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Transition state analogs of 5′-methylthioadenosine nucleosidase disrupt quorum sensing
Open accessAbstract
SUMMARY 5′-Methylthioadenosine nucleosidase (MTAN) is a bacterial enzyme involved in S-adenosylmethionine-related quorum sensing pathways that induce bacterial pathogenesis factors. Transition state analogues 5′-methylthio- (MT-), 5′-ethylthio- (EtT-) and 5′-butylthio- (BuT-) DADMe-ImmucillinAs are slow-onset, tight-binding inhibitors of Vibrio cholerae MTAN (VcMTAN), with dissociation constants of 73, 70, and 208 pM, respectively. Structural analysis of VcMTAN with BuT-DADMe-ImmucillinA reveals interactions contributing to the high affinity. In V. cholerae cells, these compounds are potent MTAN inhibitors with IC50 values of 27, 31, and 6 nM for MT-, EtT-, and BuT-DADMe-ImmucillinA, disrupting autoinducer production in a dose-dependent manner without affecting growth. MT- and BuT-DADMe-ImmucillinA also inhibit autoinducer-2 production in enterohemorrhagic Escherichia coli O157:H7 with IC50 values of 600, and 125 nM, respectively. BuT-DADMe-ImmucillinA inhibition of autoinducer-2 production in both strains persists for several generations, and causes reduction in biofilm formation. These results support MTAN’s role in quorum sensing, and its potential as target for bacterial anti-infective drug design.
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The biology and future prospects of antivirulence therapies
Cegelski, L., Marshall, G. R., Eldridge, G. R., & Hultgren, S. J. (2008) · Nature Reviews Microbiology · doi:10.1038/nrmicro1818 · Cited by 788
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Zhao, Y., Tian, Y., Cui, Y., Liu, W., Ma, W., & Jiang, X. (2010) · Journal of the American Chemical Society · doi:10.1021/ja1028843 · Cited by 592
Fleitas Martínez, O., Cardoso, M. H., Ribeiro, S. M., & Franco, O. L. (2019) · Frontiers in Cellular and Infection Microbiology · doi:10.3389/fcimb.2019.00074 · Cited by 304
Small molecule control of bacterial biofilms
Worthington, R. J., Richards, J. J., & Melander, C. (2012) · Organic & Biomolecular Chemistry · doi:10.1039/c2ob25835h · Cited by 299
Genetic control of bacterial biofilms
Wolska, K. I., Grudniak, A. M., Rudnicka, Z., & Markowska, K. (2016) · Journal of Applied Genetics · doi:10.1007/s13353-015-0309-2 · Cited by 154
Metadata
- Authors
- Gutierrez, J. A., Crowder, T., Rinaldo-Matthis, A., Ho, M.-C., Almo, S. C., & Schramm, V. L.
- Venue
- Nature Chemical Biology
- Published
- 2009-03-08
- Volume
- 5
- Issue
- 4
- Pages
- 251-257
- ISSN
- 1552-4450 (ISSN-L)
- 1552-4469
- OpenAlex
- W2060065181
- Cited by
- 164
- References
- 2
- FWCI
- 4.32
- Type
- journal article
- Language
- en
- Open access
- green
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