long-circulating liposomal formulation of photo-sensitive agents is useful for PDT.},
	keywords = {BEARING MICE, benzoporphyrin, BENZOPORPHYRIN DERIVATIVES, BPD, CELLS, DERIVATIVE, drug delivery system, EFFICACY, INVIVO, LIPOPROTEINS, liposome, MURINE TUMOR-MODEL, PHOTODYNAMIC THERAPY, PHOTOSENSITIZER, time},
	isbn = {0918-6158},
	url = {<Go to ISI>://A1997XG54700016},
	author = {Oku, N. and Saito, N. and Namba, Y. and Tsukada, H. and Dolphin, D. and Okada, S.}
}
@article {4063,
	title = {Chemical modification of chlorophyll a: Synthesis of new regiochemically pure benzoporphyrin and dibenzoporphyrin derivatives},
	journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie},
	volume = {75},
	number = {3},
	year = {1997},
	note = {ISI Document Delivery No.: XD813Times Cited: 10Cited Reference Count: 28},
	month = {Mar},
	pages = {262-275},
	type = {Article},
	abstract = {Starting from pheophorbide a methyl ester (5), a degradation product of chlorophyll a, routes for the preparation of 3-vinylporphyrins 6 and 9 and of an [A,C]-divinylporphyrin 16 are described. These porphyrins were obtained as a result of chemical modification of 5 on ring D and the exocyclic ring E. Diels-Alder reactions of these (di)vinylporphyrins with dimethyl acetylenedicarboxylate, to afford new regiochemically pure benzoporphyrin derivatives 29 and 30 and dibenzoporphyrin derivative 33 for potential use as sensitizers in photodynamic therapy of tumors, were also investigated.},
	keywords = {(di)benzoporphyrins, (di)vinylporphyrins, chlorins, CHLOROPHYLL, CONVERSION, Diels-Alder, ESTERS, photodynamic, PHOTODYNAMIC THERAPY, ROUTE, therapy},
	isbn = {0008-4042},
	url = {<Go to ISI>://A1997XD81300003},
	author = {Ma, L. F. and Dolphin, D.}
}
@article {4013,
	title = {Expanded porphyrins and their heterologs},
	journal = {Chemical Reviews},
	volume = {97},
	number = {6},
	year = {1997},
	note = {ISI Document Delivery No.: XZ270Times Cited: 279Cited Reference Count: 255},
	month = {Sep-Oct},
	pages = {2267-2340},
	type = {Review},
	keywords = {ACETYLENE-CUMULENE PORPHYRINOIDS, CENTERED TEMPLATE REACTIONS, COMPLEXES, DICERIUM(III) TRIS(OCTAETHYLPORPHYRINATE), ION-CONTROLLED, LOW-VALENT TITANIUM, PHOTODYNAMIC THERAPY, SCHIFF-BASE LIGANDS, TETRAPYRROLE LIGANDS, TRANSAMINATION, TRANSITION-METAL, X-ray structure},
	isbn = {0009-2665},
	url = {<Go to ISI>://A1997XZ27000011},
	author = {Jasat, A. and Dolphin, D.}
}
@article {3616,
	title = {Development and application of a nonaqueous capillary electrophoresis system for the analysis of porphyrins and their oligomers (PHOTOFRIN)},
	journal = {Analytical Biochemistry},
	volume = {241},
	number = {2},
	year = {1996},
	note = {ISI Document Delivery No.: VV144Times Cited: 34Cited Reference Count: 23},
	month = {Oct},
	pages = {143-150},
	type = {Article},
	abstract = {PHOTOFRIN is a complex porphyrin mixture used in the photodynamic therapy of cancer, A nonaqueous buffer with a polyether additive is used in the development of a capillary electrophoresis method for the analysis of this type of compound. This method achieves partial separation of 60 peaks for PHOTOFRIN in 30 min. A methanol-based buffer is used to improve the efficiency of the separation by decreasing the aggregation of porphyrin, and the resolution is improved by using the electroosmotic flow (EOF) to counterbalance the electrophoretic migration of the analytes. This counter-balancing EOF holds the analytes in the electric field longer, thereby improving the resolution, Brij 35 is used as a complexation reagent to adjust the selectivity and improve the efficiency of the separation, The effects that Brij 35 concentration has on the separation of both monomeric and oligomeric porphyrins are discussed. The polarity of the solvent is adjusted through the addition of water and its effect is rationalized. A qualitative fingerprinting method for characterizing PHOTOFRIN is developed, and different batches and stressed samples are studied. (C) 1996 Academic Press, Inc.},
	keywords = {ANIONS, FLUORESCENCE DETECTION, HEMATOPORPHYRIN, PHOTODYNAMIC THERAPY, PHOTOSENSITIZERS, POLYHEMATOPORPHYRIN, SEPARATION},
	isbn = {0003-2697},
	url = {<Go to ISI>://A1996VV14400001},
	author = {Bowser, M. T. and Sternberg, E. D. and Chen, D. D. Y.}
}
@article {3825,
	title = {Pyrrolic photosensitizers},
	journal = {Current Medicinal Chemistry},
	volume = {3},
	number = {4},
	year = {1996},
	note = {ISI Document Delivery No.: VE317Times Cited: 21Cited Reference Count: 172},
	month = {Aug},
	pages = {239-272},
	type = {Review},
	abstract = {There are three major classes of photosensitizers which can initiate a phototoxic effect to tissues upon irradiation. These are the cationic dyes (Type I Photosensitizer), the psoralens (Type I and II Photosensitizer), and cyclic polypyrrolic compounds (Type II Photosensitizer). The polypyrrolic compounds such as porphyrins have been investigated since the late 1800{\textquoteright}s for their ability to destroy tissue. In the last ten years, compounds such as chlorins and expanded porphyrins have begun to dominate the preclinical field because they can be activated with light at wavelengths tissue does not effectively absorb. The results of these investigation have been reported in more than 10,000 papers in the field covering aspects from mechanisms of action, photophysics, structure activity relationships, new compound development and clinical investigations. With the approval of PHOTOFRIN(R), (porfimer sodium), the first of the pyrrolic compounds to win acceptance by international regulatory bodies and with nearly 10 other second generation compounds undergoing early clinical trials for diseases ranging from esophageal and skin cancers to age related macular degeneration, the field of photodynamic therapy would seem to have a bright future.},
	keywords = {BENZOPORPHYRIN DERIVATIVES, capillary electrophoresis, ENDOGENOUS, M-THPC, MOUSE-TUMOR MODEL, PHOTODYNAMIC THERAPY, PHOTOFRIN-II, PLASMA-LIPOPROTEINS, PROTOPORPHYRIN, RING-A BPD, TISSUE DISTRIBUTION},
	isbn = {0929-8673},
	url = {<Go to ISI>://A1996VE31700002},
	author = {Sternberg, E. and Dolphin, D.}
}
@article {3262,
	title = {2,3-VIC-DIHYDROXY-MESO-TETRAPHENYLCHLORINS FROM THE OSMIUM-TETROXIDE OXIDATION OF MESO-TETRAPHENYLPORPHYRIN},
	journal = {Tetrahedron Letters},
	volume = {36},
	number = {19},
	year = {1995},
	note = {ISI Document Delivery No.: QY111Times Cited: 34Cited Reference Count: 25},
	month = {May},
	pages = {3295-3298},
	type = {Article},
	abstract = {meso-Tetraphenylporphyrins and meso-tetraphenylmetalloporphyrins were converted into stable 2,3-vic-dihydroxy-meso-tetraphenylchlorins and 2,3-vic-dihydroxy-meso-tetraphenylmetallochlorins by oxidation with stoichiometric amounts of OsO4 and subsequent reduction of the isolable osmate esters. The stable dihydroxychlorins were dehydrated under acid catalysis to yield 2-hydroxy-meso-tetraphenylporphyrins.},
	keywords = {BACTERIOCHLORINS, chlorins, EFFICIENT SYNTHESIS, PHOTODYNAMIC THERAPY, porphyrins, TUMOR PHOTOSENSITIZERS},
	isbn = {0040-4039},
	url = {<Go to ISI>://A1995QY11100002},
	author = {Bruckner, C. and Dolphin, D.}
}
@article {2971,
	title = {MESO-PHENYL SUBSTITUTED PORPHOCYANINES - A NEW CLASS OF FUNCTIONALIZED EXPANDED PORPHYRINS},
	journal = {Tetrahedron Letters},
	volume = {35},
	number = {30},
	year = {1994},
	note = {ISI Document Delivery No.: NY923Times Cited: 18Cited Reference Count: 11},
	month = {Jul},
	pages = {5377-5380},
	type = {Article},
	abstract = {Porphocyanines bearing phenyl substituents at both or one of the two available mesopositions have been synthesised. Derivatives have also been synthesised with substituents on the phenyl rings and both alkyl and unsubstituted pyrrolic beta-positions.},
	keywords = {BIOLOGICAL-ACTIVITIES, EXPANDED PORPHYRINS, INVITRO, PHOTODYNAMIC THERAPY, PHOTOTOXICITY, PORPHOCYANINES, TUMOR, ZINC PHTHALOCYANINES},
	isbn = {0040-4039},
	url = {<Go to ISI>://A1994NY92300015},
	author = {Boyle, R. W. and Xie, L. Y. and Dolphin, D.}
}
@article {3203,
	title = {A NEW APPROACH TO THE AROMATIC MACROCYCLE PORPHOCYANINE},
	journal = {Journal of the Chemical Society-Chemical Communications},
	number = {12},
	year = {1994},
	note = {ISI Document Delivery No.: NU725Times Cited: 12Cited Reference Count: 14},
	month = {Jun},
	pages = {1475-1476},
	type = {Article},
	abstract = {Treatment of 3,3{\textquoteright},4,4{\textquoteright}-tetraalkyl-5,5{\textquoteright}-bisformyldipyrromethanes with ammonia leads directly to the formation of an expanded tetrapyrrolic aromatic macrocyclic compound, porphocyanine.},
	keywords = {PHOTODYNAMIC THERAPY, PHOTOSENSITIZING PROPERTIES},
	isbn = {0022-4936},
	url = {<Go to ISI>://A1994NU72500036},
	author = {Xie, L. Y. and Dolphin, D.}
}
