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Figure 512 Phosphoserine
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According to the diff 1 2 rule, we should have expected to see the pKa 413 (carboxylate) and 875 (amine), but the liposome titration shows something else Instead, we have an anomalous additional shift of 137 for the carboxylic group and a 275 for the amine group These extra shifts are due to the negatively charged surface of the liposomes! We can estimate, using Eq (55), that when the carboxylic group is titrated in the PS liposome, the surface charge is 81 mV (pH 55), and when the amine group is titrated, the surface charge drops to 163 mV (pH 115) Conversely, if we had a way of estimating surface charge,
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Critically Selected Experimental Liposome Water Partition Coef cients log PN mem 239 317 240 170 250 180 429 220 400 540 434 230 300 300 387 239 200 370 189 180 300 370 170 238 345 340 500 323 346 330 190 180 log PSIP mem 248 166 160 200 270 160 429 100 420 445 266 170 220 190 194 122 125 290 102 130 280 270 120 076 261 350 300 211 138 170 240 140 ta ( C) 37 37 37 37 37 37 37 37 37 37 37 37 37 37 37 37 37 37 Ref 149 149 385 385 385 385 b 385 b b 149 385 385 385 149 149 385 385 b 385 385 385 385 149 149 385 385 149 149 385 385 385
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4-Phenylbutylamine 5-Phenylvaleric acid Acetylsalicylic acid Acyclovir Allopurinol Amiloride Amlodipine Atenolol Carvedilol Chlorpromazine Diclofenac Famotidine Fluoxetine Furosemide Ibuprofen Lidocaine Metoprolol Miconazole Morphine Moxonidine Nizatidine Olanzapine Paromomycin Procaine Propranolol Rifabutine Terbina ne Tetracaine Warfarin Xipamide Zidovudine Zopiclone
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Temperature 25 C, unless otherwise stated Sirius Analytical Instrument Ltd
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PARTITIONING INTO LIPOSOMES
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TABLE 54 Liposome Water Partition Coef cients of Substituted Phenols and Other Compounds Compound Phenol 2-Cl-phenol 3-Cl-phenol 4-Cl-phenol 2,4-Di-Cl-phenol 2,6-Di-Cl-phenol 3,4-Di-Cl-phenol 2,4,5-Tri-Cl-phenol 2,4,6-Tri-Cl-phenol 3,4,5-Tri-Cl-phenol 2,3,4,5-Tetra-Cl-phenol 2,3,4,6-Tetra-Cl-phenol penta-Cl-phenol 2-NO2-phenol 4-NO2-phenol 2,4-Di-NO2-phenol 2,6-Di-NO2-phenol 2-Me-4,6-di-NO2-phenol 4-Me-2,6-di-NO2-phenol 2-s-Bu-4,6-di-NO2-phenol 2-t-Bu-4,6-di-NO2-phenol 4-t-Bu-2,6-di-NO2-phenol 2-Me-phenol 3-Me-phenol 4-Me-phenol 2-Et-phenol 4-Et-phenol 2-Pr-phenol 4-Pr-phenol 2-s-Bu-phenol 4-s-Bu-phenol 2-t-Bu-phenol 3-t-Bu-phenol 4-t-Bu-phenol 2-Ph-phenol 4-Ph-phenol 4-t-Pent-phenol 2,6-di-Me-phenol 2,6-di-Et-phenol 3-Me-4-Cl-phenol 4-SO2Me-phenol 4-CN-phenol 4-CF3-phenol 3-NO2-phenol log PN mem 197 278 278 292 354 283 382 435 382 472 488 446 517 209 272 273 194 269 234 374 410 379 245 234 242 281 288 313 309 347 343 351 325 343 340 324 364 247 273 329 127 211 325 256 log PSIP mem 157 243 241 109 282 280 259 318 363 339 379 070 095 194 184 246 226 333 354 321 Note/Ref a a;b a a;b a;b a;b b b a;b b b b b b b a;b b a;b b a;b b b a a a a a a a a a a a a a a a a a a a a a a
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(Continued) log PN mem 302 314 082 104 171 199 288 278 375 309 021 088 091 098 104 105 132 160 176 181 190 191 201 210 220 221 260 260 261 271 275 375 295 241 185 log PSIP mem 136 146 150 375 050 212 Note/Ref a a c c c c c c c c c c c c c c c c c c c c c c c c c c c c c c c c;d e e e e
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2-Et-4,6-di-NO2-phenol 2-i-Pr-4,6-di-NO2-phenol Benzenesulphonamide Aniline Nitrobenzene Naphthylamide 4-Cl-1-naphthol Naphthalene 2-Me-anthracene 1,2,5,6-Dibenzanthracene Benzamide Methylphenylsulphone Hydrochlorothiazide Methylphenylsulphoxide Phenylurea Phenylbenzamide Phenol Dimethylphenylsulfonamide Acetophenone Benzonitrile Benzaldehyde Methylnaphthylsulphone Naphthylsulphonamide Anisole Methylbenzoate Triphenylphosphineoxide 3-(2-Naphthoxy)propylmethylsulphoxide Chrysene Fluoroanthrene Toluene Phenanthrene Atenolol Xamoterol Proxichromil Amlodipine 5-Phenylvaleric acid 4-Phenylbutylamine 5-Hydroxyquinoline
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Temperature 25 C, equilibrium dialysis, small unilamellar vesicles (lecithin) [381] Temperature 20 C, equilibrium dialysis, small unilamellar vesicles (DOPC), 01 M KCl [382] c Centrifugation method (15 min, 150,000 g), brush-border membrane vesicles [433] d Ionic strength 0015 M (NaCl) e Temperature 37 C, 002 M ionic strength, ultra ltration method, small unilamellar vesicles (DMPC) [441]
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