soft alkyl ether prodrugs of a model phenolic drug the effect of incorporation of ethyleneoxy groups on transdermal delivery软烷基醚高活性酚醛模型药物的效果的皮肤ethyleneoxy组织交付.pdfVIP

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soft alkyl ether prodrugs of a model phenolic drug the effect of incorporation of ethyleneoxy groups on transdermal delivery软烷基醚高活性酚醛模型药物的效果的皮肤ethyleneoxy组织交付.pdf

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soft alkyl ether prodrugs of a model phenolic drug the effect of incorporation of ethyleneoxy groups on transdermal delivery软烷基醚高活性酚醛模型药物的效果的皮肤ethyleneoxy组织交付

Molecules 2009, 14, 4231-4245; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Soft Alkyl Ether Prodrugs of a Model Phenolic Drug: The Effect of Incorporation of Ethyleneoxy Groups on Transdermal Delivery Joshua Denver Thomas 1, Susruta Majumdar 2 and Kenneth Berry Sloan 3,* 1 Laboratory of Medicinal Chemistry, NCI, NIH, NCI – Frederick, Frederick, MD 21702, USA 2 Laboratory of Molecular Pharmacology and Chemistry, Memorial Sloan Kettering Cancer Center, 1275 York Ave, New York, NY 10021, USA 3 Department of Medicinal Chemistry, University of Florida, P.O. Box 100485, Gainesville, FL 32610, USA * Author to whom correspondence should be addressed; E-Mail: sloan@; Tel.: +1-352-273-7745; Fax: +1-352-392-9455. Received: 18 September 2009; in revised form: 13 October 2009 / Accepted: 19 October 2009 / Published: 22 October 2009 Abstract: Two different types of soft alkyl ether prodrugs incorporating ethyleneoxy groups into the promoiety have been synthesized for a model phenol (acetaminophen, APAP): alkyloxycarbonyloxymethyl type (AOCOM) and N-alkyl-N-alkyloxycarbonyl- aminomethyl type (NANAOCAM). The solubilities in isopropyl myristate, SIPM, and water, SAQ, partition coefficients between IPM and pH 4.0 buffer, KIPM:4.0, and the delivery of total species containing APAP through hairless mouse skin from IPM, JMMIPM, have been measured for the prodrugs. The JMMIPM values were accurately p