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library design, in silico-experimental divergence
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ability to detect these aggregates is an advantage of quantitating solubility by light scattering. Prior to the Shoichet paper the detection of small aggregates by light scattering would have been viewed as a false positive, that is, as an incorrect deviation between a proper thermodynamic measurement and the result of a light-scattering measurement. After the Shoichet publication the light-scattering detection of aggregates can be viewed as an advantageous. The advantage being the ability to detect the time wasting phony HTS leads or hits. 16.9.6. Solubility Is of Low Dimensionality
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ADME and therefore solubility space is of low dimensionality. For example, if one computes the types of physicochemical properties likely to be important to oral absorption, one seldom nds more than six or perhaps seven signi cant independent properties (e.g., in a principal components analysis). Typically these are properties related to size, lipophilicity, polarity, hydrogen bonding properties, and charge status. The low dimensionality of ADME space explains the effectiveness of simple ltering algorithms like the rule of ve. The low dimensionality of ADME space contrasts with the very high dimensionality of chemistry space. For example, description of a large diverse chemical library by electrotopological parameters does not result in low dimensionality. A principal components analysis on a large diverse chemical library might nd that eight independent properties (components) derived from electrotopological properties described less than 50% of the variance in chemistry space. 16.9.7. Solubility and Permeability Interrelationships
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Poor aqueous solubility, a compound related factor rather than an assay related factor, has a major effect by introducing noise into permeability screening and hence has an effect on making computational model building very dif cult. It must be stressed that the compound solubility factor virtually never appears as an explicit consideration in the published permeability literature. Compound sets are published that are used to validate in vitro cell based absorption assays. Validation usually means obtaining an acceptable correlation between human fraction absorbed data and in vitro permeability data. The absorption data always include the experimentally very well controlled but compound number limited human fraction absorbed data that are used to de ne absorption ranges in the FDA bioavailability waiver guidelines. This limited compound set is then supplemented with additional compounds chosen from published human absorption literature. In our own work we have been able to accumulate
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solubility in the design of combinatorial libraries
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literature human fraction absorbed data on a total of about 330 compounds. Larger data sets of up to about 1000 compounds exist, which are based on published reference texts18 or intensive literature searches supplemented by detective work, to differentiate the absorption and metabolism components in oral bioavailability.19 The hallmark of compounds with human absorption data is that they are very well behaved compounds from a druglike viewpoint. The fraction absorbed is very heavily biased to the high percentage absorbed range, and the compounds are almost universally quite soluble in aqueous media. This simply re ects the compound quality ltering process that must be passed for a compound to enter the types of studies likely to generate human fraction absorbed data. In short, literature compound permeability validation sets are completely appropriate and say a lot about assay issues in a permeability screen, but they have almost no relevance to assay reproducibility issues related to poor compound solubility. Figure 16.2 sets the stage for the types of solubility among currently synthesized compounds that are likely to be submitted to a permeability screen like a Caco-2 assay. In this type of assay a variety of biological transporters are present that mediate both absorption and ef ux. The movement of a compound through the Caco-2 polarized cell layer through the action of
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mg/mL mm (MWT_300) mm (MWT_400) mm (MWT_500) mm (MWT_600) 1 3.33 2.50 2.00 1.67 3 10.00 7.50 6.00 5.00 5 16.67 12.50 10.00 8.33 10 33.33 25.00 20.00 16.67 20 66.67 50.00 40.00 33.33 30 100.00 75.00 60.00 50.00 40 133.33 100.00 80.00 66.67 50 166.67 125.00 100.00 83.33 60 200.00 150.00 120.00 100.00 70 233.33 175.00 140.00 116.67 80 266.67 200.00 160.00 133.33 90 300.00 225.00 180.00 150.00 100 333.33 250.00 200.00 166.67 200 666.67 500.00 400.00 333.33 300 1000.00 750.00 600.00 500.00 500 1666.67 1250.00 1000.00 833.33 1000 3333.33 2500.00 2000.00 1666.67
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30% of Groton cpds are in this solubility range 10% of Groton cpds are in this solubility range Solubility acceptable for 1 mg/kg potency 60% of Groton cpds are in this solubility range
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