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neglected) along with the known pKa to calculate log PN (The practice may still persist today We have intentionally omitted these simpli ed equations in this book) Most of the time this produced the correct log PN , often because ion pairing was not extensive at the pH of measurement This is true for the b blockers whose pKa is about 95; the diff 3 4 rule would suggest that ion pair partitioning should be extensive only below pH 65 With liposome partitioning, however, the rule slips to diff 1 2 This means SIP partitioning starts at about pH 85 for weak bases whose pKa values are near 95 (eg, Figs 57b, 511) So, all who published anomalous values of log PN mem may need to get out their slide rules [429 432]! (What we know now was not known then) 513 PARTITIONING INTO CHARGED LIPOSOMES
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Wunderli-Allenspach s group reported several partition studies where drugs interacted with liposomes that were charged [368,436 438] Although not entirely surprising, it was quite remarkable that propranolol partitions into negatively charged liposomes with log PN 349 and log PSIP 424 [438], compared to values mem mem determined with neutral liposome values log PN 327 and log PSIP 276 [435] mem mem Negatively charged liposomes can enhance the surface ion pair (SIP) partitioning of positively charged propranolol by a factor of 30 The unusually-shaped lipophilicity pro le is shown in Fig 511, for the system where negative charge is imparted by 24 mol% oleic acid in the eggPC
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Figure 511 Lipophilicity pro les of propranolol in liposome water (dashed curve) and liposome water, where the liposome phase had 24 mol% FFA, imparting a negative charge to the surface above pH 6 [436] [Avdeef, A, Curr Topics Med Chem, 1, 277 351 (2001) Reproduced with permission from Bentham Science Publishers, Ltd]
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Since the FFA is an anion >pH 7 and propranolol a cation <pH 9, there is a window of opportunity between pH 7 and 9 for electrostatic attraction of propranolol into the membrane phase, as indicated in Fig 511 Note how similar the curve shapes in Fig 511 are to some of the curves in Fig 46b pK mem SHIFTS IN CHARGED LIPOSOMES AND MICELLES a
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Ionizable molecules embedded in the surfaces of lipids, such as octanol (see Fig 28), liposomes (see Fig 52), or micelles, will have their apparent pKa values shifted With neutral lipids, the pKa of an acid increases and the pKa of a base decreases This is due to the effect of the decreased dielectric constant in the interfacial zone, as we have already discussed in various sections An additional (electrostatic) shift occurs if the lipid vesicles or micelles have a charged surface, according to the expression suitable for monoprotic acids and bases
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where the terms have their usual meanings, with being sign for acids, sign for bases [396,404,406, 407,448,457,458] At 25 C and using mV (millivolt) units to express the surface potential, f, the rightmost term in eq 55 becomes f/5916 The rationale for the electrostatic term goes like this: if the surface is negatively charged, then it will attract protons into the interfacial zone, such that the interfacial pH will be lower than the bulk pH, by the amount of jf=59:16j A proton fog envelops the negatively charged vesicle Since the proton concentration is in the pKa expression [Eq (31)], the apparent pKa changes accordingly Consider negatively charged liposomes made from a mixture of phosphatidylcholine (PC) and phosphatidylserine (PS) Unlike the zwitterionic head group of PC (invariant charge state, pH > 3), the head group of PS has two ionizable functions for pH > 3: the amine and the carboxylic acid In physiologically neutral solution, the PS group imparts a negative charge to the liposome (from the phosphate) Titrations of PS-containing liposomes reveal the pKa values of 55 for the carboxylic acid group and 115 for the amine group [403] When the head-group molecule itself (free of the acyl HC chains), phosphoserine (Fig 512), is titrated, the observed pKa values for the two sites are 213 and 975, respectively [162]
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