Mycolactone Purification from M. ulcerans Cultures and HPLC-Based Approaches for Mycolactone Quantification in Biological Samples.
Folch’s extraction
LC-MS/MS
Mycobacterium ulcerans
Mycolactone
TLC
Journal
Methods in molecular biology (Clifton, N.J.)
ISSN: 1940-6029
Titre abrégé: Methods Mol Biol
Pays: United States
ID NLM: 9214969
Informations de publication
Date de publication:
2022
2022
Historique:
entrez:
13
10
2021
pubmed:
14
10
2021
medline:
8
1
2022
Statut:
ppublish
Résumé
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). Here, we provide protocols for the purification of mycolactones from bacterial cultures, and for their quantitative assessment in biological samples.
Identifiants
pubmed: 34643908
doi: 10.1007/978-1-0716-1779-3_13
doi:
Substances chimiques
Macrolides
0
mycolactone
0
Polyketide Synthases
79956-01-7
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
117-130Informations de copyright
© 2022. The Author(s), under exclusive license to Springer Science+Business Media, LLC, part of Springer Nature.
Références
George KM, Chatterjee D, Gunawardana G et al (1999) Mycolactone: a polyketide toxin from mycobacterium ulcerans required for virulence. Science 283:854–857
doi: 10.1126/science.283.5403.854
Guenin-Macé L, Ruf M-T, Pluschke G, Demangel C (2019) Mycolactone: more than just a cytotoxin. In: Pluschke G, Röltgen K (eds) Buruli ulcer: mycobacterium ulcerans disease. Springer International Publishing, Cham, pp 117–134
doi: 10.1007/978-3-030-11114-4_7
Gehringer M, Altmann K-H (2017) The chemistry and biology of mycolactones. Beilstein J Org Chem 13:1596–1660. https://doi.org/10.3762/bjoc.13.159
doi: 10.3762/bjoc.13.159
pubmed: 28904608
pmcid: 5564285
Hong H, Demangel C, Pidot SJ et al (2008) Mycolactones: immunosuppressive and cytotoxic polyketides produced by aquatic mycobacteria. Nat Prod Rep 25:447–454. https://doi.org/10.1039/b803101k
doi: 10.1039/b803101k
pubmed: 18497894
pmcid: 2730631
Doig KD, Holt KE, Fyfe JAM et al (2012) On the origin of mycobacterium ulcerans, the causative agent of Buruli ulcer. BMC Genomics 13:258. https://doi.org/10.1186/1471-2164-13-258
doi: 10.1186/1471-2164-13-258
pubmed: 22712622
pmcid: 3434033
Scherr N, Gersbach P, Dangy JP et al (2013) Structure-activity relationship studies on the macrolide exotoxin mycolactone of mycobacterium ulcerans. PLoS Negl Trop Dis 7:e2143. https://doi.org/10.1371/journal.pntd.0002143
doi: 10.1371/journal.pntd.0002143
pubmed: 23556027
pmcid: 3610637
Mve-Obiang A, Lee RE, Portaels F, Small PLC (2003) Heterogeneity of mycolactones produced by clinical isolates of mycobacterium ulcerans: implications for virulence. Infect Immun 71:774–783. https://doi.org/10.1128/iai.71.2.774-783.2003
doi: 10.1128/iai.71.2.774-783.2003
pubmed: 12540557
pmcid: 145382
Hong H, Stinear T, Porter J et al (2007) A novel mycolactone toxin obtained by biosynthetic engineering. Chembiochem 8:2043–2047. https://doi.org/10.1002/cbic.200700411
doi: 10.1002/cbic.200700411
pubmed: 17907121
pmcid: 2699038
Baron L, Paatero AO, Morel JD et al (2016) Mycolactone subverts immunity by selectively blocking the Sec61 translocon. J Exp Med 213:2885–2896. https://doi.org/10.1084/jem.20160662
doi: 10.1084/jem.20160662
pubmed: 27821549
pmcid: 5154940
Demangel C, High S (2018) Sec61 blockade by mycolactone: a central mechanism in Buruli ulcer disease. Biol Cell 110:237–248. https://doi.org/10.1111/boc.201800030
doi: 10.1111/boc.201800030
pubmed: 30055020
Sarfo FS, Le Chevalier F, Aka N et al (2011) Mycolactone diffuses into the peripheral blood of Buruli ulcer patients--implications for diagnosis and disease monitoring. PLoS Negl Trop Dis 5:e1237. https://doi.org/10.1371/journal.pntd.0001237
doi: 10.1371/journal.pntd.0001237
pubmed: 21811642
pmcid: 3139662
Sarfo FS, Phillips RO, Zhang J et al (2014) Kinetics of mycolactone in human subcutaneous tissue during antibiotic therapy for mycobacterium ulcerans disease. BMC Infect Dis 14:202. https://doi.org/10.1186/1471-2334-14-202
doi: 10.1186/1471-2334-14-202
pubmed: 24731247
pmcid: 4021496
Folch J, Lees M, Sloane Stanley GH (1957) A simple method for the isolation and purification of total lipides from animal tissues. J Biol Chem 226:497–509
doi: 10.1016/S0021-9258(18)64849-5
Saint-Auret S, Abdelkafi H, Le Nouen D et al (2017) Modular total syntheses of mycolactone A/B and its [2H]-isotopologue. Org Biomol Chem 15:7518–7522. https://doi.org/10.1039/c7ob01943b
doi: 10.1039/c7ob01943b
pubmed: 28871293
Marion E, Prado S, Cano C et al (2012) Photodegradation of the mycobacterium ulcerans toxin, mycolactones: considerations for handling and storage. PLoS One 7:e33600. https://doi.org/10.1371/journal.pone.0033600
doi: 10.1371/journal.pone.0033600
pubmed: 22514607
pmcid: 3326021
Spangenberg T, Kishi Y (2010) Highly sensitive, operationally simple, cost/time effective detection of the mycolactones from the human pathogen mycobacterium ulcerans. Chem Commun (Camb) 46:1410–1412. https://doi.org/10.1039/b924896j
doi: 10.1039/b924896j
Kubicek-Sutherland JZ, Vu DM, Anderson AS et al (2019) Understanding the significance of biochemistry in the storage, handling, purification, and sampling of amphiphilic mycolactone. Toxins (Basel) 11:202. https://doi.org/10.3390/toxins11040202
doi: 10.3390/toxins11040202
Hong H, Gates PJ, Staunton J et al (2003) Identification using LC-MSn of co-metabolites in the biosynthesis of the polyketide toxin mycolactone by a clinical isolate of mycobacterium ulcerans. Chem Commun (Camb):2822–2823. https://doi.org/10.1039/b308163j