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Patent US5559207 - Texaphyrin metal complex mediated ester hydrolysis - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inPatentsA method of phosphate ester hydrolysis including incubating a solution of an aqueous phosphate ester with a texaphyrin metal complex. The metal is a metal cation having catalytic activity for ester bond hydrolysis in aqueous solution, in particular, a lanthanide metal cation, preferably Eu(III) or Dy(III)....http://www.google.com/patents/US5559207?utm_source=gb-gplus-sharePatent US5559207 - Texaphyrin metal complex mediated ester hydrolysisAdvanced Patent SearchPublication numberUS5559207 APublication typeGrantApplication numberUS 08/227,370Publication dateSep 24, 1996Filing dateApr 14, 1994Priority dateMar 6, 1989Fee statusLapsedAlso published asCA2164419A1, EP0702685A1, WO1994029316A2, WO1994029316A3Publication number08227370, 227370, US 5559207 A, US 5559207A, US-A-5559207, US5559207 A, US5559207AInventorsJonathan L. Sessler, Daniel A. Smith, Richard A. Miller, Kevin L. Ross, Meredith Wright, William C. Dow, Vladimir A. Kr al, Brent Iverson, Darren MagdaOriginal AssigneeBoard Of Regents, University Of Texas, Pharmacyclics, Inc.Export CitationBiBTeX, EndNote, RefManPatent Citations (25), Non-Patent Citations (158), Referenced by (30), Classifications (66), Legal Events (7) External Links: USPTO, USPTO Assignment, EspacenetTexaphyrin metal complex mediated ester hydrolysis
The protonated form of the macrocycle, 16-[1-(hydroxy)acetyl-2-oxy]-9,24-bis(3-hydroxypropyl)-4,5-diethyl-10,23-dimethyl-13,20,25,26,27-pentaazapentacyclo[20.2.1.13,6.18,11.0.sup.14,19 ] heptacosa-3,5,8,10,12,14(19),15,17,20,22,24-undecaene hydrochloride 2E, n=1 (500 mg, 753 μmol), europium(III) acetate pentahydrate (334 mg, 797 μmol) and triethylamine (1.33 mL, 8.0 mmol) in 150 mL of methanol were heated to reflux under air for 5.5 h. The reaction was cooled to room temperature, and stored at -20� C. overnight. Solvent was removed on a rotary evaporator, acetone (200 mL) was added, and the suspension was stirred on a rotary evaporator for 2 h. The suspension was filtered and the precipitate was dried briefly in vacuo, whereupon a solution was formed in methanol (ca. 250 mL) and water (25 mL). The pH was adjusted to 4.0 using HCl (1M), HCl-washed zeolite LZY54 was added (ca. 5 g) and the suspension was stirred on the rotary evaporator for ca. 6 h. Amberlite™ IRA-900 ion exchange resin (NaF treated, ca. 5 g) was added, and the suspension was stirred for an additional hour. The suspension was filtered, the resin was washed with methanol (ca. 100 mL), and the filtrate was adjusted to pH 4.0 using HCl (1M). Solvents were removed on a rotary evaporator, using ethanol (abs.) to remove traces of water. After drying in vacuo, the compound was dissolved in methanol (25 mL) and precipitated into rapidly stirring Et2 O (300 mL). Compound 2F, n=1 was obtained as a olive precipitate (303 mg, 48.4%) after filtering and drying in vacuo. An analytical sample was prepared by treating 50 mg of 2F, n=1 dissolved in methanol (25 mL) with acetic acid-washed zeolite, then acetic acid-washed Amberlite™ for ca. 1 h. After reducing methanol to a minimum volume, the solution was precipitated into rapidly stirring Et2 O (70 mL), filtered, and dried in vacuo. Analysis. Calculated for (C36 H39 N5 O5 Eu) (CH3 CO2) (H2 O): C, 53.66; H, 5.21, N, 8.23. Found: C, 53.39, H, 5.50, N, 8.25. HR FAB mass spectrum, M+ : Calculated for C36 H40 N5 O5 Eu, 773.2228. Found: 773.2239. UV/vis (MeOH) [λmax, nm (log ε)]: 330.0 (4.47), 464.0 (4.72), 708.0 (3.90), 762.0 (4.35).
The europium(III) complex of 16-[1-(hydroxy)acetyl-2-oxy]-9,24-bis(3-hydroxypropyl)-4,5-diethyl-10,23-dimethyl-13,20,25,26,27-pentaazapentacyclo [20.2.1.13,6.18,11.014,19 ]heptacosa-1,3,5,7,9,11(27),12,14(19),15,17,20,22(25),23-tridecaene 2F, n=1, (25 mg, 30.1 μmol) and N-hydroxysuccinimide (5 mg, 43 μmol) were dried together overnight in vacuo. The compounds were dissolved in dimethylformamide (anhydrous, 500 μL) and dicyclohexyl-carbodiimide (10 mg, 48 μmol) was added. The resulting solution was stirred under argon with protection from light for 8 h, whereupon a 110 μL aliquot was added to a solution of oligodeoxynucleotide 2G (87 nmol) in a volume of 350 μL of 0.4M sodium bicarbonate buffer in a 1.6 mL eppendorf tube. After vortexing briefly, the solution was allowed to stand for 23 h with light protection. The suspension which formed was filtered through 0.45 μm nylon microfilterfuge tubes, and the eppendorf tube was washed with 250 μL sterile water. The combined filtrates were divided into two eppendorf tubes, and glycogen (20 mg/mL, 2 μL) and sodium acetate (3M, pH 5.4, 30 μL) were added to each tube. After vortexing, ethanol (absolute, 1 mL) was added to each tube to precipitate the DNA. Ethanol was decanted following centrifugation, and the DNA was washed with an additional 1 mL aliquot of ethanol and allowed to air dry. The pellet was dissolved in 50% formamide gel loading buffer (20 μL), denatured at 90� C. for ca. 2', and loaded on a 20% denaturing polyacrylamide gel. The yellow band corresponding to conjugate 2H, n=1 (9D, 10A) was cut from the gel, crushed, and soaked in 1X TBE buffer (ca. 7 mL) for 1-2 days. The suspension was filtered through nylon filters (0.45 μm) and desalted using a Sep-pak™ reverse phase cartridge. The conjugate was eluted from the cartridge using 40% acetonitrile, lyophilized overnight, and dissolved in 1 mM HEPES buffer, pH 7.0 (500 μL). The solution concentration determined using UV/vis spectroscopy (calculated ε260 =187,110) was 21.6 μM in conjugate 2H, n=1 (9D, 10A) (12%).
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for treating vascular inflammation* Cited by examinerClassifications U.S. Classification530/300, 530/387.1, 435/135, 534/16, 435/91.1, 536/23.1, 536/1.11, 534/15, 435/155, 534/11International ClassificationC07F9/6558, C07B61/00, C07F9/06, C07F9/6561, C07D487/22, C07H21/00, B01J31/18, A61K41/00, A61L2/00, A61K49/06, A61K49/00, A61K51/04, A61K47/48, A61K49/08, B01J31/16, B01J31/06Cooperative ClassificationB01J31/1658, A61K41/0076, B01J2531/23, B01J31/061, A61L2/0011, B01J2531/26, A61K47/48069, B01J2531/72, B01J2531/38, B01J31/1815, A61K49/0036, B01J2531/025, A61K49/126, B01J2531/842, B01J2531/96, B01J2531/28, B01J2531/847, A61K49/085, B01J2531/845, A61K49/106, C07H21/00, A61K51/0485, A61K49/0021, B01J2531/27, A61K41/0038, C07D487/22European ClassificationA61K41/00W10, A61K49/10C8, A61K49/12P, C07H21/00, A61K49/00P4F4C12, B01J31/16D2, A61K49/08Z, A61K47/48H4H4, B01J31/18B2B, A61L2/00P2, A61K41/00P, A61K51/04L16, A61K49/00P4F4C, C07D487/22Legal EventsDateCodeEventDescriptionAug 15, 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