{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,19]],"date-time":"2026-08-19T19:18:32Z","timestamp":1787167112103,"version":"build-2736575974"},"reference-count":61,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2016,3,10]],"date-time":"2016-03-10T00:00:00Z","timestamp":1457568000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Peptoids, N-substituted glycine oligomers, are versatile peptidomimetics with diverse biomedical applications. However, strategies to the development of novel fluorescent peptoids as chemical sensors have not been extensively explored, yet. Here, we synthesized a novel peptoid-based fluorescent probe in which a coumarin moiety was incorporated via copper(I)-catalyzed azide-alkyne cycloaddition reaction. Fluorescence of the newly generated coumarin-peptoid was dramatically quenched upon coordination of the Cu2+ ion, and the resulting peptoid-Cu2+ complex exhibited significant Turn-ON fluorescence following the addition of CN\u2212. The rapid and reversible response, combined with cyanide selectivity of the synthesized peptoid, reflects a multistep photo-process and supports its utility as a new type of CN\u2212 sensor.<\/jats:p>","DOI":"10.3390\/molecules21030339","type":"journal-article","created":{"date-parts":[[2016,3,10]],"date-time":"2016-03-10T10:53:48Z","timestamp":1457607228000},"page":"339","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":26,"title":["A Peptoid-Based Fluorescent Sensor for Cyanide Detection"],"prefix":"10.3390","volume":"21","author":[{"given":"Bumhee","family":"Lim","sequence":"first","affiliation":[{"name":"College of Pharmacy, Research Institute of Pharmaceutical Sciences, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 151-742, Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jeeyeon","family":"Lee","sequence":"additional","affiliation":[{"name":"College of Pharmacy, Research Institute of Pharmaceutical Sciences, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 151-742, Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2016,3,10]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"9367","DOI":"10.1073\/pnas.89.20.9367","article-title":"Peptoids: A modular approach to drug discovery","volume":"89","author":"Simon","year":"1992","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"437","DOI":"10.1016\/S0076-6879(96)67027-X","article-title":"Synthesis of n-substituted glycine peptoid libraries","volume":"267","author":"Figliozzi","year":"1996","journal-title":"Methods Enzymol."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"5282","DOI":"10.3390\/molecules15085282","article-title":"Solid-phase synthesis of n-substituted glycine oligomers (\u03b1-peptoids) and derivatives","volume":"15","author":"Culf","year":"2010","journal-title":"Molecules"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"521","DOI":"10.1021\/jm701195j","article-title":"Modulation of cellular apoptosis with apoptotic protease-activating factor 1 (\u03b1-1) inhibitors","volume":"51","author":"Mondragon","year":"2008","journal-title":"J. Med. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"5744","DOI":"10.1021\/ja711193x","article-title":"A peptoid \u201cantibody surrogate\u201d that antagonizes vegf receptor 2 activity","volume":"130","author":"Udugamasooriya","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"2678","DOI":"10.1021\/jm00043a007","article-title":"Discovery of nanomolar ligands for 7-transmembrane g-protein-coupled receptors from a diverse n-(substituted)glycine peptoid library","volume":"37","author":"Zuckermann","year":"1994","journal-title":"J. Med. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1995","DOI":"10.1021\/ja056344c","article-title":"Probing the structural requirements of peptoids that inhibit HDM2-p53 interactions","volume":"128","author":"Hara","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"30","DOI":"10.1016\/j.neulet.2008.04.097","article-title":"Intranasal administration delivers peptoids to the rat central nervous system","volume":"439","author":"Ross","year":"2008","journal-title":"Neurosci. Lett."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"56","DOI":"10.1039\/B810875G","article-title":"Metallopeptoids","volume":"7","author":"Maayan","year":"2009","journal-title":"Chem. Commun."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1508","DOI":"10.1039\/b817980h","article-title":"Structure-function relationships in peptoids: Recent advances toward deciphering the structural requirements for biological function","volume":"7","author":"Fowler","year":"2009","journal-title":"Org. Biomol. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1497","DOI":"10.1039\/b518247f","article-title":"Clickity-click: Highly functionalized peptoid oligomers generated by sequential conjugation reactions on solid-phase support","volume":"4","author":"Holub","year":"2006","journal-title":"Org. Biomol. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2835","DOI":"10.1021\/ja312532x","article-title":"Cis-trans amide bond rotamers in \u03b2-peptoids and peptoids: Evaluation of stereoelectronic effects in backbone and side chains","volume":"135","author":"Laursen","year":"2013","journal-title":"J. Am. Chem. Soc."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"7927","DOI":"10.1002\/chem.201100216","article-title":"Chemical modulation of peptoids: Synthesis and conformational studies on partially constrained derivatives","volume":"17","author":"Moure","year":"2011","journal-title":"Chemistry"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"9553","DOI":"10.1021\/ja302342h","article-title":"The click triazolium peptoid side chain: A strong cis-amide inducer enabling chemical diversity","volume":"134","author":"Caumes","year":"2012","journal-title":"J. Am. Chem. Soc."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"627","DOI":"10.1002\/bip.21605","article-title":"Use of the environmentally sensitive fluorophore 4-N,N-dimethylamino-1,8-naphthalimide to study peptoid helix structures","volume":"96","author":"Fuller","year":"2011","journal-title":"Biopolymers"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"4999","DOI":"10.1021\/ol702208y","article-title":"Highly sensitive fluorescent probes for zinc ion based on triazolyl-containing tetradentate coordination motifs","volume":"9","author":"Huang","year":"2007","journal-title":"Org. Lett."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"5536","DOI":"10.1021\/ja909148v","article-title":"Direct detection of nitroxyl in aqueous solution using a tripodal copper(II) bodipy complex","volume":"132","author":"Rosenthal","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"3187","DOI":"10.1021\/ja970033n","article-title":"A multinuclear Ca2+ complex of a linear n-protected glycyl-dipeptoid derivative","volume":"119","author":"Jefferson","year":"1997","journal-title":"J. Am. Chem. Soc."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"8847","DOI":"10.1021\/ja802125x","article-title":"Biomimetic nanostructures: Creating a high-affinity zinc-binding site in a folded nonbiological polymer","volume":"130","author":"Lee","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"5699","DOI":"10.1002\/ejoc.200900637","article-title":"Conformational control in metallofoldamers: Design, synthesis and structural properties","volume":"2009","author":"Maayan","year":"2009","journal-title":"Eur. J. Org. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"598","DOI":"10.1021\/ol3034143","article-title":"Structural effects of proline substitution and metal binding on hexameric cyclic peptoids","volume":"15","author":"Izzo","year":"2013","journal-title":"Org. Lett."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"17488","DOI":"10.1021\/ja408788t","article-title":"Selective chromium(VI) ligands identified using combinatorial peptoid libraries","volume":"135","author":"Knight","year":"2013","journal-title":"J. Am. Chem. Soc."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"461","DOI":"10.1055\/s-0034-1378938","article-title":"Click to bind: Microwave-assisted solid-phase synthesis of peptoids incorporating pyridine\u2013triazole ligands and their copper(II) complexes","volume":"26","author":"Maayan","year":"2014","journal-title":"Synlett"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"407","DOI":"10.1002\/bip.22528","article-title":"Rapid identification of metal-binding peptoid oligomers by on-resin x-ray fluorescence screening","volume":"102","author":"Nalband","year":"2014","journal-title":"Biopolymers"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"4042","DOI":"10.1039\/C5SC00676G","article-title":"Development of peptoid-based ligands for the removal of cadmium from biological media","volume":"6","author":"Knight","year":"2015","journal-title":"Chem. Sci."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"11096","DOI":"10.1039\/C5CC04266F","article-title":"Metallopeptoids as efficient biomimetic catalysts","volume":"51","author":"Prathap","year":"2015","journal-title":"Chem. Commun."},{"key":"ref_27","doi-asserted-by":"crossref","unstructured":"Baskin, M., and Maayan, G. (2016). A rationally designed metal-binding helical peptoid for selective recognition processes. Chem. Sci.","DOI":"10.1039\/C5SC04358A"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.ccr.2014.02.014","article-title":"Nmr investigations of metal interactions with unstructured soluble protein domains","volume":"269","author":"Potocki","year":"2014","journal-title":"Coord. Chem. Rev."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"5142","DOI":"10.1039\/c1cc10672d","article-title":"An iminocoumarin-cu(II) ensemble-based chemodosimeter toward thiols","volume":"47","author":"Jung","year":"2011","journal-title":"Chem. Commun."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"4764","DOI":"10.1039\/c2cc30963g","article-title":"Coumarin-derived transformable fluorescent sensor for Zn2+","volume":"48","author":"Xu","year":"2012","journal-title":"Chem. Commun."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"717","DOI":"10.1039\/C2OB26955D","article-title":"Coumarin-dpa-cu(II) as a chemosensing ensemble towards histidine determination in urine and serum","volume":"11","author":"Hou","year":"2013","journal-title":"Org. Biomol. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"4434","DOI":"10.1039\/C4NJ00695J","article-title":"A coumarin-based sensitive and selective fluorescent sensor for copper(II) ions","volume":"38","author":"Yeh","year":"2014","journal-title":"New J. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","unstructured":"Kim, M.J., Swamy, K.M., Lee, K.M., Jagdale, A.R., Kim, Y., Kim, S.J., Yoo, K.H., and Yoon, J. (2009). Pyrophosphate selective fluorescent chemosensors based on coumarin-DPA-Cu(II) complexes. Chem. Commun., 7215\u20137217.","DOI":"10.1039\/b913809a"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1358","DOI":"10.3390\/s140101358","article-title":"Coumarin-based fluorescent probes for dual recognition of copper(II) and iron(III) ions and their application in bio-imaging","volume":"14","author":"Cassels","year":"2014","journal-title":"Sensors"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"117","DOI":"10.1016\/j.ejmech.2012.10.010","article-title":"Synthesis, biological evaluation and molecular docking studies of 3-(triazolyl)-coumarin derivatives: Effect on inducible nitric oxide synthase","volume":"58","author":"Stefani","year":"2012","journal-title":"Eur. J. Med. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"799","DOI":"10.1016\/j.bmcl.2013.12.095","article-title":"Synthesis and biological evaluation of 4-(1,2,3-triazol-1-yl)coumarin derivatives as potential antitumor agents","volume":"24","author":"Zhang","year":"2014","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"956","DOI":"10.1016\/j.bmcl.2010.12.059","article-title":"Synthesis and evaluation of a class of new coumarin triazole derivatives as potential antimicrobial agents","volume":"21","author":"Shi","year":"2011","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"5770","DOI":"10.1039\/c2an36076d","article-title":"Design and synthesis of triazolyl coumarins as Hg2+ selective fluorescent chemosensors","volume":"137","author":"Ho","year":"2012","journal-title":"Analyst"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"1290","DOI":"10.1021\/ol103077q","article-title":"Visualization of nitroxyl in living cells by a chelated copper(II) coumarin complex","volume":"13","author":"Zhou","year":"2011","journal-title":"Org. Lett."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"4252","DOI":"10.1038\/srep04252","article-title":"Substitution pattern reverses the fluorescence response of coumarin glycoligands upon coordination with silver(I)","volume":"4","author":"Shi","year":"2014","journal-title":"Sci. Rep."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"7229","DOI":"10.1021\/ic1009994","article-title":"Conformationally constrained (coumarin-triazolyl-bipyridyl) click fluoroionophore as a selective Al3+ sensor","volume":"49","author":"Maity","year":"2010","journal-title":"Inorg. Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"127","DOI":"10.1039\/B907368J","article-title":"Sensors for the optical detection of cyanide ion","volume":"39","author":"Xu","year":"2010","journal-title":"Chem. Soc. Rev."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"5056","DOI":"10.1021\/ol2018856","article-title":"Coumarin-cu(II) ensemble-based cyanide sensing chemodosimeter","volume":"13","author":"Jung","year":"2011","journal-title":"Org. Lett."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"121","DOI":"10.1002\/asia.201301144","article-title":"Pyridinium-fused pyridinone: A novel \u201cturn-on\u201d fluorescent chemodosimeter for cyanide","volume":"9","author":"Li","year":"2014","journal-title":"Chem. Asian J."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"19077","DOI":"10.1039\/c4ra01598c","article-title":"Coumarin\u2013hemicyanine conjugates as novel reaction-based sensors for cyanide detection: Convenient synthesis and ict mechanism","volume":"4","author":"Peng","year":"2014","journal-title":"RSC Adv."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"1302","DOI":"10.1042\/bst0311302","article-title":"Novel peptoids for the detection and suppression of reactive oxygen and nitrogen species","volume":"31","author":"Fisher","year":"2003","journal-title":"Biochem. Soc. Trans."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"380","DOI":"10.1002\/bip.22242","article-title":"A fluorescent peptoid ph-sensor","volume":"100","author":"Fuller","year":"2013","journal-title":"Biopolymers"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"8841","DOI":"10.1021\/ja0352101","article-title":"Incorporation of unprotected heterocyclic side chains into peptoid oligomers via solid-phase submonomer synthesis","volume":"125","author":"Burkoth","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"4603","DOI":"10.1021\/ol047955x","article-title":"A fluorogenic 1,3-dipolar cycloaddition reaction of 3-azidocoumarins and acetylenes","volume":"6","author":"Sivakumar","year":"2004","journal-title":"Org. Lett."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"2395","DOI":"10.1002\/ejoc.201000042","article-title":"Click chemistry to fluorescent amino esters: Synthesis and spectroscopic studies","volume":"2010","author":"Li","year":"2010","journal-title":"Eur. J. Org. Chem."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"1515","DOI":"10.1021\/cr960386p","article-title":"Signaling recognition events with fluorescent sensors and switches","volume":"97","author":"Gunaratne","year":"1997","journal-title":"Chem. Rev."},{"key":"ref_52","doi-asserted-by":"crossref","unstructured":"Valeur, B., and Berberan-Santos, M.N. (2012). Molecular Fluorescence: Principles and Applications, Wiley-VCH. [2nd ed.].","DOI":"10.1002\/9783527650002"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"2045","DOI":"10.1016\/S0039-9140(96)01875-9","article-title":"Cyanide thermodynamics 2. Stability constants of copper(I) cyanide complexes in aqueous acetonitrile mixtures","volume":"43","author":"Kurnia","year":"1996","journal-title":"Talanta"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"14886","DOI":"10.1021\/jp308505p","article-title":"Base-induced phototautomerization in 7-hydroxy-4-(trifluoromethyl)coumarin","volume":"116","author":"Westlake","year":"2012","journal-title":"J. Phys. Chem. B"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"1045","DOI":"10.2116\/analsci.30.1045","article-title":"Solvent effect on the fluorescence response of hydroxycoumarin bearing a dipicolylamine binding site to metal ions","volume":"30","author":"Kobayashi","year":"2014","journal-title":"Anal. Sci."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"127","DOI":"10.1021\/jp0662202","article-title":"Excited-state proton transfer in 7-hydroxy-4-methylcoumarin along a hydrogen-bonded water wire","volume":"111","author":"Georgieva","year":"2007","journal-title":"J. Phys. Chem. A"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"6","DOI":"10.1246\/bcsj.56.6","article-title":"Excited-state reactions of coumarins in aqueous solutions. I. The phototautomerization of 7-hydroxycoumarin and its derivative","volume":"56","author":"Moriay","year":"1983","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"107","DOI":"10.1039\/B812458B","article-title":"Turn-on fluorescent cyanide sensor based on copper ion-modified cdte quantum dots","volume":"134","author":"Shang","year":"2009","journal-title":"Analyst"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"3869","DOI":"10.1039\/c3nj00800b","article-title":"A highly selective pyrene based \u201coff\u2013on\u201d fluorescent chemosensor for cyanide","volume":"37","author":"Wang","year":"2013","journal-title":"New J. Chem."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"14023","DOI":"10.1021\/ja047945r","article-title":"Two-metal ion, Ni(II) and Cu(II), binding alpha-helical coiled coil peptide","volume":"126","author":"Tanaka","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"79","DOI":"10.1039\/b419413f","article-title":"Nmr studies on Cu(II)-peptide complexes: Exchange kinetics and determination of structures in solution","volume":"1","author":"Gaggelli","year":"2005","journal-title":"Mol. 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