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511 THREE INDICES OF LIPOPHILICITY: LIPOSOMES, IAM, AND OCTANOL Taillardat-Bertschinger et al [311] explored the molecular factors in uencing retention of drugs on IAM columns, compared to partitioning in liposomes and octanol Twenty- ve molecules from two congeneric series (b-blockers and ( p-methylbenzyl)alkylamines; see Fig 55) and a set of structurally unrelated drugs were used Liposome-buffer partitioning was determined by the equilibrium dialysis and the pH-metric methods The intermethod agreement was good, with r 2 087

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r2=087 s=063 n=9 pKamem = 117 pKaOCT - 368

Figure 510 Comparison of membrane to octanol pKa values of compounds with unrelated structures [149,385,386] [Avdeef, A, Curr Topics Med Chem, 1, 277 351 (2001) Reproduced with permission from Bentham Science Publishers, Ltd]

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7:0 However, when the IAM log kIAMw were compared to liposome log Dmem, 70, there was no direct correlation when all of the compounds were used It was clear that multi mechanisms were operative, in the Lipinski sense [1] For the series of large molecules, such as, b blockers or the long-chain (p-methylbenzyl)alkylamines, IAM retention correlated with liposome partitioning Hydrophobic recognition forces was thought to be responsible for the partitioning process In addition, the formation of an H bond between the hydroxy group of the b blocker and the ester bond of phospholipids (Fig 51) may explain why the b blockers partitioned into the liposomes more strongly than the alkylamines For the more hydrophilic short-chain (p-methylbenzyl)alkylamines (n 0 3 in Fig 55), the balance between electrostatic and hydrophilic interactions was different in the IAM and liposome systems Electrostatic interactions are thought to play only a minor role for the IAM retention of the model solutes, presumably due to the smaller density of phospholipids in IAM resin surfaces, compared to liposomes The solute s capacity to form H-bonds, which is important for partitioning in liposomes, plays only a minor role in the IAM system

Public Information Distribution System The Sarbanes-Oxley requirements regarding public distribution of information can be taken care of by deploying enterprise information portal systems These portals can disburse information to the appropriate stakeholders and investors, as well as to regulatory authorities The portals do the job of publishing the appropriate documents and real-time alerts through proper access control systems, after going through the predefined approval hierarchy, by posting them automatically on to the enterprise web sites on the Internet and any intranets Most portal systems also allow automatic notification e-mails and short message service (SMS) alerts to be sent to subscribed users A simplified alternative is to have a basic web site where important information is published, and through which e-mail notifications to various agencies and regulatory authorities are sent, in addition to electronic and hard-copy filings Further, notification of investors and stakeholders via e-mail newsletters can also fulfill several important requirements of Sarbanes-Oxley

512 GETTING IT WRONG FROM ONE-POINT log Dmem MEASUREMENT In the early literature, it was a common practice to make a single measurement of log D, usually at pH 74, and use a simpli ed version of Eq (410) (with log PI

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