The first unique synthetic mycobacterial cord factors

Dulayymi, Juma’a R. Al; Baird, Mark S.; Maza-Iglesias, Maximiliano; Beken, Seppe Vander; Grooten, Johan

doi:10.1016/j.tetlet.2009.03.213

Cited by 30 publications

(32 citation statements)

References 38 publications

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“…Stocks of synthetic glycolipids (synthetized at Bangor University [25][26][27][28]30,31], TDB (Invivogen) and natural TDM from Mtb (Adipogen) were solubilised in chloroform-methanol solution (9:1) at 5mg/mL. The different glycolipids were then dissolved in isopropanol and coated on flat bottomed culture plates (Greiner).…”

Section: Preparation Of Glycolipid Coated Platesmentioning

confidence: 99%

“…To study the influence of the class of mycolates and the number of mycolate chains on the inflammatory potential of trehalose mycolate esters, 17 trehalose dimycolates and 13 trehalose monomycolates were synthetized (Table1, TDM and TMM columns) [25][26][27][28]30,31]. we observed that the number of mycolate chains bound to trehalose influenced the level of TNF-α and IL-6 produced.…”

Section: Synthetic Trehalose Di-and Mono-mycolates Are Inflammatorymentioning

confidence: 99%

“…To address the relationship between the structure and the inflammatory power of mycolate esters and the signalling pathways involved, we have assayed in this study thirty-eight single synthetic mycolate ester isomers of high purity and known stereochemistry [25][26][27][28]. The mycolate esters tested here vary in terms of their carbohydrate moiety (trehalose, glucose or arabinose) and in terms of the number, nature and class of mycolic acids bound to it.…”

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confidence: 99%

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Inflammatory Properties and Adjuvant Potential of Synthetic Glycolipids Homologous to Mycolate Esters of the Cell Wall of Mycobacterium tuberculosis

Tima

Dulayymi²,

Denis³

et al. 2016

J Innate Immun

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Inflammatory properties and adjuvant potential of synthetic glycolipids homologous to mycolate esters of the cell wall of Mycobacterium tuberculosis.Hermann Giresse TIMA (1), Juma'a Raheem AL DULAYYMI (2), Olivier DENIS (1), Pauline LEHEBEL (1), Klarah Sherzad BAOLS (2), Mohsin Omar MOHAMMED (2), Laurent L'HOMME (3), Mohaned Mohammed SAHB (2), Georges POTEMBERG (1), Sylvie LEGRAND (3), Roland LANG (4), Rudi BEYAERT (5), Jacques PIETTE (3), MarkStephen BAIRD (2)#, Kris HUYGEN (1)#, Marta ROMANO (1)*#.

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Section: Preparation Of Glycolipid Coated Platesmentioning

confidence: 99%

Section: Synthetic Trehalose Di-and Mono-mycolates Are Inflammatorymentioning

confidence: 99%

mentioning

confidence: 99%

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Inflammatory Properties and Adjuvant Potential of Synthetic Glycolipids Homologous to Mycolate Esters of the Cell Wall of Mycobacterium tuberculosis

Tima

Dulayymi²,

Denis³

et al. 2016

J Innate Immun

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“…TMM from M.tuberculosis showed a distinctive pattern with abundant odd-carbon- Since the physico-chemical properties and antigenic structure of the TDM affect the host immune responses, the detailed profiling of intact TDM represents a significant advance [53,54]. TDM and TMM prepared from single synthetic alpha-and methoxy-mycolic acids have been reported [55].…”

Section: Trehalose Mycolatesmentioning

confidence: 99%

Towards understanding the functional diversity of cell wall mycolic acids of Mycobacterium tuberculosis

Verschoor

Baird

Grooten

2012

Progress in Lipid Research

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Mycolic acids constitute the waxy layer of the outer cell wall of Mycobacterium spp and a few other genera. They are diverse in structure, providing a unique chromatographic foot-print for almost each of the more than seventy Mycobacterium species. Although mainly esterified to cell wall arabinogalactan, trehalose or glucose, some free mycolic acid is secreted during in vitro growth of M. tuberculosis. In M. tuberculosis, alpha-, keto-and methoxy-mycolic acids are the main classes, each differing in their ability to attract neutrophils, induce foamy macrophages or adopt an antigenic structure for antibody recognition. Of interest is their particular relationship to cholesterol, discovered by their ability to attract cholesterol, to bind Amphotericin B or to be recognised by monoclonal antibodies that cross-react with cholesterol. The structural elements that determine this diverse functionality include the carboxylic acid in the mycolic motif, as well as the nature and stereochemistry of the two functional groups in the merochain. The functional diversity of mycolic acid classes implies that much information may be contained in the selective expression and secretion of mycolic acids to establish tuberculosis after infection of the host. Their cholesteroid nature may relate to how they utilize host cholesterol for their persistent survival.

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“…Although there are several strategies for the synthesis of medium-to long-chain TMEs, [29,30] there are only a few routes for the generation of very-long-chain TMEs (> C 20 ), most notably the preparation of trehalose monocorynomycolates (TMCMs) [31] and the synthesis of trehalose monomycolate en route to TDM. [32] There is a remarkable difference in reactivity-attributable to poor solubility-between long and verylong chain fatty acids, and our experience with very-long-chain TDEs [28] thus prompted us to explore the use of TMS-protected trehalose en route to the preparation of lipophilic TMEs. To this end, a,a'-trehalose (4, Scheme 2) was treated with N,Obis(trimethylsilyl)acetamide (BSA), catalytic TBAF and K 2 CO 3 to generate TMS-protected diol 5 in excellent yield.…”

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confidence: 99%

On One Leg: Trehalose Monoesters Activate Macrophages in a Mincle‐Dependent Manner

et al. 2014

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The C22 and C26 trehalose monoesters, each containing a single acyl chain, were synthesised in good overall yields and found to activate macrophages in a Mincle-dependent manner. The activities of the monoesters paralleled those of their diester counterparts, and both mono- and diesters could activate the immune response in the absence of priming. This is the first time that trehalose monoesters have been found to activate macrophages, and these studies thus provide an important framework for the rational design of other Mincle agonists.

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The first unique synthetic mycobacterial cord factors

Cited by 30 publications

References 38 publications

Inflammatory Properties and Adjuvant Potential of Synthetic Glycolipids Homologous to Mycolate Esters of the Cell Wall of <b><i>Mycobacterium tuberculosis</i></b>

Inflammatory Properties and Adjuvant Potential of Synthetic Glycolipids Homologous to Mycolate Esters of the Cell Wall of <b><i>Mycobacterium tuberculosis</i></b>

Towards understanding the functional diversity of cell wall mycolic acids of Mycobacterium tuberculosis

On One Leg: Trehalose Monoesters Activate Macrophages in a Mincle‐Dependent Manner

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