Page last updated: 2024-11-10

mycolactone

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Description

mycolactone: toxin from Mycobacterium ulcerans required for virulence [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5282079
CHEBI ID31871
SCHEMBL ID1229472
MeSH IDM0300994

Synonyms (10)

Synonym
C12151 ,
mycolactone
[(6s,7s,9e,12r)-12-[(e,2s,6r,7r,9r)-7,9-dihydroxy-4,6-dimethyldec-4-en-2-yl]-7,9-dimethyl-2-oxo-1-oxacyclododec-9-en-6-yl] (2e,4e,6e,8e,10e,12s,13s,15s)-12,13,15-trihydroxy-4,6,10-trimethylhexadeca-2,4,6,8,10-pentaenoate
AC1NQZGK ,
222050-77-3
SCHEMBL1229472
CHEBI:31871
DTXSID10415207
[(6s,7s,9e,12r)-12-[(e,1s,5r,6r,8r)-6,8-dihydroxy-1,3,5-trimethyl-non-3-enyl]-7,9-dimethyl-2-oxo-1-oxacyclododec-9-en-6-yl] (2e,4e,6e,8e,10e,12s,13s,15s)-12,13,15-trihydroxy-4,6,10-trimethyl-hexadeca-2,4,6,8,10-pentaenoate
Q6947140

Research Excerpts

Overview

Mycolactones are a family of polyketide synthase products made by the human pathogen Mycobacterium ulcerans. They were recently identified as novel inhibitors of the host membrane translocation complex (Sec61) Mycolactone is the sole causative agent of the neglected tropical skin disease Buruli ulcer.

ExcerptReferenceRelevance
"Mycolactone is a light-sensitive and an amphiphilic toxin produced by Mycobacterium ulcerans."( Conditions for Handling and Optimal Storage of Mycolactone.
Kubicek-Sutherland, JZ; Mukundan, H; Swanson, BI, 2022
)
1.7
"Mycolactones are a family of polyketide synthase products made by the human pathogen Mycobacterium ulcerans that were recently identified as novel inhibitors of the host membrane translocation complex (Sec61). "( Mycolactone Purification from M. ulcerans Cultures and HPLC-Based Approaches for Mycolactone Quantification in Biological Samples.
Demangel, C; Guenin-Macé, L; Rifflet, A, 2022
)
3.61
"Mycolactone is a cytotoxic and immunosuppressive macrolide produced by Mycobacterium ulcerans and the sole causative agent of the neglected tropical skin disease Buruli ulcer. "( Can membrane composition traffic toxins? Mycolactone and preferential membrane interactions.
da Hora, GCA; Nguyen, JDM; Swanson, JMJ, 2022
)
2.43
"Mycolactone is a cytotoxic lipid metabolite produced by Mycobacterium ulcerans, the environmental pathogen responsible for Buruli ulcer, a neglected tropical disease. "( Behavioral interplay between mosquito and mycolactone produced by Mycobacterium ulcerans and bacterial gene expression induced by mosquito proximity.
Crippen, TL; Delclos, PJ; Dhungel, L; Jordan, HR; Kim, D; Tomberlin, JK, 2023
)
2.62
"Mycolactone is an exotoxin produced by "( Mycolactone A vs. B: Multiscale Simulations Reveal the Roles of Localization and Association in Isomer-Specific Toxicity.
da Hora, GCA; Nguyen, JDM; Swanson, JMJ, 2023
)
3.8
"Mycolactone is a plasmid-encoded, immunosuppressive, and cytotoxic toxin."( Mycolactone-producing Mycobacterium marinum infection in captive Hong Kong warty newts and pathological evidence of impaired host immune function.
Chang, HW; Chen, TY; Guo, JC; Jeng, CR; Li, WT; Liu, CH; Pang, VF; Wada, T; Wang, FI, 2017
)
2.62
"Mycolactone is a macrolide produced by the skin pathogen Mycobacterium ulcerans, with cytotoxic, analgesic and immunomodulatory properties. "( Mycolactone displays anti-inflammatory effects on the nervous system.
Ade, K; Boucher, Y; Demangel, C; Grimaldi, A; Guenin-Macé, L; Isaac, C; Limatola, C; Mauborgne, A; Pohl, M, 2017
)
3.34
"Mycolactone is a lipid-like endotoxin synthesized by an environmental human pathogen, Mycobacterium ulcerans, the causal agent of Buruli ulcer disease. "( The potent effect of mycolactone on lipid membranes.
Bénarouche, A; Canaan, S; Cavalier, JF; Dufourc, EJ; Géan, J; Girard-Egrot, AP; Maniti, O; Marion, E; Marsollier, L; Nitenberg, M, 2018
)
2.24
"Mycolactone is a bacteria-derived macrolide that blocks the biogenesis of a large array of secretory and integral transmembrane proteins (TMP) through potent inhibition of the Sec61 translocon. "( Proteomics Reveals Scope of Mycolactone-mediated Sec61 Blockade and Distinctive Stress Signature.
Demangel, C; Guenin-Macé, L; Impens, F; Morel, JD; Paatero, AO; Paavilainen, VO; Pietrosemoli, N; Van Haver, D; Wei, J; Yewdell, JW, 2018
)
2.22
"Mycolactone is a diffusible lipid secreted by the human pathogen Mycobacterium ulcerans, which induces the formation of open skin lesions referred to as Buruli ulcers. "( Mycolactone activation of Wiskott-Aldrich syndrome proteins underpins Buruli ulcer formation.
Bousso, P; Carlier, MF; Chrétien, F; Danckaert, A; Demangel, C; Guenin-Macé, L; Hong, H; Leadlay, PF; Mostowy, S; Romet-Lemonne, G; Ruf, MT; Thoulouze, MI; Veyron-Churlet, R; Zurzolo, C, 2013
)
3.28
"Mycolactones are a family of polyketide-derived macrolide exotoxins produced by Mycobacterium ulcerans, the causative agent of the chronic necrotizing skin disease Buruli ulcer. "( Structure-activity relationship studies on the macrolide exotoxin mycolactone of Mycobacterium ulcerans.
Altmann, KH; Bomio, C; Dangy, JP; Gersbach, P; Li, J; Pluschke, G; Scherr, N, 2013
)
2.07
"Mycolactone is a polyketide macrolide lipid-like secondary metabolite synthesized by Mycobacterium ulcerans, the causative agent of BU (Buruli ulcer), and is the only virulence factor for this pathogen identified to date. "( Pleiotropic molecular effects of the Mycobacterium ulcerans virulence factor mycolactone underlying the cell death and immunosuppression seen in Buruli ulcer.
Hall, B; Simmonds, R, 2014
)
2.07
"Mycolactone is a complex macrolide toxin produced by Mycobacterium ulcerans, the causative agent of skin lesions called Buruli ulcers. "( Synthetic variants of mycolactone bind and activate Wiskott-Aldrich syndrome proteins.
Blanchard, N; Casarotto, V; Chany, AC; Demangel, C; Guenin-Macé, L; Le Chevalier, F; Mayau, V; Tresse, C; Veyron-Churlet, R, 2014
)
2.16
"Mycolactone is a polyketide toxin secreted by the mycobacterium Mycobacterium ulcerans, responsible for the extensive hypoalgesic skin lesions characteristic of patients with Buruli ulcer. "( Mycolactone-mediated neurite degeneration and functional effects in cultured human and rat DRG neurons: Mechanisms underlying hypoalgesia in Buruli ulcer.
Anand, P; Anand, U; Bountra, C; Fox, M; Korchev, Y; MacQuillan, A; McCarthy, T; Quick, T; Sinisi, M, 2016
)
3.32
"Mycolactone is an immunosuppressive cytotoxin responsible for the clinical manifestation of Buruli ulcer in humans. "( Large sequence polymorphisms unveil the phylogenetic relationship of environmental and pathogenic mycobacteria related to Mycobacterium ulcerans.
Hauser, J; Käser, M; Pluschke, G; Small, P, 2009
)
1.8
"Mycolactone A/B is a lipophilic macrocyclic polyketide that is the primary virulence factor produced by Mycobacterium ulcerans, a human pathogen and the causative agent of Buruli ulcer. "( Mycolactone gene expression is controlled by strong SigA-like promoters with utility in studies of Mycobacterium ulcerans and buruli ulcer.
Azuolas, J; Davies, JK; Hong, H; Howden, BP; Jenkin, GA; Johnson, PD; Letournel, F; Marion, E; Marsollier, L; Pidot, SJ; Porter, JL; Seemann, T; Stinear, TP; Tobias, NJ; Wallace, JR; Zakir, T, 2009
)
3.24
"Mycolactone is a diffusible lipid toxin produced by Mycobacterium ulcerans, the causative agent of a necrotizing skin disease referred to as Buruli ulcer. "( Mycolactone suppresses T cell responsiveness by altering both early signaling and posttranslational events.
Bismuth, G; Boulkroun, S; Demangel, C; Di Bartolo, V; Guenin-Macé, L; Langsley, G; Merckx, A; Monot, M; Thoulouze, MI, 2010
)
3.25
"Mycolactone is a macrolide produced by Mycobacterium ulcerans with immunomodulatory properties. "( Mycolactone impairs T cell homing by suppressing microRNA control of L-selectin expression.
Asperti-Boursin, F; Bismuth, G; Caleechurn, L; Carrette, F; Demangel, C; Di Bartolo, V; Fontanet, A; Guenin-Macé, L; Le Bon, A, 2011
)
3.25
"Mycolactone is a macrolide secreted by Mycobacterium ulcerans. "( Uptake and cellular actions of mycolactone, a virulence determinant for Mycobacterium ulcerans.
Small, PL; Snyder, DS, 2003
)
2.05
"Mycolactone is a polyketide toxin produced by Mycobacterium ulcerans (Mu), the causative agent of the skin disease Buruli ulcer (BU). "( Selective suppression of dendritic cell functions by Mycobacterium ulcerans toxin mycolactone.
Albert, ML; Babon, A; Cole, ST; Coutanceau, E; Decalf, J; Demangel, C; Martino, A; Winter, N, 2007
)
2.01
"Mycolactone is a polyketide natural product secreted by Mycobacterium ulcerans, the organism responsible for the tropical skin disease Buruli ulcer. "( The unusual macrocycle forming thioesterase of mycolactone.
Barrows-Yano, T; Burkart, MD; Foley, TL; Meier, JL; Wike, CL, 2008
)
2.05

Effects

Mycolactone has pleiotropic effects on fundamental cellular processes (cell adhesion, cell death and inflammation)

ExcerptReferenceRelevance
"Mycolactone has previously been shown to bind to, and alter the structure of the major translocon subunit Sec61α, and change its interaction with ribosome nascent chain complexes."( Mycolactone enhances the Ca2+ leak from endoplasmic reticulum by trapping Sec61 translocons in a Ca2+ permeable state.
Bhadra, P; Cavalié, A; Dos Santos, S; Gamayun, I; Hall, BS; Helms, V; Neumann, C; Ogbechi, J; Pick, T; Simmonds, RE; Zimmermann, R, 2021
)
2.79
"Mycolactone has pleiotropic effects on fundamental cellular processes (cell adhesion, cell death and inflammation)."( The potent effect of mycolactone on lipid membranes.
Bénarouche, A; Canaan, S; Cavalier, JF; Dufourc, EJ; Géan, J; Girard-Egrot, AP; Maniti, O; Marion, E; Marsollier, L; Nitenberg, M, 2018
)
1.52
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
macrolideA macrocyclic lactone with a ring of twelve or more members derived from a polyketide.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (165)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (0.61)18.2507
2000's44 (26.67)29.6817
2010's86 (52.12)24.3611
2020's34 (20.61)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 34.40

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index34.40 (24.57)
Research Supply Index5.13 (2.92)
Research Growth Index5.87 (4.65)
Search Engine Demand Index43.69 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (34.40)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.60%)5.53%
Reviews22 (13.17%)6.00%
Case Studies1 (0.60%)4.05%
Observational0 (0.00%)0.25%
Other143 (85.63%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]