Inflammatory properties and adjuvant potential of synthetic glycolipids homologous to mycolate esters of the cell wall of Mycobacterium tuberculosis.

TIMA, Hermann Giresse; AL DULAYYMI, Juma’a Raheem; DENIS, Olivier; LEHEBEL, Pauline; BAOLS, Klarah Sherzad; MOHAMMED, Mohsin Omar; L’HOMME, Laurent; SAHB, Mohaned Mohammed; POTEMBERG, Georges; Legrand, Sylvie; LANG, Roland; BEYAERT, Rudi; PIETTE, Jacques; BAIRD, Mark Stephen; HUYGEN, Kris; ROMANO, Marta

doi:10.1159/000450955

Article (Scientific journals)

Inflammatory properties and adjuvant potential of synthetic glycolipids homologous to mycolate esters of the cell wall of Mycobacterium tuberculosis.

TIMA, Hermann Giresse; AL DULAYYMI, Juma’a Raheem; DENIS, Olivier et al.

2016 • In Journal of Innate Immunity

Peer Reviewed verified by ORBi

Permalink
https://hdl.handle.net/2268/204139

DOI
10.1159/000450955

PubMed
27855374

Files (1)Send to Details Statistics Bibliography Similar publications

Files

Full Text

Tima et al Glycolipids-final-September2016.pdf

Publisher postprint (407.28 kB)

Download

All documents in ORBi are protected by a user license.

Send to

RIS BibTex APA Chicago Permalink X Linkedin

Details

Disciplines :

Microbiology

Author, co-author :

TIMA, Hermann Giresse; Scientific Service Immunology, O.D. Communicable and Infectious Diseases, Scientific Institute of Public Health (WIV-ISP), B-1180 Brussels, Belgium

AL DULAYYMI, Juma’a Raheem

DENIS, Olivier

LEHEBEL, Pauline

BAOLS, Klarah Sherzad

MOHAMMED, Mohsin Omar

L’HOMME, Laurent

SAHB, Mohaned Mohammed

POTEMBERG, Georges

Legrand, Sylvie ; Université de Liège > GIGA-R : Virologie - Immunologie

More authors (6 more)

^✱ These authors have contributed equally to this work.

Language :

English

Title :

Inflammatory properties and adjuvant potential of synthetic glycolipids homologous to mycolate esters of the cell wall of Mycobacterium tuberculosis.

Publication date :

2016

Journal title :

Journal of Innate Immunity

ISSN :

1662-811X

eISSN :

1662-8128

Publisher :

Karger, Basel, Switzerland

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 08 December 2016

Statistics

Number of views

128 (15 by ULiège)

Number of downloads

275 (8 by ULiège)

More statistics

Scopus citations^®

Scopus citations^®
without self-citations

OpenCitations

OpenAlex citations

Bibliography

Minnikin DE, Kremer L, Dover LG, Besra GS: The methyl-branched fortifications of Mycobacterium tuberculosis . Chem Biol 2002; 9: 545-553.
Verschoor JA, Baird MS, Grooten J: Towards understanding the functional diversity of cell wall mycolic acids of Mycobacterium tuberculosis . Prog Lipid Res 2012; 51: 325-339.
Ojha AK, Baughn AD, Sambandan D, Hsu T, Trivelli X, Guerardel Y, et al: Growth of Mycobacterium tuberculosis biofilms containing free mycolic acids and harbouring drug-tolerant bacteria. Mol Microbiol 2008; 69: 164-174.
Dao DN, Sweeney K, Hsu T, Gurcha SS, Nascimento IP, Roshevsky D, et al: Mycolic acid modification by the mmaA4 gene of M. tuberculosis modulates IL-12 production. PLoS Pathog 2008; 4:e1000081.
Rao V, Fujiwara N, Porcelli SA, Glickman MS: Mycobacterium tuberculosis controls host innate immune activation through cyclopropane modification of a glycolipid effector molecule. J Exp Med 2005; 201: 535-543.
Behling CA, Perez RL, Kidd MR, Staton GW, Hunter RL: Induction of pulmonary granulomas, macrophage procoagulant activity, and tumor necrosis factor-alpha by trehalose glycolipids. Ann Clin Lab Sci 1993; 23: 256-266.
Perez RL, Roman J, Staton GW, Hunter RL: Extravascular coagulation and fibrinolysis in murine lung inflammation induced by the mycobacterial cord factor trehalose-6,6-dimycolate. Am J Respir Crit Care Med 1994; 149: 510-518.
Yarkoni E, Rapp HJ: Granuloma formation in lungs of mice after intravenous administration of emulsified trehalose-6,6-dimycolate (cord factor): reaction intensity depends on size distribution of the oil droplets. Infect Immun 1977; 18: 552-554.
Axelrod S, Oschkinat H, Enders J, Schlegel B, Brinkmann V, Kaufmann SHE, et al: Delay of phagosome maturation by a mycobacterial lipid is reversed by nitric oxide. Cell Microbiol 2008; 10: 1530-1545.
Gavin AL, Hoebe K, Duong B, Ota T, Martin C, Beutler B, et al: Adjuvant-enhanced antibody responses in the absence of toll-like receptor signaling. Science 2006; 314: 1936-1938.
Watanabe M, Aoyagi Y, Ridell M, Minnikin DE: Separation and characterization of individual mycolic acids in representative mycobacteria. Microbiology 2001; 147: 1825-1837.
Minnikin DE, Parlett JH, Magnusson M, Ridell M, Lind A: Mycolic acid patterns of representatives of Mycobacterium bovis BCG. J Gen Microbiol 1984; 130: 2733-2736.
Dubnau E, Chan J, Raynaud C, Mohan VP, Laneelle M a, Yu K, et al: Oxygenated mycolic acids are necessary for virulence of Mycobacterium tuberculosis in mice. Mol Microbiol 2000; 36: 630-637.
Barkan D, Hedhli D, Yan H-G, Huygen K, Glickman MS: Mycobacterium tuberculosis lacking all mycolic acid cyclopropanation is viable but highly attenuated and hyperinflammatory in mice. Infect Immun 2012; 80: 1958-1968.
Ueda S, Fujiwara N, Naka T, Sakaguchi I, Ozeki Y, Yano I, et al: Structure-activity relationship of mycoloyl glycolipids derived from Rhodococcus sp. 4306. Microb Pathog 2001; 30: 91-99.
Nishizawa M, Yamamoto H, Imagawa H, Barbier-Chassefiere V, Petit E, Azuma I, et al: Efficient syntheses of a series of trehalose dimycolate (TDM)/trehalose dicorynomycolate (TDCM) analogues and their interleukin-6 level enhancement activity in mice sera. J Org Chem 2007; 72: 1627-1633.
Moody DB, Reinhold BB, Guy MR, Beckman EM, Frederique DE, Furlong ST, et al: Structural requirements for glycolipid antigen recognition by CD1b-restricted T cells. Science 1997; 278: 283-286.
Ishikawa E, Ishikawa T, Morita YS, Toyonaga K, Yamada H, Takeuchi O, et al: Direct recognition of the mycobacterial glycolipid, trehalose dimycolate, by C-type lectin Mincle. J Exp Med 2009; 206: 2879-2888.
van der Peet PL, Gunawan C, Torigoe S, Yamasaki S, Williams SJ: Corynomycolic acidcontaining glycolipids signal through the pattern recognition receptor Mincle. Chem Commun 2015; 51: 5100-5103.
Schoenen H, Bodendorfer B, Hitchens K, Manzanero S, Werninghaus K, Nimmerjahn F, et al: Cutting edge: Mincle is essential for recognition and adjuvanticity of the mycobacterial cord factor and its synthetic analog trehalose-dibehenate. J Immunol 2010; 184: 2756-2760.
Stocker BL, Khan AA, Chee SH, Kamena F, Timmer MSM: On one leg: trehalose monoesters activate macrophages in a Mincle-dependant manner. Chembiochem 2014; 15: 382-388.
Miyauchi M: Arabino-mycolates derived from cell-wall skeleton of Mycobacterium bovis BCG as a prominent structure for recognition by host immunity. Drug Discov Ther 2011; 5: 130-135.
Schweneker K, Gorka O, Schweneker M, Poeck H, Tschopp J, Peschel C, et al: The mycobacterial cord factor adjuvant analogue trehalose-6,6-dibehenate (TDB) activates the Nlrp3 inflammasome. Immunobiology 2013; 218: 664-673.
Desel C, Werninghaus K, Ritter M, Jozefowski K, Wenzel J, Russkamp N, et al: The Mincle-activating adjuvant TDB induces MyD88-dependent Th1 and Th17 responses through IL-1R signaling. PLoS One 2013; 8:e53531.
Mohammed M: Arabinose Mycolates from Synthetic Mycolic Acids; PhD thesis, Bangor University, Bangor, 2015.
Sahb MM, Dulayymi JR Al, Baird MS: Glucose monomycolates based on single synthetic mycolic acids. Chem Phys Lipids 2015; 190: 9-14.
Al Dulayymi JR, Baird MS, Maza-Iglesias M, Hameed RT, Baols KS, Muzael M, et al: Synthetic trehalose di-and mono-esters of -, methoxy-and keto-mycolic acids. Tetrahedron 2014; 70: 9836-9852.
Al Dulayymi JR, Baird MS, Maza-Iglesias M, Vander Beken S, Grooten J: The first unique synthetic mycobacterial cord factors. Tetrahedron Lett 2009; 50: 3702-3705.
Ruland J, Duncan GS, Wakeham A, Mak TW: Differential requirement for Malt1 in T and B cell antigen receptor signaling. Immunity 2003; 19: 749-758.
Taher SG, Al Dulayymi JR, Baird MS: Synthetic trehalose esters of cis-alkene and diene '-mycolic acids of Mycobacteria . Chem Phys Lipids 2015; 189: 28-38.
Baols KS: Synthesis of mixed cord factors and related compounds; PhD thesis, Bangor University, Bangor, 2014.
Inaba K, Inaba M, Romani N, Aya H, Deguchi M, Ikehara S, Muramatsu S, Steinman RM: Generation of large numbers of dendritic cells from mouse bone marrow cultures supplemented with granulocyte/macrophage colony-stimulating factor. J Exp Med 1992; 176: 1693-1702.
Yarkoni E, Rapp HJ: Granuloma formation in lungs of mice after intravenous administration of emulsified trehalose-6,6-dimycolate (cord factor): reaction intensity depends on size distribution of the oil droplets. Infect Immun 1977; 18: 552-554.
Miyake Y, Toyonaga K, Mori D, Kakuta S, Hoshino Y, Oyamada A, et al: C-type Lectin MCL is an FcR-coupled receptor that mediates the adjuvanticity of mycobacterial cord factor. Immunity 2013; 38: 1050-1062.
Schroder K, Tschopp J: The inflammasomes. Cell 2010; 140: 821-832.
Rao V, Gao F, Chen B, Jacobs WR, Glickman MS: Trans-cyclopropanation of mycolic acids on trehalose dimycolate suppresses Mycobacterium tuberculosis-induced inflammation and virulence. J Clin Invest 2006; 116: 1660-1667.
Ostrop J, Jozefowski K, Zimmermann S, Hofmann K, Strasser E, Lepenies B, et al: Contribution of MINCLE-SYK signaling to activation of primary human APCs by mycobacterial cord factor and the novel adjuvant TDB. J Immunol 2015; 195: 2417-2428.
Matsunaga I, Naka T, Talekar RS, McConnell MJ, Katoh K, Nakao H, et al: Mycolyltransferase-mediated glycolipid exchange in Mycobacteria. J Biol Chem 2008; 283: 28835-28841.
Shenderov K, Barber DL, Mayer-Barber KD, Gurcha SS, Jankovic D, Feng CG, et al: Cord factor and peptidoglycan recapitulate the Th17-promoting adjuvant activity of mycobacteria through Mincle/CARD9 signaling and the inflammasome. J Immunol 2013; 190: 5722-5730.
Huber A, Kallerup RS, Korsholm KS, Franzyk H, Lepenies B, Christensen D, et al: Trehalose diester glycolipids are superior to the monoesters in binding to Mincle, activation of macrophages in vitro and adjuvant activity in vivo. Innate Immun 2016;22:405-418.
Hunter RL, Armitige L, Jagannath C, Actor JK: TB Research at UT-Houston-a review of cord factor: new approaches to drugs, vaccines and the pathogenesis of tuberculosis. Tuberculosis 2009; 89: 1-20.
Fujita Y, Okamoto Y, Uenishi Y, Sunagawa M, Uchiyama T, Yano I: Molecular and supramolecular structure related differences in toxicity and granulomatogenic activity of mycobacterial cord factor in mice. Microb Pathog 2007;43:10-21.
Felio K, Nguyen H, Dascher CC, Choi H, Li S, Zimmer MI, et al: CD1-restricted adaptive immune responses to Mycobacteria in human group 1 CD1 transgenic mice. J Exp Med 2009; 206: 2497-2509.