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dc.contributor.advisorGilmer, John
dc.contributor.authorMárquez Ruiz, Juan Francisco
dc.date.accessioned2016-12-01T12:24:51Z
dc.date.available2016-12-01T12:24:51Z
dc.date.issued2008
dc.identifier.citationJuan Francisco Márquez Ruiz, 'The design, synthesis and biological effects of novel steroid prodrugs for treatment of gastrointestinal diseases', [thesis], Trinity College (Dublin, Ireland). School of Pharmacy & Pharmaceutical Sciences, 2008, pp 222
dc.identifier.otherTHESIS 8326
dc.identifier.urihttp://hdl.handle.net/2262/78072
dc.description.abstractThe aim of the work described in this thesis was to synthesize and test the biological effects of a novel type of prodrug to deliver steroids to the colon for the treatment of gastrointestinal diseases. Glucocorticoids are used as anti-inflammatory agents in the treatment of inflammatory bowel disease. Unfortunately they undergo absorption from the GIT before reaching the colon and, as a consequence, a high number of systemic side effects are caused in patients. The prodrugs reported here are completely novel and are designed to reach the colon and exploit azoreductase and nitroreductase activity of colonic microflora to release the steroid there. Prednisolone and hydrocortisone have hydroxyl groups at positions 11, 17 and 21. Due to the different reactivity of these hydroxyl groups position 21 is favoured to undergo an esterification/lactamization. The proposed compounds have an azo group which is designed to undergo reduction in the colon liberating an anilide poised to undergo cyclization at an adjacent ester releasing the steroid. Chapter 2 describes synthetic studies directed towards candidate compounds and models for kinetic studies. Chapter 3 describes in vitro kinetic studies on the feasibility of the prodrugs and proof of concept studies in a clinically relevant model of colitis.
dc.format1 volume
dc.language.isoen
dc.publisherTrinity College (Dublin, Ireland). School of Pharmacy & Pharmaceutical Sciences
dc.relation.isversionofhttp://stella.catalogue.tcd.ie/iii/encore/record/C__Rb13251001
dc.subjectPharmacology Pharmacy, Ph.D.
dc.subjectPh.D. Trinity College Dublin
dc.titleThe design, synthesis and biological effects of novel steroid prodrugs for treatment of gastrointestinal diseases
dc.typethesis
dc.type.supercollectionthesis_dissertations
dc.type.supercollectionrefereed_publications
dc.type.qualificationlevelDoctoral
dc.type.qualificationnameDoctor of Philosophy (Ph.D.)
dc.rights.ecaccessrightsopenAccess
dc.format.extentpaginationpp 222
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