{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,21]],"date-time":"2026-09-21T19:00:27Z","timestamp":1790017227337,"version":"4.0.1"},"reference-count":53,"publisher":"Wiley","issue":"11","license":[{"start":{"date-parts":[[2015,6,26]],"date-time":"2015-06-26T00:00:00Z","timestamp":1435276800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001700","name":"MEXT","doi-asserted-by":"crossref","id":[{"id":"10.13039\/501100001700","id-type":"DOI","asserted-by":"crossref"}]},{"name":"Toray Science Foundation"},{"name":"JSPS"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemBioChem"],"published-print":{"date-parts":[[2015,7,27]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>We report the design and development of a fluorescent Cd<jats:sup>II<\/jats:sup> ion complex that is capable of the ratiometric detection of H<jats:sub>2<\/jats:sub>S in living cells. This probe exploits the metal\u2010ion\u2010induced emission red shift resulting from direct contact between the aromatic ring of a fluorophore and a metal ion (i.e., arene\u2013metal\u2010ion or \u201cAM\u201d contact). The Cd<jats:sup>II<\/jats:sup> complex displays a large emission blue shift upon interaction with H<jats:sub>2<\/jats:sub>S as the Cd<jats:sup>II<\/jats:sup>\u2010free ligand is released by the formation of cadmium sulfide. Screening of potential ligands and fluorophores led to the discovery of a pyronine\u2010type probe, <jats:bold>6\u22c5<\/jats:bold>Cd<jats:sup>II<\/jats:sup>, that generated a sensitive and rapid ratio value change upon interaction with H<jats:sub>2<\/jats:sub>S, without interference from the glutathione that is abundant in the cell. The membrane\u2010impermeable <jats:bold>6\u22c5<\/jats:bold>Cd<jats:sup>II<\/jats:sup> was successfully translocated into live cells by using an oligo\u2010arginine peptide and pyrenebutylate as carriers. As such, <jats:bold>6\u22c5<\/jats:bold>Cd<jats:sup>II<\/jats:sup> was successfully applied to the ratiometric detection of both exogenous and endogenous H<jats:sub>2<\/jats:sub>S produced by the enzymes in living cells, thus demonstrating the utility of <jats:bold>6\u22c5<\/jats:bold>Cd<jats:sup>II<\/jats:sup> in biological fluorescence analysis.<\/jats:p>","DOI":"10.1002\/cbic.201500249","type":"journal-article","created":{"date-parts":[[2015,5,28]],"date-time":"2015-05-28T10:18:57Z","timestamp":1432808337000},"page":"1608-1615","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["Rational Design of a Ratiometric Fluorescent Probe Based on Arene\u2013Metal\u2010Ion Contact for Endogenous Hydrogen Sulfide Detection in Living Cells"],"prefix":"10.1002","volume":"16","author":[{"given":"Ryosuke","family":"Kawagoe","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ippei","family":"Takashima","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kazuteru","family":"Usui","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anna","family":"Kanegae","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yusuke","family":"Ozawa","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Akio","family":"Ojida","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2015,6,26]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1038\/nrd2425"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1321232111"},{"key":"e_1_2_6_4_2","unstructured":"\u00a0"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1162667"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1093\/emboj\/20.21.6008"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchembio.1018"},{"key":"e_1_2_6_8_2","unstructured":"\u00a0"},{"key":"e_1_2_6_9_2","doi-asserted-by":"crossref","first-page":"1066","DOI":"10.1523\/JNEUROSCI.16-03-01066.1996","volume":"16","author":"Kazuho A.","year":"1996","journal-title":"J. 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The planer conformation of6\u2032 might facilitate conjugation of the sp2lone pairs of the pyrroridine nitrogens with the pyronine ring so that the LUMO energy level of6\u2032 is higher than that of7\u2032."},{"key":"e_1_2_6_40_2","unstructured":"\u00a0"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1039\/ft9949001727"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00053a046"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.addr.2004.10.009"},{"key":"e_1_2_6_44_2","unstructured":"\u00a0"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja043633c"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/cb600127m"},{"key":"e_1_2_6_47_2","unstructured":"Treatment of HeLa cells with the CdII\u22c5pyrithione complex (10 \u03bcM) and Na2S (150 \u03bcM) for 1 h did not lead to a significant change in cell viability (Figure S7) thus suggesting that CdIIreleased from6\u22c5CdIIas Na2S exerts little toxicity on the cells."},{"key":"e_1_2_6_48_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0908047106"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.1172\/JCI119868"},{"key":"e_1_2_6_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol016400o"}],"container-title":["ChemBioChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fcbic.201500249","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbic.201500249","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T21:05:15Z","timestamp":1760303115000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cbic.201500249"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2015,6,26]]},"references-count":53,"journal-issue":{"issue":"11","published-print":{"date-parts":[[2015,7,27]]}},"alternative-id":["10.1002\/cbic.201500249"],"URL":"https:\/\/doi.org\/10.1002\/cbic.201500249","archive":["Portico"],"relation":{},"ISSN":["1439-4227","1439-7633"],"issn-type":[{"value":"1439-4227","type":"print"},{"value":"1439-7633","type":"electronic"}],"subject":[],"published":{"date-parts":[[2015,6,26]]},"assertion":[{"value":"2015-05-17","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2015-06-26","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}