Page 1 |
Save page Remove page | Previous | 1 of 63 | Next |
|
small (250x250 max)
medium (500x500 max)
large ( > 500x500)
Full Resolution
All (PDF)
|
This page
All
Subset |
SYNTHESES OF P-O-C LINKED FOSCARNET-PEPTIDE CONJUGATES
by
Chi Vu Hue Pham
A Thesis Presented to the
FACULTY OF THE GRADUATE SCHOOL
UNIVERSITY OF SOUTHERN CALIFONIA
In Partial Fulfillment of the
Requirements for the Degree
MASTER OF SCIENCE
(CHEMISTRY)
December 2009
Copyright 2009 Chi Vu Hue Pham
Object Description
| Title | Syntheses of P-O-C linked foscarnet-peptide conjugates |
| Author | Pham, Chi Vu Hue |
| Author email | chivpham@usc.edu; chiduy2001@yahoo.com |
| Degree | Master of Science |
| Document type | Thesis |
| Degree program | Chemistry |
| School | College of Letters, Arts and Sciences |
| Date defended/completed | 2009-07-27 |
| Date submitted | 2009 |
| Restricted until | Unrestricted |
| Date published | 2009-10-08 |
| Advisor (committee chair) | McKenna, Charles |
| Advisor (committee member) |
Brutchey, Richard Qin, Peter Shen, Wei-Chiang |
| Abstract | The trisodium salt of phosphonoformic acid (PFA), foscarnet, is an analogue of pyrophosphate that inhibits a broad spectrum of viruses. A long-recognized limitation of foscarnet has been its very low oral bioavailability, which is due to the ionization of PFA at physiological pH. As a result, in the clinic it can only be administered intravenously. Many prodrug approaches have been investigated to circumvent the issues associated with the bioavailability and permeability of phosphonoformate. Here, we report the synthesis of a series of novel PFA prodrugs, created by incorporation of toxicologically benign amino acids or small peptides to abate the anionic state of the drug. In this work, conjugates of PFA monosalts were esterified by the alcohol side-chain group of serine using Mitsunobu chemistry to create the P-O-C link. These amino acid conjugates are potential substrates for human intestinal peptide transporter (hPepT1). |
| Keyword | phosphonoformic acid; PFA; prodrugs; prodrugs synthesis |
| Language | English |
| Part of collection | University of Southern California dissertations and theses |
| Publisher (of the original version) | University of Southern California |
| Place of publication (of the original version) | Los Angeles, California |
| Publisher (of the digital version) | University of Southern California. Libraries |
| Provenance | Electronically uploaded by the author |
| Type | texts |
| Legacy record ID | usctheses-m2653 |
| Rights | Pham, Chi Vu Hue |
| Repository name | Libraries, University of Southern California |
| Repository address | Los Angeles, California |
| Repository email | http://www.usc.edu/isd/libraries/services/ask_a_librarian/email/ |
| Filename | etd-Pham-3198 |
| Archival file | uscthesesreloadpub_Volume48/etd-Pham-3198.pdf |
Description
| Title | Page 1 |
| Full text | SYNTHESES OF P-O-C LINKED FOSCARNET-PEPTIDE CONJUGATES by Chi Vu Hue Pham A Thesis Presented to the FACULTY OF THE GRADUATE SCHOOL UNIVERSITY OF SOUTHERN CALIFONIA In Partial Fulfillment of the Requirements for the Degree MASTER OF SCIENCE (CHEMISTRY) December 2009 Copyright 2009 Chi Vu Hue Pham |
Comments
Post a Comment for Page 1
