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Cartilage is an avascular tissue with a dense matrix constraining the penetration of imaging and targeting agents. Here, a unique class of cationic peptidomimetics featuring peptoid residue Nlys (N\u2010substituted butyl\u2010amino glycine) is reported for cartilage targeting. Sulfo\u2010Cyanine5 (Cy5) labeled Nlys\u2010rich sequences are found to penetrate and be retained within millimeter\u2010deep cartilage plugs in vitro by specific binding to the tissue's polyanionic glycosaminoglycan (GAG) chains. Owing to the unnatural sequences being undegradable by common proteases, these Nlys\u2010peptidomimetics overcome the problem of low serum stability of existing benchmark cartilage\u2010binding peptides (e.g., octa\u2010arginine) and allow systemic administration. Intravenously delivered Cy5\u2010(NlysO)\n                    <jats:sub>7<\/jats:sub>\n                    (O: hydroxyproline) is taken up by the cartilage across the body of living mice and zebrafish, enabling whole\u2010body 3D light\u2010sheet microscopy scans of neonatal mice undergoing bone development as well as in vivo detection of GAG loss in mice's aged knee joints and inflamed RA ankles. The Nlys\u2010compounds also show no cytotoxicity in chondrocytes and good biocompatibility in vivo, paving the way for applications in GAG\u2010targeted molecular imaging, drug delivery, and biomaterials for cartilage\u2010related diseases.\n                  <\/jats:p>","DOI":"10.1002\/advs.202502781","type":"journal-article","created":{"date-parts":[[2025,8,31]],"date-time":"2025-08-31T17:21:42Z","timestamp":1756660902000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Cationic Peptoids for Systemic In Vivo Cartilage\u2010Targeting"],"prefix":"10.1002","volume":"12","author":[{"given":"Chaonan","family":"Zhang","sequence":"first","affiliation":[{"name":"Guangdong Provincial Engineering Research Center of Molecular Imaging Guangdong\u2010Hong Kong\u2010Macao University Joint Laboratory of Interventional Medicine the Fifth Affiliated Hospital Sun Yat\u2010sen University  Zhuhai Guangdong 519000 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