{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,3]],"date-time":"2026-10-03T10:29:27Z","timestamp":1791023367886,"version":"4.1.0"},"reference-count":147,"publisher":"Wiley","issue":"35","license":[{"start":{"date-parts":[[2006,9,5]],"date-time":"2006-09-05T00:00:00Z","timestamp":1157414400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2006,12,4]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A new fluorescent probe for Zn<jats:sup>2+<\/jats:sup>, namely, 8\u2010hydroxy\u20105\u2010<jats:italic>N<\/jats:italic>,<jats:italic>N<\/jats:italic>\u2010dimethylaminosulfonylquinolin\u20102\u2010ylmethyl\u2010pendant cyclen (L<jats:sup>8<\/jats:sup>), was designed and synthesized (cyclen=1,4,7,10\u2010tetraazacyclododecane). By potentiometric pH, <jats:sup>1<\/jats:sup>H NMR, and UV spectroscopic titrations, the deprotonation constants p<jats:italic>K<\/jats:italic><jats:sub>a1<\/jats:sub>\u2013p<jats:italic>K<\/jats:italic><jats:sub>a6<\/jats:sub> of L<jats:sup>8<\/jats:sup>\u22c54\u2009HCl were determined to be &lt;2, &lt;2, &lt;2 (for amino groups of the cyclen and quinoline moieties), 7.19\u00b10.05 (for 8\u2010OH of the quinoline moiety), 10.10\u00b10.05, and 11.49\u00b10.05, respectively, at 25\u2009\u00b0C with <jats:italic>I<\/jats:italic>=0.1 (NaNO<jats:sub>3<\/jats:sub>). The results of <jats:sup>1<\/jats:sup>H NMR, potentiometric pH, and UV titrations, as well as single\u2010crystal X\u2010ray diffraction analysis, showed that L<jats:sup>8<\/jats:sup> and Zn<jats:sup>2+<\/jats:sup> form a 1:1 complex [Zn(H<jats:sub>\u22121<\/jats:sub>L<jats:sup>8<\/jats:sup>)], in which the 8\u2010OH group of the quinoline ring of L<jats:sup>8<\/jats:sup> is deprotonated and coordinates to Zn<jats:sup>2+<\/jats:sup>, in aqueous solution at neutral pH. On addition of one equivalent of Zn<jats:sup>2+<\/jats:sup> and Cd<jats:sup>2+<\/jats:sup>, the fluorescence emission of L<jats:sup>8<\/jats:sup> (5 \u03bc<jats:sc>M<\/jats:sc>) at 512 nm in aqueous solution at pH 7.4 [10 m<jats:sc>M<\/jats:sc> HEPES with <jats:italic>I<\/jats:italic>=0.1 (NaNO<jats:sub>3<\/jats:sub>)] and 25\u2009\u00b0C increased by factors of 17 and 43, respectively. We found that the cyclen moiety has the unique property of quenching the fluorescence emission of the quinolinol moiety when not complexed with metal cations, but enhancing emission when complexed with Zn<jats:sup>2+<\/jats:sup> or Cd<jats:sup>2+<\/jats:sup>. In addition, the Zn<jats:sup>2+<\/jats:sup>\u2013L<jats:sup>8<\/jats:sup> complex [Zn(H<jats:sub>\u22121<\/jats:sub>L<jats:sup>8<\/jats:sup>)] is much more thermodynamically and kinetically stable (<jats:italic>K<\/jats:italic><jats:sub>d<\/jats:sub>{Zn(H<jats:sub>\u22121<\/jats:sub>L<jats:sup>8<\/jats:sup>)}=[Zn<jats:sup>2+<\/jats:sup>]<jats:sub>free<\/jats:sub>[L<jats:sup>8<\/jats:sup>]<jats:sub>free<\/jats:sub>\/[Zn(H<jats:sub>\u22121<\/jats:sub>L<jats:sup>8<\/jats:sup>)]=8 f<jats:sc>M<\/jats:sc> at pH 7.4) than the Zn<jats:sup>2+<\/jats:sup> complexes of our previous Zn<jats:sup>2+<\/jats:sup> fluorophores ([Zn(H<jats:sub>\u22121<\/jats:sub>L<jats:sup>2<\/jats:sup>)] and [Zn(L<jats:sup>3<\/jats:sup>)]). Furthermore, formation of [Zn(H<jats:sub>\u22121<\/jats:sub>L<jats:sup>8<\/jats:sup>)] is much faster than those of [Zn(H<jats:sub>\u22121<\/jats:sub>L<jats:sup>2<\/jats:sup>)] and [Zn(L<jats:sup>3<\/jats:sup>)]. The staining of early\u2010stage apoptotic cells with L<jats:sup>8<\/jats:sup> is also described.<\/jats:p>","DOI":"10.1002\/chem.200600379","type":"journal-article","created":{"date-parts":[[2006,9,5]],"date-time":"2006-09-05T04:06:19Z","timestamp":1157429179000},"page":"9066-9080","source":"Crossref","is-referenced-by-count":81,"title":["A New Fluorescent Probe for Zinc(II): An 8\u2010Hydroxy\u20105\u2010<i>N<\/i>,<i>N<\/i>\u2010dimethylaminosulfonylquinoline\u2010Pendant 1,4,7,10\u2010Tetraazacyclododecane"],"prefix":"10.1002","volume":"12","author":[{"given":"Shin","family":"Aoki","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kazusa","family":"Sakurama","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nanako","family":"Matsuo","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yasuyuki","family":"Yamada","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ryoko","family":"Takasawa","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sei\u2010ichi","family":"Tanuma","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Motoo","family":"Shiro","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kei","family":"Takeda","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Eiichi","family":"Kimura","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2006,11,27]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","volume-title":"The Biological Chemistry of the Elements","author":"Silva J. 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The intrinsic log\u2009Ks([Cu(H\u22121L8)]) was too large to be determined by potentiometric pH titrations."},{"key":"e_1_2_6_123_2","unstructured":"For emission intensities of12([Zn(H\u22121L8)] 5 \u03bcM) at 512 nm in the pH range of 4.5\u201311 seeSupporting Information."},{"key":"e_1_2_6_124_2","unstructured":"\u00a0"},{"key":"e_1_2_6_125_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.8171316"},{"key":"e_1_2_6_126_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.281.5381.1317"},{"key":"e_1_2_6_127_2","unstructured":"\u00a0"},{"key":"e_1_2_6_128_2","doi-asserted-by":"publisher","DOI":"10.1016\/0006-291X(91)91278-K"},{"key":"e_1_2_6_129_2","doi-asserted-by":"publisher","DOI":"10.1016\/0014-4827(92)90393-M"},{"key":"e_1_2_6_130_2","doi-asserted-by":"publisher","DOI":"10.1042\/bj3260675"},{"key":"e_1_2_6_131_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0169-328X(01)00135-8"},{"key":"e_1_2_6_132_2","doi-asserted-by":"publisher","DOI":"10.1016\/0022-1759(95)00072-I"},{"key":"e_1_2_6_133_2","unstructured":"\u00a0"},{"key":"e_1_2_6_134_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2004.08.052"},{"key":"e_1_2_6_135_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.200500149"},{"key":"e_1_2_6_136_2","doi-asserted-by":"publisher","DOI":"10.1042\/bj3490255"},{"key":"e_1_2_6_137_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-1759(01)00562-2"},{"key":"e_1_2_6_138_2","unstructured":"For fluorescence Cd2+sensors see"},{"key":"e_1_2_6_139_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00175a046"},{"key":"e_1_2_6_140_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0003-2670(99)00154-3"},{"key":"e_1_2_6_141_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0020-1693(99)00565-4"},{"key":"e_1_2_6_142_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)00330-6"},{"key":"e_1_2_6_143_2","doi-asserted-by":"publisher","DOI":"10.1039\/b108300g"},{"key":"e_1_2_6_144_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2004.05.075"},{"key":"e_1_2_6_145_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol035484t"},{"key":"e_1_2_6_146_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2004.08.047"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.200600379","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.200600379","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T23:58:35Z","timestamp":1760313515000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.200600379"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2006,11,27]]},"references-count":147,"journal-issue":{"issue":"35","published-print":{"date-parts":[[2006,12,4]]}},"alternative-id":["10.1002\/chem.200600379"],"URL":"https:\/\/doi.org\/10.1002\/chem.200600379","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2006,11,27]]}}}