{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T02:05:27Z","timestamp":1760148327795,"version":"build-2065373602"},"reference-count":18,"publisher":"MDPI AG","issue":"8","license":[{"start":{"date-parts":[[2023,4,20]],"date-time":"2023-04-20T00:00:00Z","timestamp":1681948800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100000001","name":"National Science Foundation (NSF), CBET","doi-asserted-by":"publisher","award":["2102848"],"award-info":[{"award-number":["2102848"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Polymeric nanoparticles with reactive functional groups are an attractive platform for drug carriers that can be conjugated with drugs through a cleavable covalent linkage. Since the required functional groups vary depending on the drug molecule, there is a need for development of a novel post-modification method to introduce different functional groups to polymeric nanoparticles. We recently reported phenylboronic acid (PBA)-containing nanoparticles (BNP) with a unique framboidal morphology created via one-step aqueous dispersion polymerization. Since BNPs have high surface area due to their framboidal morphology and contain a high density of PBA groups, these particles can be used as nanocarriers for drugs that can bind to PBA groups such as curcumin and a catechol-bearing carbon monoxide donor. To further explore the potential of BNPs, in this article we report a novel strategy to introduce different functional groups to BNPs via the palladium-catalyzed Suzuki\u2013Miyaura cross-coupling reaction between the PBA groups and iodo- and bromo-coupling partners. We developed a new catalytic system that efficiently catalyzes Suzuki\u2013Miyaura reactions in water without the need for an organic solvent, as confirmed by NMR. Using this catalyst system, we show that BNPs can be functionalized with carboxylic acids, aldehyde, and hydrazide groups while keeping their original framboidal morphology as confirmed via IR, alizarin red assay, and TEM. Furthermore, the potential of the functionalized BNP in drug delivery applications was demonstrated by conjugating the hydrogen sulfide (H2S)-releasing compound anethole dithiolone to carboxylic acid-functionalized BNPs and show their H2S-releasing capability in cell lysate.<\/jats:p>","DOI":"10.3390\/molecules28083602","type":"journal-article","created":{"date-parts":[[2023,4,21]],"date-time":"2023-04-21T02:05:31Z","timestamp":1682042731000},"page":"3602","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Functionalization of Framboidal Phenylboronic Acid-Containing Nanoparticles via Aqueous Suzuki\u2013Miyaura Coupling Reactions"],"prefix":"10.3390","volume":"28","author":[{"given":"Andr\u00e9 J.","family":"van der Vlies","sequence":"first","affiliation":[{"name":"Department of Materials Science and Engineering, Pennsylvania State University, 331 Steidle Building, University Park, State College, PA 16801, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4189-7630","authenticated-orcid":false,"given":"Urara","family":"Hasegawa","sequence":"additional","affiliation":[{"name":"Department of Materials Science and Engineering, Pennsylvania State University, 331 Steidle Building, University Park, State College, PA 16801, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2023,4,20]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"4388","DOI":"10.1021\/acs.macromol.5b00574","article-title":"Dual Stimuli-Responsive Phenylboronic Acid-Containing Framboidal Nanoparticles by One-Step Aqueous Dispersion Polymerization","volume":"48","author":"Hasegawa","year":"2015","journal-title":"Macromolecules"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"2316","DOI":"10.1021\/ac030021m","article-title":"High Ionic Strength Glucose-Sensing Photonic Crystal","volume":"75","author":"Alexeev","year":"2003","journal-title":"Anal. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1174","DOI":"10.1016\/j.colsurfb.2015.11.011","article-title":"Mannose-displaying fluorescent framboidal nanoparticles containing phenylboronic acid groups as a potential drug carrier for macrophage targeting","volume":"136","author":"Hasegawa","year":"2015","journal-title":"Colloids Surf. B Biointerfaces"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1500","DOI":"10.1021\/acs.bioconjchem.6b00135","article-title":"Polymeric Framboidal Nanoparticles Loaded with a Carbon Monoxide Donor via Phenylboronic Acid-Catechol Complexation","volume":"27","author":"Inubushi","year":"2016","journal-title":"Bioconj. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"861","DOI":"10.1021\/acs.bioconjchem.9b00006","article-title":"Framboidal Nanoparticles Containing a Curcumin\u2013Phenylboronic Acid Complex with Antiangiogenic and Anticancer Activities","volume":"30","author":"Morisaki","year":"2019","journal-title":"Bioconj. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"147","DOI":"10.1016\/S0022-328X(98)01055-9","article-title":"Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995\u20131998","volume":"576","author":"Suzuki","year":"1999","journal-title":"J. Organomet. 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Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/8\/3602\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T19:19:58Z","timestamp":1760123998000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/8\/3602"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,4,20]]},"references-count":18,"journal-issue":{"issue":"8","published-online":{"date-parts":[[2023,4]]}},"alternative-id":["molecules28083602"],"URL":"https:\/\/doi.org\/10.3390\/molecules28083602","relation":{},"ISSN":["1420-3049"],"issn-type":[{"type":"electronic","value":"1420-3049"}],"subject":[],"published":{"date-parts":[[2023,4,20]]}}}