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Phosphonium\u2010 or nitrogen cation\u2010based MTMs are not inert vectors and exhibit intrinsic bioactivity on mitochondrial and cellular levels to various extents. Here, we systematically evaluated a panel of N\n                    <jats:sup>+<\/jats:sup>\n                    \u2010based cations to determine how structural features influence subcellular distribution and inherent bioactivity. Live\u2010cell imaging of fluorescent dye conjugates revealed that 3,5\u2010diphenylpyridinium (DPPy\n                    <jats:sup>+<\/jats:sup>\n                    ) exhibits cellular uptake and mitochondrial targeting comparable to the benchmark triphenylphosphonium (TPP\n                    <jats:sup>+<\/jats:sup>\n                    ), whereas conjugates with unsubstituted pyridinium preferentially accumulate in lysosomes. Profiling of inert cargo derivatives showed that DPPy\n                    <jats:sup>+<\/jats:sup>\n                    has lower intrinsic activity on mitochondrial membrane potential and oxidative phosphorylation, as well as on cellular respiration and viability than TPP\n                    <jats:sup>+<\/jats:sup>\n                    . The combination of efficient mitochondrial delivery and low intrinsic bioactivity translated to bioactive cargo: a Kv1.3 inhibitor conjugate with DPPy\n                    <jats:sup>+<\/jats:sup>\n                    induced apoptosis in cancer cell lines and demonstrated improved cancer selectivity relative to the TPP\n                    <jats:sup>+<\/jats:sup>\n                    conjugate in pancreatic organoid models. These results position lipophilic pyridinium cations as effective TPP\n                    <jats:sup>+<\/jats:sup>\n                    surrogates with enhanced biocompatibility for mitochondria\u2010targeted therapeutic and diagnostic agents, while revealing the structure\u2010dependent competing lysosomal accumulation of permanent nitrogen cations.\n                  <\/jats:p>","DOI":"10.1002\/anie.7158257","type":"journal-article","created":{"date-parts":[[2026,5,20]],"date-time":"2026-05-20T08:02:21Z","timestamp":1779264141000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Mitochondria\u2010Targeting Moieties Based on N\u2010Tethered Pyridinium Cations"],"prefix":"10.1002","volume":"65","author":[{"ORCID":"https:\/\/orcid.org\/0009-0009-7943-4031","authenticated-orcid":false,"given":"Ivan","family":"D\u017eaji\u0107","sequence":"first","affiliation":[{"name":"Faculty of Pharmacy University of Ljubljana  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