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Patent US5601802 - Administering a texaphyrin - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inAdvanced Patent SearchPatentsTexaphyrin metal complexes having improved functionalization include the addition of electron-donating groups to positions 2, 7, 12, 15, 18 and/or 21 and/or the addition of electron-withdrawing groups to positions 15 and/or 18 of the macrocycle. Electron-donating groups at positions 2, 7, 12, 15, 18...http://www.google.com/patents/US5601802?utm_source=gb-gplus-sharePatent US5601802 - Administering a texaphyrinAdvanced Patent SearchPublication numberUS5601802 APublication typeGrantApplication numberUS 08/486,886Publication dateFeb 11, 1997Filing dateJun 7, 1995Priority dateJun 2, 1995Fee statusLapsedAlso published asUS5591422, US5756726Publication number08486886, 486886, US 5601802 A, US 5601802A, US-A-5601802, US5601802 A, US5601802AInventorsGregory W. Hemmi, Jonathan L. Sessler, Tarak D. ModyOriginal AssigneePharmacyclics, Inc., Board Of Trustees, Univ. Of Tx Sys.Export CitationBiBTeX, EndNote, RefManPatent Citations (38), Non-Patent Citations (246), Referenced by (22), Classifications (17), Legal Events (5) External Links: USPTO, USPTO Assignment, EspacenetAdministering a texaphyrin
2,5-Bis[(5-benzyloxycarbonyl-4-methyl-3-methoxycarbonylethylpyrrol-2-yl)methyl]-3,4-diethylpyrrole. F3, Scheme F. In a 500 mL round bottom flask was placed 250 mL of ethanol from an unopened bottle which is purged with dry nitrogen for ten minutes. 3,4-Diethylpyrrole F2 (1.29 g, 0.01 mol) and 2-acetoxymethyl-5-benzyloxycarbonyl-4-methyl-3-methoxycarbonylethylpyrrole F1 (7.83 g, 0.02 mol) were added and the mixture heated until all of the pyrroles dissolved. p-Toluenesulfonic acid (65 mg) was added and the reaction temperature maintained at 60� C. The reaction slowly changed color from a clear yellow to a dark red with the product precipitating out of the solution as the reaction progressed. After ten hours the reaction was cooled to room temperature, the volume reduced to one half on a rotary evaporator, and then placed in the freezer for several hours. The product was collected by filtration, washed with a small amount of cold ethanol to afford 4.61 g of an off-white fine powder (61%): 1 H NMR (CDCl3, 250 MHz): δ1.14 (6H, t, CH2 CH3), 2.23 (6H, s, pyrrole-CH3), 2.31 (4H, t, CH2 CH2 CO2 CH3), 2.50 (4H, q, CH2 CH3), 2.64 (4H, t, CH2 CH2 CO2 CH3), 3.60 (10H, br s, CH3 CO2 -- and (pyrrole)2 -CH2), 4.44 (4H, br s, C6 H5 CH2), 6.99-7.02 (4H, m, aromatic), 7.22-7.26 (6H, m, aromatic), 8.72 (1H, s, NH), 10.88 (2H, br s, NH); 13 C NMR (CDCl3, 250 MHz): δ10.97, 16.78, 17.71, 19.40, 22.07, 35.09, 51.46, 65.32, 117.37, 119.34, 122.14, 126.58, 126.79, 127.36, 128.19, 133.55, 136.62, 162.35, 173.49; CI MS (M+H)+750; HRMS 749.3676 (calc. for C44 H51 N3 O8 : 749.3676).
2,5-Bis[(5-benzyloxycarbonyl-3-(3-hydroxypropyl)-4-methylpyrrol-2-yl)methyl]-3,4-diethylpyrrole. F4, Scheme F. 2,5-Bis[(5-benzyloxycarbonyl-4-methyl-3-methoxycarbonylethylpyrrol-2-yl)methyl]-3,4-diethylpyrrole F3 (5.00 g, 0.007 mol) was placed in a three necked 100 mL round bottom flask and vacuum dried for at least 30 minutes. The flask was equipped with a thermometer, an addition funnel, a nitrogen inlet tube, and a magnetic stir bar. After the tripyrrane was partially dissolved into 10 mL of dry THF, 29 mL of borane (1M BH3 in THF) was added dropwise with stirring. The reaction became mildly exothermic and was cooled with a cool water bath. The tripyrrane slowly dissolved to form a homogeneous orange solution which turned to a bright fluorescent orange color as the reaction went to completion. After stirring the reaction for one hour at room temperature, the reaction was quenched by adding methanol dropwise until the vigorous effervescence ceased. The solvents were removed under reduced pressure and the resulting white solid redissolved into CH2 Cl2. The tripyrrane was washed three times with 0.5M HCl (200 mL total), dried over anhydrous K2 CO3, filtered, and the CH2 Cl2 removed under reduced pressure until crystals of the tripyrrane just started to form. Hexanes (50 Ml) was added and the tripyrrane allowed to crystallize in the freezer for several hours. The product was filtered and again recrystallized from CH2 Cl2 /ethanol. The product was collected by filtration and vacuum dried to yield 3.69 g of an orangish white solid (76%): mp 172�-173� C.; 1 H NMR (CDCl3, 300 MHz): δ1.11 (6H, t, CH2 CH3), 1.57 (4H, p, CH2 CH2 CH2 OH), 2.23 (6H, s, pyrrole-CH3), 2.39-2.49 (8H, m, CH2 CH3 and CH2 CH2 CH2 OH), 3.50 (4H, t, CH2 CH2 CH2 OH), 3.66 (4H, s, (pyrrole)2 -CH2), 4.83 (4H, s, C6 H5 -CH2), 7.17-7.20 (4H, m, aromatic), 7.25-7.30 (6H, m, aromatic), 8.64 (1H, s, NH), 9.92 (2H, s, NH); 13 C NMR (CDCl3, 300 MHz): δ10.97, 16.72, 17.68, 20.00, 22.38, 33.22, 62.01, 65.43, 117.20, 119.75, 120.72, 122.24, 127.23, 127.62, 128.30, 132.95, 136.60, 162.13; FAB MS (M+) 693.
General procedure for the synthesis of a metal complex of texaphyrin (A7, Scheme A). One equivalent of the hydrochloride salt of the macrocycle A6, 1.5 equivalents of the M(OAc3)3 �XH2 O metal salt (where M=metal ion), and triethylamine (ca. 1 mL) are mixed together in methanol and heated to reflux under air. After completion of the reaction (as judged by the UV/vis spectrum of the reaction mixture), the solution is cooled to room temperature, the solvent is removed under reduced pressure and the crude complex dried in vacuo for several hours. A solution of dichloromethane/methanol (99:1 v/v) is added to the crude complex and the suspension is sonicated a few min. The suspension is filtered in order to remove impurities in the filtrate (incomplete oxidation products and excess triethylamine). The resulting solid is dissolved in methanol and then chloroform is added to reduce the polarity of the mixture (1:2 v/v). This solution is filtered through celite and loaded on a (pre-treated/pre-washed 1M NaNO3) neutral alumina column (10 cm). The column is first eluted with a 1:10 (v/v) methanol/chloroform solution by gravity to remove any impurity. The metal complex is then obtained by eluting the column with chloroform containing increasing amounts of methanol (20-50%). The purified lanthanide(III) texaphyrin complex is recrystallized by dissolving the complex in methanol/chloroform and carefully layering the solution with a small amount of methanol, then with diethylether. The layered solution is kept at room temperature in the dark for a few days. The texaphyrin metal complex is recrystallized twice for analytically pure measurements and characterizations.
La(OAc3)3 �6H2 O (0.814 mmol), Ce(OAc3)3 6H2 O (0.611 mmol), Pr(OAc3)3 �5H2 O (0.611 mmol), Nd(OAc3)3 �6H2 O(0.611 mmol), Sm(OAc3)3 �5H2 O (0.611 mmol), Eu(OAc3)3 �5H2 O (0.65 mmol), Gd(OAc3)3 �5H2 O (1.5 mmol), Tb(OAc3)3 �6H2 O (0.611 mmol), Dy(OAc3)3 �5H2 O (0.611 mmol), Ho(OAc3)3 �5H2 O (0.611 mmol), Er(OAc3)3 �5H2 O (0.611 mmol), Tm(OAc3)3 �5H2 O (0.611 mmol), Yb(OAc3)3 �5H2 O (0.611 mmol), or Lu(OAc3)3 �H2 O (0.611 mmol), together with TBANO3 (1.0 mmol) and triethylamine (ca. 0.5 mL) in 350 mL methanol are heated to reflux under air for 5-24 h. The workup uses the general procedure outlined above. The thulium and lutetium complexes may be more difficult to purify due to their lower solubility in methanol/chloroform solutions, which leads to a lower yield.
2,5-Bis[(3-acetoxypropyl-5-benzoyl-4-methylpyrro-2-yl)methyl]-3,4-diethylpyrrole (J2). 2,5-Bis[(3-acetoxypropyl-5-carboxyl-4-methylpyrrol-2-yl)methyl]-3,4-diethylpyrrole J1 (1.00 g, 1.67 mmol) was placed in a 100 mL three-neck round-bottom flask and dried under high vacuum for ca. 1 hr. The round-bottom flask was equipped with an argon inlet line and for magnetic stirring. At room temperature under argon, CH2 Cl2 (10 mL) was added to the flask and the resulting mixture stirred to form a suspension. Trifluoroacetic acid (2.7 mL) was then added all at once to the suspension. The tripyrrane dissolved to form a light orange solution. The reaction was stirred at room temperature under argon for ca. 45 min, after which it was cooled to 0� C. using an ice/water bath. Triethylorthobenzoate (3.8 mL) was added dropwise to the reaction with stirring over a two minute period under a flow of argon. The reaction was stirred for 40 min at 0� C. then allowed to warm to room temperature over 20 min. Water (20 mL) was added to the reaction and stirring continued for another 2 hr. Transferred reaction to a separatory funnel, separated and discarded the upper aqueous phase, and basified the lower organic layer with sat. aqueous NaHCO3 (Caution: gas evolution and frothing occurs). Separated the two layers and washed the organic phase once with sat. aqueous NaHCO3 and once with water. Dried organic phase over anhydrous MgSO4, filtered off the drying agent, removed the solvent under reduced pressure, and dried the resulting orange-red oil under high vacuum overnight. The oil was dissolved into a minimum amount of CH2 Cl2 (5-10 mL), the solution layered with hexanes (ca. 50 mL), and the tripyrrane allowed to crystallize at -20� C. The product was collected by filtration and dried under high vacuum to yield 1.06 grams of a tan solid (J2) (88%). 1 H NMR (CDCl3, 300 MHz): δ1.06 (6H, t, CH2 CH3), 1.67 (4H, p, CH2 CH2 CH2 OAc), 1.81 (6H, s, CH3 CO2 --), 2.02 (6H, s, pyrr-CH3), 2.37-2.44 (8H, m, CH2 CH3 and CH2 CH2 CH2 OAc), 3.71 (4H, s, (pyrr)2 -CH2), 3.99 (4H, t, CH2 CH2 CH2 OAc), 7.29-7.48 (10H, m, aromatic), 9.16 (1H, s, NH), 9.66 (2H, s, NH); 13 C NMR (CDCl3): δ11.8, 16.4, 17.7, 20.1, 20.9, 22.7, 29.1, 63.9, 120.9, 121.5, 127.3, 128.1, 128.2, 129.1, 130.8, 135.6, 140.1, 171.3, 185.7; FAB MS, M+ : m/e 717.
2,5-bis[(5-benzoyl-3-ethyl-4-methylpyrrol-2-yl)methyl]-3,4-diethylpyrrole (J4). 2,5-Bis[(5-carboxyl-3-ethyl-4-methylpyrrol-2-yl)methyl]-3,4-diethylpyrrole J3 (1.00 g, 2.20 mmol) was placed in a 100 mL three-neck round-bottom flask and dried under high vacuum for 1 hr. The round-bottom flask was equipped with an argon inlet line and for magnetic stirring. At room temperature under argon, CH2 Cl2 (10 mL) was added to the reaction flask and the resulting mixture stirred to form a suspension. Trifluoroacetic acid (3.5 mL) was then added all at once to the suspension. The tripyrrane dissolved to form a yellowish orange solution. The reaction was stirred at room temperature under argon for ca. 35 min, after which it was cooled to 0� C. using an ice/water bath. Triethylorthobenzoate (5.0 mL) was added dropwise to the reaction with stirring over a two minute period under a flow of argon. The reaction was stirred for 40 min at 0� C. then allowed to warm to room temperature over 20 min. Water (20 mL) was added to the reaction and stirring continued for another 1 hr. Transferred reaction to a separatory funnel, separated and discarded the upper aqueous phase, and basified the lower organic layer with sat. aqueous NaHCO3 (30 mL) (Caution: gas evolution and frothing occurs). Separated the two layers and washed the organic phase once with sat. aqueous NaHCO3 and once with water. Dried organic phase over anhydrous MgSO4, filtered off the drying agent, and removed the solvent under reduced pressure to yield a dark oil with some precipitate. The oil and solid were dissolved into a minimum mmount of CH2 Cl2 (5 mL), the solution layered with hexanes (ca. 50 mL), and the product allowed to crystallize at -20� C. The product was collected by filtration, washed with a small amount of hexanes, and dried under high vacuum to yield 0.88 grams of a tan solid (J4) (70%). 1 H NMR (CDCl3, 300 MHz): δ0.95 (6H, t, CH2 CH3), 1.05 (6H, t, CH2 CH3), 1.80 (6H, s, pyrr-CH3), 2.32-2.40 (8H, m, CH2 CH3), 3.67 (4H, s, (pyrr)2 -CH2), 7.27-7.48 (10H, m, aromatic), 9.27 (1H, s, NH), 9.66 (2H, s, NH); 13 C NMR (CDCl3): δ11.7, 15.1, 16.3, 17.1, 17.7, 22.8, 120.8, 121.4, 124.8, 127.0, 128.0(6), 128.1(4), 129.2, 130.6, 135.5, 140.2, 185.7; FAB MS, (M+H)+ : m/e 574.
4,5,9,24-Tetraethyl-16,17-dimethoxy-10,23-dimethyl-12,21-diphenyl-13,2 0,25,26,27-pentaazapentacyclo-[20.2.1.13,6.18,11 014,19 ]heptacosa-3,5,8,10,12,14,16,18,20, 22,24-undecaene (J7). 2,5-Bis[(5-benzoyl-3-ethyl-4-methylpyrrol-2-yl)methyl]-3,4-diethylpyrrole J4 (101 mg, 0.18 mmol) and 4,5-dimethoxy-1,2-phenylenediamine J5 (30 mg, 0.18 mmol) were dissolved into 200 mL of toluene and 100 mL of absolute methanol. The solvents were sparged with argon for approximately 5 min before the reaction was started. Concentrated HCl (3 drops) was then added and the reaction heated at reflux under an atmosphere of argon. After heating for ca. 2.75 days, the reaction was cooled to room temperature, the solvent removed under reduced pressure and the remaining solid dried in vacuo. The macrocycle was dissolved into CH2 Cl2 (10 mL), filtered, and the CH2 Cl2 solution layered with hexanes (80 mL). The product was allowed to slowly precipitate out of solution at -20� C. overnight. The macrocycle was collected by filtration, dissolved into a minimum amount of ethanol, and the solution layered with hexanes. The macrocycle was allowed to slowly precipitate out of solution at -20� C. for several days. The macrocycle was collected by filtration, washed with a small amount of hexanes, and dried under high vacuum to yield 28 mg of dark red product (J7). FAB MS, (M+H)+ : m/e 707.
Another means of gaining selectivity may be to covalently link the texaphyrin complex to a sapphyrin (sap) molecule, (U.S. Pat. Nos. 5,159,065; 5,120,411; 5,041,078, all incorporated by reference herein.) Since sapphyrins bind DNA, K �106 M-1, (U.S. Ser. No. 07/964,607, incorporated by reference herein) the linked texaphyrin-sapphyrin complex (txph-sap) could effectively increase the texaphyrin concentration at locations adjacent to the sapphyrin binding sites. Sapphyrins have a higher fluorescent quantum yield than texaphyrins, allowing greater fluorescence detection. A laser system may be employed where the molecules are optimized to the laser wavelength; an excited sapphyrin may transfer its energy to the conjugated texaphyrin for detection. The texaphyrin molecule may further be designed to pass through cell membranes for selective radiosensitization.
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