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Antibacterial implant coatings are an important approach to reduce or prevent bacterial infections at the implant. Given the oral cavity's complex microbiome and the importance of some commensal bacteria, it is crucial to develop antibacterial implant coatings that release the active ingredient only when needed. In this work, an enzyme\u2010triggered drug delivery coating based on chitosan with ciprofloxacin as antibiotic was synthesized. The ciprofloxacin is covalently bound via a self\u2010immolative linker with an enzyme\u2010labile group. The linker\u2010drug conjugate was bound to modified chitosan through a Diels\u2013Alder click reaction. A stable drug\u2010delivering coating was assembled on titanium by alternating cationic chitosan with the drug with anionic alginate using layer\u2010by\u2010layer dip\u2010coating. Ellipsometry was used to characterize the coating and demonstrating its stability. The function of the enzyme\u2010labile self\u2010immolative linker was clearly demonstrated by release experiments and detection of genuine ciprofloxacin using UHPLC\/HRAM\u2010MS and MS\/MS. Furthermore, its biocompatibility was confirmed. After enzymatic activation, the coating exhibited antibacterial activity against an\n                    <jats:italic>A. naeslundii<\/jats:italic>\n                    biofilm. This provides proof of principle for this enzyme\u2010responsive approach to drug delivery.\n                  <\/jats:p>","DOI":"10.1002\/chem.202501800","type":"journal-article","created":{"date-parts":[[2026,2,15]],"date-time":"2026-02-15T08:29:00Z","timestamp":1771144140000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Synthesis of an Enzyme\u2010Triggered Chitosan\u2010Based Drug Delivery System for Peri\u2010Implantitis Prevention"],"prefix":"10.1002","volume":"32","author":[{"given":"Nelly Senze","family":"Nnane","sequence":"first","affiliation":[{"name":"Institute for Technical Chemistry TU Braunschweig  Braunschweig Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Amit","family":"Gaikwad","sequence":"additional","affiliation":[{"name":"Department of Prosthetic Dentistry and Biomedical Materials Science Hannover Medical School  Hannover Germany"},{"name":"Institute of Transplant 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Hannover Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4915-7311","authenticated-orcid":false,"given":"Henning","family":"Menzel","sequence":"additional","affiliation":[{"name":"Institute for Technical Chemistry TU Braunschweig  Braunschweig Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,2,15]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0040-1715779"},{"issue":"20","key":"e_1_2_7_3_1","first-page":"S246","article-title":"Peri\u2010Implantitis","volume":"45","author":"Schwarz F.","year":"2018","journal-title":"Journal of Clinical 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