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Cholesteroid nature of free mycolic acids from M. tuberculosis

Yolandy Benadie, Madrey Deysel, D. Gilbert R. Siko, Vanessa V. Roberts, Sandra Van Wyngaardt, Simon T. Thanyani, Gianna Sekanka, Annemieke M.C. Ten Bokum, Lynne A. Collett and Johan Grooten UGent, et al. (2008) CHEMISTRY AND PHYSICS OF LIPIDS. 152(2). p.95-103
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. We 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, we observed that AmB recognised both cholesterol and rnycolic acids. In addition, a specific attraction was observed between mycolic acid and cholesterol by the accumulation of cholesterol from liposomes ill Suspension onto immobilized mycolic acids containing liposomes, detected with a biosensor technique. Combined, these results suggest that mycolic acids call 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.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
journal title
CHEMISTRY AND PHYSICS OF LIPIDS
Chem. Phys. Lipids
volume
152
issue
2
pages
95 - 103
Web of Science type
Article
Web of Science id
000255809200005
JCR category
BIOPHYSICS
JCR impact factor
2.647 (2008)
JCR rank
31/70 (2008)
JCR quartile
2 (2008)
ISSN
0009-3084
DOI
10.1016/j.chemphyslip.2008.01.004
language
English
UGent publication?
yes
classification
A1
id
632556
handle
http://hdl.handle.net/1854/LU-632556
date created
2009-05-19 12:09:25
date last changed
2009-05-19 12:15:25
@article{632556,
  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. We 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, we observed that AmB recognised both cholesterol and rnycolic acids. In addition, a specific attraction was observed between mycolic acid and cholesterol by the accumulation of cholesterol from liposomes ill Suspension onto immobilized mycolic acids containing liposomes, detected with a biosensor technique. Combined, these results suggest that mycolic acids call 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.},
  author       = {Benadie, Yolandy and Deysel, Madrey and Siko, D. Gilbert R. and Roberts, Vanessa V. and Van Wyngaardt, Sandra and Thanyani, Simon T. and Sekanka, Gianna and Ten Bokum, Annemieke M.C. and Collett, Lynne A. and Grooten, Johan and Baird, Mark S. and Verschoor, Jan A.},
  issn         = {0009-3084},
  journal      = {CHEMISTRY AND PHYSICS OF LIPIDS},
  language     = {eng},
  number       = {2},
  pages        = {95--103},
  title        = {Cholesteroid nature of free mycolic acids from M. tuberculosis},
  url          = {http://dx.doi.org/10.1016/j.chemphyslip.2008.01.004},
  volume       = {152},
  year         = {2008},
}

Chicago
Benadie, Yolandy, Madrey Deysel, D. Gilbert R. Siko, Vanessa V. Roberts, Sandra Van Wyngaardt, Simon T. Thanyani, Gianna Sekanka, et al. 2008. “Cholesteroid Nature of Free Mycolic Acids from M. Tuberculosis.” Chemistry and Physics of Lipids 152 (2): 95–103.
APA
Benadie, Y., Deysel, M., Siko, D. G. R., Roberts, V. V., Van Wyngaardt, S., Thanyani, S. T., Sekanka, G., et al. (2008). Cholesteroid nature of free mycolic acids from M. tuberculosis. CHEMISTRY AND PHYSICS OF LIPIDS, 152(2), 95–103.
Vancouver
1.
Benadie Y, Deysel M, Siko DGR, Roberts VV, Van Wyngaardt S, Thanyani ST, et al. Cholesteroid nature of free mycolic acids from M. tuberculosis. CHEMISTRY AND PHYSICS OF LIPIDS. 2008;152(2):95–103.
MLA
Benadie, Yolandy, Madrey Deysel, D. Gilbert R. Siko, et al. “Cholesteroid Nature of Free Mycolic Acids from M. Tuberculosis.” CHEMISTRY AND PHYSICS OF LIPIDS 152.2 (2008): 95–103. Print.