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Date of Award


Document Type

Thesis - Pacific Access Restricted

Degree Name

Master of Science (M.S.)



First Advisor

Patrick R. Jones

First Committee Member

Michael J. Minch

Second Committee Member

Charles A. Matuszak

Third Committee Member

Silvio Rodriguez

Fourth Committee Member

Timothy Smith


Methods were developed for the detection and quantification of the sulfone drug, 4,4'-diaminodiphenyl sulfone, or dapsone (DDS) and its metabolites, monoacetyldapsone (MAD) and diacetyldapsone (DAD). The work involved the synthesis of those two metabolites; confirmation of them by NMR and mass spectrometry; separation and identification of mixtures of DDS, MAD and DAD using HPLC with a uv detector and/or a mass spectrometric detector. The HPLC was operated at 1 m1/min at 285 nm, using a C-18 reversed-phase column (AXXI CHROM, 5 micron, 25cm x 2.1mm). The isochratic mobile phase consisted of 67% aqueous pH 6 phosphate buffer, 23% acetonitrile and 10% methanol, or 23% acetonitrile and 77% water. The limit of determination using a 5 pl sample was 0.2 pg/ml (0.004 nmole) for DDS, 0.3 pg/ml (0.005 nmole) for MAD and 0.4pg/ml (0.006 nmole) for DAD.

The LC/MS work was done using an electrospray interface between the HPLC and the quadrupole mass spectrometer. The LC/MS method gave crucial information to confirm the identity of the three compounds measured.

Overall, a combination of the two techniques is a superior approach for the determination of DDS and its metabolites with the MS confirming the identity of the metabolites and the HPLC separating and quantitating the analyses. Since only a small amount of sample is required in the experiment, these methods could be applied in studies involving analysis of metabolites from urine and plasma, facilitating future pharmacokinetics analysis of DDS and its metabolites.



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