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dc.contributor.authorBulmer, AC
dc.contributor.authorBlanchfield, JT
dc.contributor.authorCoombes, JS
dc.contributor.authorToth, I
dc.date.accessioned2017-05-03T16:59:40Z
dc.date.available2017-05-03T16:59:40Z
dc.date.issued2008
dc.date.modified2009-12-11T06:43:56Z
dc.identifier.issn0968-0896
dc.identifier.doi10.1016/j.bmc.2008.02.008
dc.identifier.urihttp://hdl.handle.net/10072/27343
dc.description.abstractBile pigments, including bilirubin and biliverdin are tetrapyrrolic, dicarboxylic acids capable of forming conjugates at their propionic acid groups via ester or amide bonds. They possess substantial antioxidant and anti-mutagenic activities and therefore their intestinal absorption might influence the development of cardiovascular disease and cancer. The aim of this study was to investigate whether altering the physico-chemical properties of bile pigments would improve their permeability in an in vitro assay of absorption. Native and synthetically modified bile pigments were tested for gastrointestinal permeability and metabolic stability using the Caco-2 cell line. In addition, a gross measure of their toxic effects was tested in a red blood cell co-incubation assay. The apparent permeability of unconjugated bilirubin (1), bilirubin ditaurate (2) and biliverdin (3) through Caco-2 cell monolayers was determined to be 10.4 ᠱ.2 נ10-7, 35.2 ᠳ.4 נ10-7 and 37.0 ᠱ.6 נ10-7 cm/s (mean ᠓D), respectively, while biliverdin diglucosamine (4), and biliverdin dioctylamine (5) were impermeable. Unconjugated bilirubin, biliverdin, bilirubin ditaurate and biliverdin diglucosamine did not decompose when incubated in Caco-2 cell homogenates, whereas biliverdin dioctylamine decomposed over time. Only unconjugated bilirubin showed toxicity towards red blood cells (1000 卩, an effect that was abolished by the addition of 40 g/L serum albumin. The data presented here suggest that bile pigments are absorbed across the Caco-2 cell monolayer and that conjugation of biliverdin to hydrophilic or lipophilic moieties decreases their absorption and can reduce their metabolic stability. In summary, exogenous bilirubin and biliverdin supplements could be absorbed across the intestinal epithelium in vivo and potentially increase circulating concentrations of these antioxidant compounds.
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.languageEnglish
dc.language.isoeng
dc.publisherPergamon Press
dc.publisher.placeOxford, UK
dc.publisher.urihttp://www.elsevier.com/wps/find/journaldescription.cws_home/129/description#description
dc.relation.ispartofstudentpublicationN
dc.relation.ispartofpagefrom3616
dc.relation.ispartofpageto3625
dc.relation.ispartofissue7
dc.relation.ispartofjournalBioorganic & Medicinal Chemistry
dc.relation.ispartofvolume16
dc.rights.retentionY
dc.subject.fieldofresearchMedicinal and Biomolecular Chemistry not elsewhere classified
dc.subject.fieldofresearchMedicinal and Biomolecular Chemistry
dc.subject.fieldofresearchOrganic Chemistry
dc.subject.fieldofresearchPharmacology and Pharmaceutical Sciences
dc.subject.fieldofresearchcode030499
dc.subject.fieldofresearchcode0304
dc.subject.fieldofresearchcode0305
dc.subject.fieldofresearchcode1115
dc.titleIn vitro permeability and metabolic stability of bile pigments and the effects of hydrophilic and lipophilic modification of biliverdin
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.date.issued2008
gro.hasfulltextNo Full Text
gro.griffith.authorBulmer, Andrew C.


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