high-throughput determination of log D values by lc/ms method in Visual Studio .NET

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50000 Generic APCI: y = 3545x - 247 R2 = 0.9998 40000 Peak Area x 10^(-3)
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20000 ESI: y = 386x + 319 R2 = 0.9712
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0 0 2 4 6 8 Lidocaine (mM) 10 12 14
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B 100000 R2 = 0.9902 R2 = 0.9834 50000 R2 = 0.9999 25000
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0 0 THRX-185463 THRX-784558 THRX-102200 10 20 30 40 50 mM compound
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Figure 17.6. Relationship between peak area and the concentrations of compounds by LC/APCI-MS. (A) Lidocaine between 0.1 and 12.5 mM; (B) Threravance compounds between 0.25 and 32 mM.
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randomly picked compounds, THRX-784558, THRX-185463, and THRX102200 are linear (R2 > 0.98) within the tested range of 0.25 to 32 mM (128fold). This more than two-orders of magnitude linear range is wide enough for quantitative analysis, and the analysis can proceed without constructing a standard response curve rst if concentrations of compounds in the two phases can be adjusted to within the range.
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results and discussion 17.3.3.
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Dilution Strategy for Log D Determination by LC/APCI-MS
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The major objective of the current study was to increase throughput of the assay. Ideally a single linear response curve could be constructed to quantitate various analytes over a broad range of concentrations. Unfortunately, MS responses vary from compound to compound, making it impossible to construct a universal response curve for multiple compounds. Fortunately, determination of the absolute concentrations of the compound is not necessary, which would require an absolute calibration curve for each compound. Rather, the goal is to nd the ratio of the concentrations of the compound in two phases. As long as the concentrations of the compound in the two phases are within the linear range, the log D value can be determined, as the LC has already taken care of the difference in the sample matrix (i.e., octanol vs. buffer). A new dilution strategy was developed to bring the sample concentrations in the two phases as close as possible. After dilution, the nal concentrations of the analyte usually are less than 20 mM, which is within the linear range for most compounds. Thus errors associated with the nonlinearity of the response curves will be minimal in determining the log D values. In order improve throughput, c log D values for in-house compounds were used as a guidance in the selection of dilution factors. For compounds with -2 c log D 2, only 1 mL of compound stock solution (20 mM) was added into a total of 1 mL octanol and aqueous buffer mixture (1 : 1), and both phases were analyzed directly without any dilution. If c log D < -2 or > 2, 10 mL of stock solution was used, and the aqueous or octanol phases, respectively, were diluted 100-fold before analysis by LC/MS. Thus the combination of using c log D values for references and performing limited dilutions has enabled generation of experimental log D values with a minimum lab work. In 96-well plate based sample preparations, a similar dilution strategy was used to generate the log D data.
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High-Throughput Working Process
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Figure 17.2 depicts the proposed working process for the high-throughput log D determination prior to implementing this work in the lab. During the course of the work, modi cations were made to make the process work smoothly. The nal process is described in Figure 17.7. Two mmoles each of the compounds to be evaluated are submitted in 96-well plates (Matrix Technologies, Hudson, NH). These plates have removable wells that can be
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high-throughput determination of log D values by lc/ms method
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A : Com pound B : P os itio n C : Bar code D: c Log D E : C a lc u la te d d ilu tio n fa c to r
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