Glycylcyclines bind to the high-affinity tetracycline ribosomal binding site and evade Tet(M)- and Tet(O)-mediated ribosomal protection
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N,N-dimethylglycylamido (DMG) derivatives of 6-demethyl-6-deoxytetracycline and doxycycline bind 5-fold more effectively than tetracycline to the tetracycline high-affinity binding site on the Escherichia coli 70S ribosome, which correlates with a 10-fold increase in potency for inhibition of E. coli cell-free translation. The potencies of DMG-doxycycline and DMG-6-demethyl-6-deoxytetracycline were unaffected by the ribosomal tetracycline resistance factors Tet(M) and Tet(O) in cell-free translation assays and whole-cell bioassays with a conditional Tet(M)-producing E. coli strain.
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The attached C9-glycyl side chain of tigecycline would prevent access of the residues of loop III of TetM, and this steric hindrance contributes, together with the increased affinity of tigecycline, to explaining how tigecycline overcomes TetM-mediated resistance whereas tetracycline cannot.
“In contrast, the attached C9-glycyl side chain of Tgc would prevent access of the residues of loop III of TetM (Fig. 3 E and F), leading us to suggest that this steric hindrance contributes, together with the increased affinity of Tgc (7,8,27), to explaining how Tgc overcomes TetM-mediated resistance whereas tetracycline cannot (8).”
From Structural basis for TetM-mediated tetracycline resistance (2012) · cites this paper as [7]
Third-generation tetracycline derivatives such as tigecycline display enhanced antimicrobial activity, overcoming efflux and ribosome protection mechanisms.
“The third generation of tetracycline derivatives, such as tigecycline (Tgc), display enhanced antimicrobial activity, overcoming efflux and ribosome protection mechanisms (6)(7)(8).”
From Structural basis for TetM-mediated tetracycline resistance (2012) · cites this paper as [7]
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- Authors
- Bergeron, J., Ammirati, M., Danley, D., James, L., Norcia, M., Retsema, J., Strick, C. A., Su, W. G., Sutcliffe, J., & Wondrack, L.
- Affiliations
- Pfizer (United States) (US)
- ORCID
- Ammirati, M
- Venue
- Antimicrobial Agents and Chemotherapy
- Publisher
- American Society for Microbiology
- Published
- 1996-09
- Volume
- 40
- Issue
- 9
- Pages
- 2226-2228
- ISSN
- 0066-4804 (ISSN-L)
- 1098-6596
- PMC
- PMC163507
- OpenAlex
- W2101570801
- Cited by
- 157
- References
- 24
- Citations by year
- 2026: 1 · 2025: 3 · 2024: 1 · 2023: 2 · 2022: 2 · 2021: 5 · 2020: 1 · 2019: 3 · 2018: 4 · 2017: 4 · 2016: 3 · 2015: 9 · 2014: 8 · 2013: 8 · 2012: 7
- FWCI
- 0.51
- Type
- journal article
- Language
- en
- Open access
- green
- europepmc.org
- Locations
- Antimicrobial Agents and Chemotherapy (publishedVersion)
- Europe PMC (PubMed Central) (publishedVersion)
- PubMed Central (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › RNA and protein synthesis mechanisms
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Medicine › Antibiotic Resistance in Bacteria
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Genetics › Bacterial Genetics and Biotechnology
- Keywords
- glycylcyclines, tetM, tetO, tetracycline resistance, Escherichia coli ribosome, antibiotic resistance
- MeSH terms
- Anti-Bacterial Agents, Biological Assay, Cell-Free System, Doxycycline, Escherichia coli, Glycylglycine, Peptide Biosynthesis, Ribosomes, Tetracycline Resistance
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