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Please use this identifier to cite or link to this item: http://hdl.handle.net/10204/4954

Title: Cholesteroid nature of free mycolic acids from m. tuberculosis
Authors: Benadie, Y
Deysel, M
Siko, DGR
Roberts, VV
Van Wyngaardt, S
Thanyani, ST
Sekanka, G
Ten Bokum, AMC
Collett, LA
Grooten, J
Baird, MS
Verschoor, JA
Keywords: Mycolic acids
Lipid conformation
Amphotericin B
Resonant mirror biosensor
Issue Date: 2008
Publisher: Elsevier
Citation: Benadie, Y, Deysel, M, Siko, DGR et al. 2008. Cholesteroid nature of free mycolic acids from M. tuberculosis. Chemistry and physics of lipids, vol. 152(2), pp 95–103
Series/Report no.: Workflow request;5318
Abstract: Mycolic acids (MAs) are a major component of the cell walls of Mycobacterium tuberculosis and related organisms. These alpha-alkyl beta-hydroxy long fatty acids have been the subject of numerous studies for their immunological properties. The authors previously reported that an interaction between cholesterol and mycolic acids could be responsible for the low accuracy in the serodiagnosis of TB when using free mycolic acid in an ELISA assay. The aim of this work was to investigate if this interaction could be due to a similarity in the structural properties between mycolic acids and cholesterol. The investigation revealed that patient sera cross-reacted with mycolic acids and cholesterol in an ELISA experiment suggesting that both molecules may present related functionality in a similar structural orientation. This relation was further supported by the interaction of mycolic acids with Amphotericin B (AmB), a known binding agent to ergosterol and cholesterol. Using a resonant mirror biosensor, they observed that AmB recognised both cholesterol and mycolic acids. In addition, a specific attraction was observed between mycolic acid and cholesterol by the accumulation of cholesterol from liposomes in suspension onto immobilized mycolic acids containing liposomes, detected with a biosensor technique. Combined, these results suggest that mycolic acids can assume a three-dimensional conformation similar to a sterol. This requires that mycolic acid exposes its hydroxyl group and assumes rigidity in its chain structure to generate a hydrophobic surface topology matching that of cholesterol. A particular folded conformation would be required for this, of which a few different types have already been proven to exist in monolayers of mycolic acids.
Description: Copyright: 2008 Elsevier. This is the Pre print version of the work. The definitive version is published in the Chemistry and Physics of Lipids, vol.152(2), pp 95-103
URI: http://www.sciencedirect.com/science?_ob=MImg&_imagekey=B6T2N-4RSJDXN-1-J&_cdi=4923&_user=958262&_pii=S0009308408000182&_origin=gateway&_coverDate=04%2F30%2F2008&_sk=998479997&view=c&wchp=dGLbVlW-zSkWA&md5=2f9d75af9f113f2d05c8ebbd3b1a6f60&ie=/sdarticle.pdf
ISSN: 0009-3084
Appears in Collections:Polymers and composites
Polymers and bioceramics
General science, engineering & technology

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