Chiral separation of benzoporphyrin derivative mono-and...

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Reexamination Certificate

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Reexamination Certificate

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06878253

ABSTRACT:
A method for the separation of benzoporphyrin derivative mono and diacid (BPD-MA, BPD-DA) enantiomers by Laser-Induced Fluorescence Capillary Electrophoresis has been developed. The limits of detection are 2.06×10−6M, and the relative standard deviation for the separation was 2.90% to 4.64%. The BPD enantiomers can be quantitatively determined in the range of 10−2to 10−5mg mL−1. In comparison with 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.

REFERENCES:
patent: 5171749 (1992-12-01), Levy et al.
patent: 5626757 (1997-05-01), Armstrong
patent: 6331235 (2001-12-01), Dolphin et al.
patent: 4136462 (1993-05-01), None
patent: 0485370 (1992-05-01), None
patent: 546916 (1993-06-01), None
Page 107 or Organic Stereochemistry, Henri Kaga, John Wiley & Sons, 1978.*
Pages 106-107 and 1026 of the Concise Encylopedia of Chemistry, translated and revised by Mary Eagleson, Walter de Gruyter, 1994.*
“Conformer” definition downloaded from the on-line version of the IUPAC Compendium of Chemical Terminology, (1997), 2nd ed., www.iupac.org/goldbook/CO1262.pdf.*
“Atropisomers” definition downloaded from the on-line version of the IUPAC Compendium of Chemical Terminology, (1997), 2nded. www.iupac.org/goldbook/A00511.pdf.*
Kaufmann et al. Separation of the Rotational Isomers of Tetrakis (N-methyl-2-pyridiniumyl)porphyrin and Crystal Structure of alpha,alpha,alpha,Beta-(Tetrakis(N-methyl-2-pyridiniumyl)porphyrin)copper Hexacyanoferrate, inorg. Chem. 1995, 34, 5073-5079.*
Fanali et al. The utility of cyclodextrins in capillary electrophoresis.J. Cap. Elec.001:1 (1994).
Stalcup et al., Heparin: A Chiral Mobile-Phase Additive for Capillary Zone Electrophoresis.Anal. Chem.66, 3054-3059 (1994).
Wu et al., Separation of Porphyrins Using a γ-Cyclodextrin Stationary Phase.Journal of Liquid Chromatography,17(5), 1111-1124 (1994).
Armstrong et al.,Derivatized Cyclodextrins Immobilized on Fused-Silica Capillaries for Enantiomeric Separations Via Capillaries for Enantiomeric Separations Via Electrophoresis, Gas Chromatography, or Supercritical Chromatography.Anal. Chem. (1993) 65(8):1114-17.
Aveline, B. M. et al.,The Effects Of Aggregation, Protein Binding And Cellular Incorporation On The Photophysical Properties Of Benzoporphyrin Derivative Monoacid Ring A(BPDMA), J. Photochem. Photobiol. Biology (1995) 30:161-69.
Beukeveld, G. J. J. et al.,Determination Of Porphyrins In Bile Using High Performance Liquid Chromatography and Some Clinical Applications,Eur. J. Clin. Chem. Clin. Biochem. (1994) 32:153-59.
Böeseken, J.,The Use Of Boric Acid For The Determination of The Configuration Of Carbohydrates,ADV. Carbohydr. Chem. (1949) 32:153-59.
Bowser, M. T. et al.,Development And Application Of a Nonaqueous Capillary Electrophoresis System For The Analysis Of Porphyrins And Their Oligomers(PHOTOFRIN), Analytical Biochemistry (1996) 241:143-50.
Bowser, M. T. et al.,Quantitative Descripton Of Migration Behavior Of Porphyrins Based On The Dynamic Complexation Model In A Nonaqueous Capillary Electrophoresis System,Electrophoresis (1997) 18:82-91.
Caplus Abstract of Wu et al.Separation of Porphyrins Using A. Gamma. -Cyclodextrin Stationary Phase,J. Liq. Chromogr. (1994) 1795:1111-24.
Caplus Abstract of Fanali et al.The Utility of Cyclodextrins in Capillary Electrophoresis.J. Capillary Electrophor. (1994) 1(1):72-78.
Chan et al.Capillary Electrophoresis Analysis of Polyhaematoporphyrin, A Photosensitizer Used in Photodynamic Therapy.Journal of Chromatography (1993) 636:171-178.
Consden, R. et al.,Ionophoresis Of Sugars On Paper And Some Applications To The Analysis Of Protein Polysaccharide Complexes,Nature (1952) 169:783-85 May 10, 1952.
Delaney, T. F. et al.,Photodynamic Therapy Of Cancer,Comprehensive Therapy (1988) 14 (5):43-55 May.
Dixon et al.Capillary Electrophoretic Separation of Cationic Porphyrins,Hournal of Chromatography A (1998) 802:367-380.
Hjertén, S.,Free Zone Electrophoresis,Chromatog. Rev. (1967) 9:122-219.
Ho, J. W. et al.,Effects Of Injection Solvents On The Separation Of Porphyrin And Metalloporphyrin In Reversed-Phase Liquid Chromatography,J. Liq. Chromatogr. (1994) 17(3):549-58.
Hoffstetter-Kuhn, S. et al.,Influence Of Borate Complexatin On The Electrophoretic Behavior Of Carbohydrates In Capillary Electrophoresis,Anal. Chem. (1991) 63:1541-47 Aug. 1, 1991.
Honda, S. et al.,Simultaneous Determination Of Reducing Monosaccharides By Capillary Zone Electrophoresis As The Borate Complexes Of N-2-Pyridylglycamines,Analytical Biochemistry (1989) 176:72-77.
Honda, S. et al.,Analysis Of The Oligosaccharides In Ovalbumin By High-Performance Capillary Electrophoresis,Analytical Biochemistry (1990) 191:228-34.
Jamieson, C. H. M. et al.,Preferential Uptake Of Benzoporphyrin Derivative By Leukemic Versus Normal Cells,Leukemia Research (1990) 14(3):209-19.
Jorgenson, J. W. et al.,Free Zone Electrophoresis In Glass Capillaries,Clin. Chem. (1981) 27(9):1551-53.
Kimmett, S. M.Evidence For The Stereoselective Inhibition Of Chick Embryo Hepatic Ferrochelatase By N-Alkylated Porphyrins. II,Molecular Pharmacology (1992) 42:307-10.
Landers, J. P. et al.,Separation Of Boron-Complexed Diol Compounds Using High-Performance Capillary Electrophoresis,Anal. Chem. (1992) 64:2846-51 Nov. 15, 1992.
Lim, C. K. et al.,High-Performance Liquid Chromatography Of Porphyrins,J. Chromatogr. (1988) 429:123-53.
Liu, X. et al.,Capillary Electrophoresis Enzyme Immunoassay For Digoxin In Human Serum,Anal. Chem. (1995) 67:3211-18 Sep. 15, 1995.
Miller, H. et al.,Photodynamic Therapy Of Subretinal Neovascularization In The Monkey Eye,Arch. Opthalmol. (1993) 111:855-60 Jun.
Morin, P. et al.,Borate Complexation Of Flavonoid-O-Glycosides In Capillary Electrophoresis.J. Chromatogr. (1993) 628:161-69 Jan. 01, 1993.
Neyndorff, H. C. et al.,Development Of A Model To Demonstrate Photosensitizer-mediated Viral Inactivation In Blood,Transfusion (1990) 30(6):485-90.
Owens, J. W. et al.,Chromatographic Analysis Of Photodynamically Significant Porphyrin Dimers And Trimers,J. Chromatogr. B (1996) 682:327-36 Jul. 12, 1996.
Peng, X. et al.,Quantitative Description Of Analyte Migration Behavior Based On Dynamic Complexation In Capillary Electrophoresis With One Or More Additives,Electrophoresis (1997) 18:706-16.
Penn, S. G. et al.,Capillary Electrophoresis With Chiral Selectors: Optimization Of Separation And Determination Of Thermodynamic Parameters For Binding Of Tioconazole Enantiomers To Cyclodextrins,Anal. Chem. (1994) 66:2866-73 Sep. 15, 1994.
Pietta, P. et al.,Influence Of Structure On The Behavior Of Flavonoids In Capillary Electrphoresis,Electrophoresis (1994) 15:1326-31.
Richter, A. M. et al.,Biodistribution Of Tritiated Benzoporphyrin Derivative(3H-BPD-MA),A New Potent Photosensitizer, In Normal And Tumor-Bearing Mice,J. Photochem. Photobiol. B Biology (1990) 5:231-44 Apr. 15, 1990.
Richter, A. M. et al.,Photosensitizing Efficiency Of Two Regioisomers Of The Benzoporphyrin Derivative Monoacid Ring A(BPD-MA), Biochemical Pharmacology (1992) 43(11):2349-58.
Richter, A. M. et al.,Preliminary Studies on a More Effective Phototoxic Agent Than Hematoporphyrin,J. Natl. Can. Inst. (1987) 79(6):1327-32.
Richter, A. M. et al.,Characterization Of Benzoporphyrin Derivative, A New Photosensitizer,Proceeding SPIE, The International Society for Optical Engineering, Boston, MA (1988) 997:132-38.
Richter, A. M. et al.,Photosensitising Potency of Structural Analogues Of Benzoporphyrin Derivative(BPD)In A Mouse Tumour Model,Br. J. Cancer (1991) 63:87-93.
Sato, H. et al.,Simultaneous Separation And Quantification Of Free And Metal- Chelated Protoporphyrins In Blood By Three-Dimensional HPLC,Clin. Chem. (1994) 40(7):1239-44.
Sternberg, E. et al,Pyrrolic Photosensitizers,Current Medicinal Chemistry (1996) 3:239-72.
Udagawa, M. et al.,Determination Of Coporporphyrin I and III Isomers By

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