Synthetic Studies toward <i>Mycobacterium tuberculosis</i> Sulfolipid-I

Leigh, Clifton D.; Bertozzi, Carolyn R.

doi:10.1021/jo702032c

Cited by 57 publications

(47 citation statements)

References 41 publications

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“…2,3,6,6Ј-Tetraacyltrehalose 2Ј-sulfate (sulfolipid I [SL-I]), a compound found abundantly in the M. tuberculosis cell wall, may affect the human immune system and play a role in the pathogenesis of TB (51). SL-I yielded a sensitivity of 80% (95% CI, 56 to 93) and a specificity of 59% (95% CI, 8 to 96) (43,44).…”

Section: Resultsmentioning

confidence: 99%

Performance of Purified Antigens for Serodiagnosis of Pulmonary Tuberculosis: a Meta-Analysis

Steingart

Dendukuri

Henry

et al. 2009

Clin Vaccine Immunol

170

137

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The failure to diagnose tuberculosis (TB) accurately and rapidly is a key challenge in curbing the epidemic (45,88,116). Sputum microscopy, currently the sole diagnostic test in most areas where TB is endemic, has several limitations; in particular, the sensitivity compared with that of culture is variable (80,97,104,116), multiple patient visits are required (56,93,114), considerable technical training is necessary, and the procedure is labor-intensive (45, 65). Antibody detection tests (serological tests) are used for the diagnosis of many infectious diseases and could potentially improve the means of diagnosis of TB. These tests measure the presence of specific antibodies (most often immunoglobulin G [IgG]) directed against immunodominant antigens of the pathogen in question. Compared with microscopy, antibody detection methods may enable the rapid diagnosis of TB, as these tests have the advantages of speed (results can be available within hours), technological simplicity, and minimal training requirements. In addition, these tests can be adapted to point-of-care formats that can be implemented at lower levels of health services in low-and middle-income countries (21,22,57,65).Efforts to develop antibody detection tests for the diagnosis of TB have been under way for decades, and the performance of these tests has been well described (13,17,22,32,40,47,48,52,60,64,100,107). Several systematic reviews of these tests have been published (discussed below) (28,94,95).First-generation antibody detection tests were based on crude mixtures of constituents and products of Mycobacterium tuberculosis, for example, culture filtrate proteins and purified protein derivative, the preparation used in the tuberculin skin test. Several of these early tests had low specificities, as the tests contained antigens shared among different bacterial species (1,22,48,57). During the past two decades, an increased understanding of humoral immune responses to M. tuberculosis and the new tools of

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Section: Resultsmentioning

confidence: 99%

Performance of Purified Antigens for Serodiagnosis of Pulmonary Tuberculosis: a Meta-Analysis

Steingart

Dendukuri

Henry

et al. 2009

Clin Vaccine Immunol

170

137

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“…This method, which also required specialized sugar building blocks, was used to synthesize complex sulfolipid-1 analogues from M. tuberculosis for immunological SAR studies. 55,56 For a comprehensive review of chemical 1,1-α,α-glycosylation methods, readers are referred to a recent review article by Chaube and Kulkarni. 10 …”

Section: Approaches To Trehalose Analogue Synthesismentioning

confidence: 99%

Tailoring trehalose for biomedical and biotechnological applications

O'Neill

Piligian

Olson

et al. 2017

Pure and Applied Chemistry

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Trehalose is a non-reducing sugar whose ability to stabilize biomolecules has brought about its widespread use in biological preservation applications. Trehalose is also an essential metabolite in a number of pathogens, most significantly the global pathogen Mycobacterium tuberculosis, though it is absent in humans and other mammals. Recently, there has been a surge of interest in modifying the structure of trehalose to generate analogues that have applications in biomedical research and biotechnology. Non-degradable trehalose analogues could have a number of advantages as bioprotectants and food additives. Trehalose-based imaging probes and inhibitors are already useful as research tools and may have future value in the diagnosis and treatment of tuberculosis, among other uses. Underlying the advancements made in these areas are novel synthetic methods that facilitate access to and evaluation of trehalose analogues. In this review, we focus on both aspects of the development of this class of molecules. First, we consider the chemical and chemoenzymatic methods that have been used to prepare trehalose analogues and discuss their prospects for synthesis on commercially relevant scales. Second, we describe ongoing efforts to develop and deploy detectable trehalose analogues, trehalose-based inhibitors, and non-digestible trehalose analogues. The current and potential future uses of these compounds are discussed, with an emphasis on their roles in understanding and combatting mycobacterial infection.

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“…SL-1 can be acylated by 2 to 4 very long (up to C 64 ) saturated and unsaturated, highly branched fatty acids. Sulfate derivatives are rare in natural substances, and some of the acyl chains of SL-1 are also uncommon, since they are mainly highly branched in their carboxyl end (Goren & Mor, 1990;Leigh & Bertozzi, 2008). The SLs have attracted much interest since it was shown that, like TDM, they seem to inhibit phagosome-lysosome fusion in macrophages (Goren et al, 1976), and are cytotoxic (Kato & Goren, 1974a, 1974b.…”

Section: The Peripheral Lipid Layer In the M Tuberculosis Cell Wallmentioning

confidence: 99%

Broadening Our View About the Role of Mycobacterium tuberculosis Cell Envelope Components During Infection: A Battle for Survival

Torrelles¹

2012

Understanding Tuberculosis - Analyzing the Origin of Mycobacterium Tuberculosis Pathogenicity

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Synthetic Studies toward Mycobacterium tuberculosis Sulfolipid-I

Cited by 57 publications

References 41 publications

Performance of Purified Antigens for Serodiagnosis of Pulmonary Tuberculosis: a Meta-Analysis

Performance of Purified Antigens for Serodiagnosis of Pulmonary Tuberculosis: a Meta-Analysis

Tailoring trehalose for biomedical and biotechnological applications

Broadening Our View About the Role of Mycobacterium tuberculosis Cell Envelope Components During Infection: A Battle for Survival

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