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One promising strategy involves designing novel compounds through targeted chemical modifications of existing antibiotics. Azithromycin (AZI), a widely used macrolide, has served as a versatile scaffold for developing numerous antibacterial candidates. However, the mechanistic consequences of such modifications remain largely unexplored. Here, we characterize the activity and mechanism of action of three AZI-benzoxaborole (AZI-BB) conjugates. We show that these compounds inhibit bacterial translation\n                      <jats:italic toggle=\"yes\">in vitro<\/jats:italic>\n                      and remain active against a model\n                      <jats:italic toggle=\"yes\">Escherichia coli<\/jats:italic>\n                      strain carrying an inducible\n                      <jats:italic toggle=\"yes\">ermCL-ermC<\/jats:italic>\n                      operon, which confers resistance to macrolide antibiotics. Unlike erythromycin, these derivatives, along with AZI itself, exhibit minimal induction of ErmC expression. Structural analysis reveals that the benzoxaborole moiety of AZI-BB2 forms additional interactions with nucleotides C2441 and C2586 of 23S rRNA, likely contributing to premature ribosome stalling at the\n                      <jats:italic toggle=\"yes\">ermCL<\/jats:italic>\n                      regulatory sequence and thereby preventing ErmC expression. Furthermore, high-throughput toeprinting analysis combined with deep sequencing (Toe-seq) demonstrates that AZI-BB2 exhibits reduced sequence specificity for canonical macrolide-sensitive stalling motifs. Altogether, these findings demonstrate that targeted chemical modification of AZI can reshape its context-specific interaction with the ribosome and attenuate the induction of macrolide resistance mechanisms.\n                    <\/jats:p>\n                  <\/jats:sec>","DOI":"10.1128\/aac.01539-25","type":"journal-article","created":{"date-parts":[[2026,3,24]],"date-time":"2026-03-24T14:29:16Z","timestamp":1774362556000},"update-policy":"https:\/\/doi.org\/10.1128\/asmj-crossmark-policy-page","source":"Crossref","is-referenced-by-count":1,"title":["Benzoxaborole-modified azithromycins inhibit translation without inducing\n                    <i>ermC<\/i>\n                    expression"],"prefix":"10.1128","volume":"70","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3852-653X","authenticated-orcid":true,"given":"Inna A.","family":"Volynkina","sequence":"first","affiliation":[{"id":[{"id":"https:\/\/ror.org\/010pmpe69","id-type":"ROR","asserted-by":"publisher"}],"name":"Department of Chemistry, Lomonosov Moscow State University","place":["Moscow, Russia"]},{"id":[{"id":"https:\/\/ror.org\/05shq4n12","id-type":"ROR","asserted-by":"publisher"}],"name":"Center for Molecular and Cellular Biology","place":["Moscow, Russia"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0000-0783-4321","authenticated-orcid":true,"given":"Michael O.","family":"Bortyazh","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/010pmpe69","id-type":"ROR","asserted-by":"publisher"}],"name":"Department of Chemistry, Lomonosov Moscow State University","place":["Moscow, Russia"]},{"id":[{"id":"https:\/\/ror.org\/010pmpe69","id-type":"ROR","asserted-by":"publisher"}],"name":"A.N. 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