{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T04:49:34Z","timestamp":1791262174149,"version":"4.1.0"},"reference-count":46,"publisher":"Wiley","issue":"33","license":[{"start":{"date-parts":[[2013,6,28]],"date-time":"2013-06-28T00:00:00Z","timestamp":1372377600000},"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":[[2013,8,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Chiral quantum dots (QDs), differing in their core or shell size and, consequently, in their optical properties, were synthesized by the treatment of commercially available amine\u2010capped quantum dots with methyl ester <jats:italic>N<\/jats:italic>\u2010acetyl\u2010<jats:sc>L<\/jats:sc>\u2010cysteine (CysP). Interestingly, their colloidal methanol solutions remain stable for several months. Their NMR and IR spectra were in accordance with CysP binding to the QD surface through two anchoring groups; its thiolate (strongly bound) and the carbonyl group of its ester (weaker bound) group, whereas their circular dichroism (CD) spectra showed a new broad redshifted band, suggesting that the attachment to the QD surface modified the conformational equilibrium towards conformer(s) with optical activity in this region. These QDs were sufficiently fluorescent to perform studies of the chiral recognition of drugs, in particular the aryl propionic acids (APAs) ketoprofen (KP), naproxen (NP), flurbiprofen (FP), and ibuprofen (IP). We used different drug concentration ranges, depending on the QD solubility. All the assayed drugs quenched the QD emission in a concentration\u2010dependent mode. Quenching fluorescence assays with the chiral QDs (CS@CysP) showed their extraordinary capacity for the chiral recognition of KP, NP, and FP, and particularly in the case of KP and FP, a remarkable positive allosteric effect was detected for the <jats:italic>R<\/jats:italic> enantiomer. By using a drug\/CS@CysP molar ratio of 5000:1 and 2500:1, the changes of intensity and the sign of the CD spectrum of the drug evidenced the dissociation of the drug carboxylic group in the presence of the QD.<\/jats:p>","DOI":"10.1002\/chem.201300875","type":"journal-article","created":{"date-parts":[[2013,6,28]],"date-time":"2013-06-28T08:37:13Z","timestamp":1372408633000},"page":"11068-11076","source":"Crossref","is-referenced-by-count":59,"title":["Sensing Chiral Drugs by Using CdSe\/ZnS Nanoparticles Capped with <i>N<\/i>\u2010Acetyl\u2010<scp>L<\/scp>\u2010Cysteine Methyl Ester"],"prefix":"10.1002","volume":"19","author":[{"given":"Teresa","family":"Delgado\u2010P\u00e9rez","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lydia M.","family":"Bouchet","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Miguel","family":"de\u2005la\u2005Guardia","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Raquel E.","family":"Galian","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Julia","family":"P\u00e9rez\u2010Prieto","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2013,6,28]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr030673a"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0300284"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/3527607439"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma101660s"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/j100193a014"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1039\/b102376b"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20001016)39:20<3638::AID-ANIE3638>3.0.CO;2-G"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr030052h"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.solener.2008.10.001"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1104274"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1038\/nbt927"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/nl049170q"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ac0258251"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/b517613c"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1cc15312a"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/cm0700089"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/B414858D"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/nl900470p"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ac900034h"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/nn2044802"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja209981n"},{"key":"e_1_2_6_22_2","unstructured":"For other examples of preparation of chiral QDs by using a chiral stabilizer see:"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1039\/b704636g"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/nl801453g"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja906894r"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201103762"},{"key":"e_1_2_6_26_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201103762"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.aca.2006.06.039"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1039\/b509346e"},{"key":"e_1_2_6_29_2","unstructured":"Line broadening of the1H\u2005NMR signals of organic molecules capping core QDs is often observed and it is more pronounced for the hydrogen atom closest to the core; this effect is less important in core\/shell QDs see:"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1139\/V10-160"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja710909f"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja804414f"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/cphc.201200152"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja058717f"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/la703431j"},{"key":"e_1_2_6_36_2","unstructured":"The time needed depended on the CS@CysP\/drug combination and was studied for each combination by following the fluorescence changes after addition of several drug aliquots. The emission was registered between 10 and 90\u2005min after the addition of the drug which was longer than the time needed for equilibration of the emission."},{"key":"e_1_2_6_37_2","unstructured":"For an example of positive allosteric effect of an artificial receptor see:"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(19980803)110:15<2242::AID-ANGE2242>3.0.CO;2-K"},{"key":"e_1_2_6_38_3","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19980817)37:15<2096::AID-ANIE2096>3.0.CO;2-B"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bios.2004.03.036"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0832310100"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00707a024"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0003-2670(99)00811-9"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201008206"},{"key":"e_1_2_6_43_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201008206"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201300875","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201300875","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T21:27:24Z","timestamp":1760304444000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201300875"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,6,28]]},"references-count":46,"journal-issue":{"issue":"33","published-print":{"date-parts":[[2013,8,12]]}},"alternative-id":["10.1002\/chem.201300875"],"URL":"https:\/\/doi.org\/10.1002\/chem.201300875","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2013,6,28]]}}}