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is an important nosocomial pathogen that requires thoughtful consideration in the antibiotic prescription strategy due to its multidrug resistant phenotype. Tetracycline antibiotics have recently been re-administered as part of the combination antimicrobial regimens to treat infections caused by . We show that the TetA(G) efflux pump of AYE confers resistance to a variety of tetracyclines including the clinically important antibiotics doxycycline and minocycline, but not to tigecycline. Expression of gene is regulated by the TetR repressor of AYE (AbTetR). Thermal shift binding experiments revealed that AbTetR preferentially binds tetracyclines which carry a O-5H moiety in ring B, whereas tetracyclines with a 7-dimethylamino moiety in ring D are less well-recognized by AbTetR. Confoundingly, tigecycline binds to AbTetR even though it is not transported by TetA(G) efflux pump. Structural analysis of the minocycline-bound AbTetR-Gln116Ala variant suggested that the non-conserved Arg135 interacts with the ring D of minocycline by cation-π interaction, while the invariant Arg104 engages in H-bonding with the O-11H of minocycline. Interestingly, the Arg135Ala variant exhibited a binding preference for tetracyclines with an unmodified ring D. In contrast, the Arg104Ala variant preferred to bind tetracyclines which carry a O-6H moiety in ring C except for tigecycline. We propose that Arg104 and Arg135, which are embedded at the entrance of the AbTetR binding pocket, play important roles in the recognition of tetracyclines, and act as a barrier to prevent the release of tetracycline from its binding pocket upon AbTetR activation. The binding data and crystal structures obtained in this study might provide further insight for the development of new tetracycline antibiotics to evade the specific efflux resistance mechanism deployed by .
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http://dx.doi.org/10.3389/fmicb.2021.711158 | DOI Listing |
Chem Biodivers
December 2024
Banaras Hindu University, Chemistry, institute of science, 221005, Varanasi, INDIA.
1,2,3-triazole-based ring connected with pyridazine, triazine, methyl pyrazole, diphenyl pyrazole, and pthalimide moieties through propylene linker have been synthesized for antidiabetic evaluation via click chemistry. The antidiabetic evaluations have been done by molecular docking studies and in- vitro tests and against the DPP-4 enzyme. The molecular docking studies have revealed that compounds 22, 23, 29, and 30 showed hydrogen bond with the DPP-4 enzyme while in vitro tests has revealed the compound 30 has (IC50 values 12.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
December 2024
Shandong University, Chemistry and Chemical Engineering, Shanda South Road 27, 250100, Jinan, CHINA.
Catalytic transformation of carbene species constitutes a fundamental part in organic synthesis, and the research in this direction has been dominated by transition metals while organic catalysts are difficult to mimic such transition-metal-like reactivity. It would significantly advance carbene chemistry if organic catalysts enable achieving classical metal-carbene approaches otherwise unrealizable reactions. Herein, we report that chalcogen bonding catalysis can solve reactivity problem to achieve an elusive Buchner ring expansion of aryl ketones appending a cyclopropene moiety as carbene precursor.
View Article and Find Full Text PDFActa Crystallogr E Crystallogr Commun
October 2024
Department of Organic Chemistry University of Madras, Guindy Campus Chennai-600 025 Tamilnadu India.
Two new phenyl-sulfonyl-indole derivatives, namely, -{[3-bromo-1-(phenyl-sulfon-yl)-1-indol-2-yl]meth-yl}--(4-bromo-3-meth-oxy-phen-yl)benzene-sulfonamide, CHBrNOS, (), and ,-bis-{[3-bromo-1-(phenyl-sulfon-yl)-1-indol-2-yl]meth-yl}benzene-sulfonamide, CHBrNOS, (), reveal the impact of intra-molecular π-π inter-actions of the indole moieties as a factor not only governing the conformation of ,-bis-(1-indol-2-yl)meth-yl)amines, but also significantly influencing the crystal patterns. For , the crystal packing is dominated by C-H⋯π and π-π bonding, with a particular significance of mutual indole-indole inter-actions. In the case of , the mol-ecules adopt short intra-molecular π-π inter-actions between two nearly parallel indole ring systems [with the centroids of their pyrrole rings separated by 3.
View Article and Find Full Text PDFActa Crystallogr E Crystallogr Commun
October 2024
Institut für Organische Chemie Technische Universität Bergakademie, Freiberg, Leipziger Str 29 09599 Freiberg/Sachsen Germany.
In the crystal structure of the title compound, CHN, the tripodal mol-ecule exists in a conformation in which the substituents attached to the central arene ring are arranged in an alternating order above and below the ring plane. The three benzotriazolyl moieties are inclined at angles of 88.3 (1), 85.
View Article and Find Full Text PDFActa Crystallogr E Crystallogr Commun
October 2024
In the title mol-ecule, CHClNO, the 2-chloro-phenyl group is disordered to a small extent [occupancies 0.875 (2)/0.125 (2)].
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