{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,23]],"date-time":"2026-07-23T15:07:56Z","timestamp":1784819276856,"version":"3.55.0"},"reference-count":53,"publisher":"MDPI AG","issue":"6","license":[{"start":{"date-parts":[[2024,6,6]],"date-time":"2024-06-06T00:00:00Z","timestamp":1717632000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Australian Research Council","award":["DP180102741"],"award-info":[{"award-number":["DP180102741"]}]},{"name":"Australian Research Council","award":["DP210101632"],"award-info":[{"award-number":["DP210101632"]}]},{"name":"Australian Research Council","award":["APP1099920"],"award-info":[{"award-number":["APP1099920"]}]},{"DOI":"10.13039\/501100000925","name":"National Health and Medical Research Council of Australia","doi-asserted-by":"publisher","award":["DP180102741"],"award-info":[{"award-number":["DP180102741"]}],"id":[{"id":"10.13039\/501100000925","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000925","name":"National Health and Medical Research Council of Australia","doi-asserted-by":"publisher","award":["DP210101632"],"award-info":[{"award-number":["DP210101632"]}],"id":[{"id":"10.13039\/501100000925","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000925","name":"National Health and Medical Research Council of Australia","doi-asserted-by":"publisher","award":["APP1099920"],"award-info":[{"award-number":["APP1099920"]}],"id":[{"id":"10.13039\/501100000925","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Indonesia Endowment Fund for Education Scholarship","award":["DP180102741"],"award-info":[{"award-number":["DP180102741"]}]},{"name":"Indonesia Endowment Fund for Education Scholarship","award":["DP210101632"],"award-info":[{"award-number":["DP210101632"]}]},{"name":"Indonesia Endowment Fund for Education Scholarship","award":["APP1099920"],"award-info":[{"award-number":["APP1099920"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Biomolecules"],"abstract":"<jats:p>Selective staining of extracellular vesicles (EVs) is a major challenge for diagnostic and therapeutic applications. Herein, the EV labeling properties of a new class of tetranuclear polypyridylruthenium(II) complexes, Rubb7-TNL and Rubb7-TL, as phosphorescent stains are described. These new stains have many advantages over standard stains to detect and characterize EVs, including: high specificity for EV staining versus cell staining; high phosphorescence yields; photostability; and a lack of leaching from EVs until incorporation with target cells. As an example of their utility, large EVs released from control (basal) or lipopolysaccharide (LPS)-stimulated THP-1 monocytic leukemia cells were studied as a model of immune system EVs released during bacterial infection. Key findings from EV staining combined with flow cytometry were as follows: (i) LPS-stimulated THP-1 cells generated significantly larger and more numerous large EVs, as compared with those from unstimulated cells; (ii) EVs retained native EV physical properties after staining; and (iii) the new stains selectively differentiated intact large EVs from artificial liposomes, which are models of cell membrane fragments or other lipid-containing debris, as well as distinguished two distinct subpopulations of monocytic EVs within the same experiment, as a result of biochemical differences between unstimulated and LPS-stimulated monocytes. Comparatively, the staining patterns of A549 epithelial lung carcinoma-derived EVs closely resembled those of THP-1 cell line-derived EVs, which highlighted similarities in their selective staining despite their distinct cellular origins. This is consistent with the hypothesis that these new phosphorescent stains target RNA within the EVs.<\/jats:p>","DOI":"10.3390\/biom14060664","type":"journal-article","created":{"date-parts":[[2024,6,6]],"date-time":"2024-06-06T06:40:26Z","timestamp":1717656026000},"page":"664","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Tetranuclear Polypyridylruthenium(II) Complexes as Selective Nucleic Acid Stains for Flow Cytometric Analysis of Monocytic and Epithelial Lung Carcinoma Large Extracellular Vesicles"],"prefix":"10.3390","volume":"14","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-9718-1028","authenticated-orcid":false,"given":"Kartika","family":"Wardhani","sequence":"first","affiliation":[{"name":"School of Chemistry, The University of Sydney, Sydney, NSW 2006, Australia"},{"name":"Biochemistry and Biotechnology (B-TEK) Group, Bioscience Division, Los Alamos National Laboratory, Los Alamos, NM 87545, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7311-3263","authenticated-orcid":false,"given":"Aviva","family":"Levina","sequence":"additional","affiliation":[{"name":"School of Chemistry, The University of Sydney, Sydney, NSW 2006, Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Biyun","family":"Sun","sequence":"additional","affiliation":[{"name":"School of Natural Sciences, Faculty of Science and Engineering, Macquarie University, Sydney, NSW 2109, Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Haipei","family":"Zou","sequence":"additional","affiliation":[{"name":"School of Chemistry, The University of Sydney, Sydney, NSW 2006, Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0442-0462","authenticated-orcid":false,"given":"Georges E. R.","family":"Grau","sequence":"additional","affiliation":[{"name":"Sydney Nano, The University of Sydney, Sydney, NSW 2006, Australia"},{"name":"Sydney Cancer Network, The University of Sydney, Sydney, NSW 2006, Australia"},{"name":"Marie Bashir Institute, The University of Sydney, Sydney, NSW 2006, Australia"},{"name":"Vascular Immunology Unit, School of Medical Sciences, Faculty of Medicine and Health, The University of Sydney, Sydney, NSW 2006, Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7759-0465","authenticated-orcid":false,"given":"F. Richard","family":"Keene","sequence":"additional","affiliation":[{"name":"Discipline of Chemistry, School of Physics, Chemistry, and Earth Sciences, The University of Adelaide, Adelaide, SA 5005, Australia"},{"name":"Australian Institute of Tropical Health and Medicine\/Centre for Molecular Therapeutics, James Cook University, Townsville, QLD 4811, Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"J. Grant","family":"Collins","sequence":"additional","affiliation":[{"name":"School of Science, The University of New South Wales, Australian Defence Force Academy, Canberra, ACT 2612, Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3232-2720","authenticated-orcid":false,"given":"Peter A.","family":"Lay","sequence":"additional","affiliation":[{"name":"School of Chemistry, The University of Sydney, Sydney, NSW 2006, Australia"},{"name":"Sydney Nano, The University of Sydney, Sydney, NSW 2006, Australia"},{"name":"Sydney Cancer Network, The University of Sydney, Sydney, NSW 2006, Australia"},{"name":"Marie Bashir Institute, The University of Sydney, Sydney, NSW 2006, Australia"},{"name":"Sydney Analytical, The University of Sydney, Sydney, NSW 2006, Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,6,6]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1535750","DOI":"10.1080\/20013078.2018.1535750","article-title":"Minimal information for studies of extracellular vesicles 2018 (MISEV2018): A position statement of the International Society for Extracellular Vesicles and update of the MISEV2014 guidelines","volume":"7","author":"Witwer","year":"2018","journal-title":"J. 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