{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,2]],"date-time":"2026-06-02T15:07:46Z","timestamp":1780412866797,"version":"3.54.1"},"reference-count":36,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2022,10,10]],"date-time":"2022-10-10T00:00:00Z","timestamp":1665360000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Natural Science Foundation of China","award":["22078067"],"award-info":[{"award-number":["22078067"]}]},{"name":"National Natural Science Foundation of China","award":["32122003"],"award-info":[{"award-number":["32122003"]}]},{"name":"National Natural Science Foundation of China","award":["21807014"],"award-info":[{"award-number":["21807014"]}]},{"name":"National Natural Science Foundation of China","award":["JCYJ20180507181654823"],"award-info":[{"award-number":["JCYJ20180507181654823"]}]},{"name":"National Natural Science Foundation of China","award":["2020A1515011463"],"award-info":[{"award-number":["2020A1515011463"]}]},{"name":"National Natural Science Foundation of China","award":["2017GC010596"],"award-info":[{"award-number":["2017GC010596"]}]},{"name":"Science Technology and Innovation Committee of Shenzhen Municipality","award":["22078067"],"award-info":[{"award-number":["22078067"]}]},{"name":"Science Technology and Innovation Committee of Shenzhen Municipality","award":["32122003"],"award-info":[{"award-number":["32122003"]}]},{"name":"Science Technology and Innovation Committee of Shenzhen Municipality","award":["21807014"],"award-info":[{"award-number":["21807014"]}]},{"name":"Science Technology and Innovation Committee of Shenzhen Municipality","award":["JCYJ20180507181654823"],"award-info":[{"award-number":["JCYJ20180507181654823"]}]},{"name":"Science Technology and Innovation Committee of Shenzhen Municipality","award":["2020A1515011463"],"award-info":[{"award-number":["2020A1515011463"]}]},{"name":"Science Technology and Innovation Committee of Shenzhen Municipality","award":["2017GC010596"],"award-info":[{"award-number":["2017GC010596"]}]},{"name":"Guangdong Basic and Applied Basic Research Foundation","award":["22078067"],"award-info":[{"award-number":["22078067"]}]},{"name":"Guangdong Basic and Applied Basic Research Foundation","award":["32122003"],"award-info":[{"award-number":["32122003"]}]},{"name":"Guangdong Basic and Applied Basic Research Foundation","award":["21807014"],"award-info":[{"award-number":["21807014"]}]},{"name":"Guangdong Basic and Applied Basic Research Foundation","award":["JCYJ20180507181654823"],"award-info":[{"award-number":["JCYJ20180507181654823"]}]},{"name":"Guangdong Basic and Applied Basic Research Foundation","award":["2020A1515011463"],"award-info":[{"award-number":["2020A1515011463"]}]},{"name":"Guangdong Basic and Applied Basic Research Foundation","award":["2017GC010596"],"award-info":[{"award-number":["2017GC010596"]}]},{"name":"Pearl River Talent Plan of Guangdong Province","award":["22078067"],"award-info":[{"award-number":["22078067"]}]},{"name":"Pearl River Talent Plan of Guangdong Province","award":["32122003"],"award-info":[{"award-number":["32122003"]}]},{"name":"Pearl River Talent Plan of Guangdong Province","award":["21807014"],"award-info":[{"award-number":["21807014"]}]},{"name":"Pearl River Talent Plan of Guangdong Province","award":["JCYJ20180507181654823"],"award-info":[{"award-number":["JCYJ20180507181654823"]}]},{"name":"Pearl River Talent Plan of Guangdong Province","award":["2020A1515011463"],"award-info":[{"award-number":["2020A1515011463"]}]},{"name":"Pearl River Talent Plan of Guangdong Province","award":["2017GC010596"],"award-info":[{"award-number":["2017GC010596"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Biosensors"],"abstract":"<jats:p>Formaldehyde (FA) is involved in multiple physiological regulatory processes and plays a crucial role in memory storage. Meanwhile, FA has a notorious reputation as a toxic compound, and it will cause a variety of diseases if its level is unbalanced in the human body. To date, there have been numerous fluorescent probes for FA imaging reported. Among them, the probes based on the 2\u2212aza\u2212Cope rearrangement have attracted the most attention, and their applications in cell imaging have been greatly expanded. Herein, we screened the various trigger moieties of FA fluorescent probes based on the mechanism of 2\u2212aza\u2212Cope rearrangement. FA\u22122, in which a fluorophore is connected to a 4\u2212nitrobenzylamine group and an allyl group, demonstrated the highest sensitivity, selectivity, and reaction kinetics. Furthermore, FA\u2212Lyso, derived from FA\u22122, has been successfully designed and applied to monitor exogenous and endogenous FA fluctuations in lysosomes of living cells.<\/jats:p>","DOI":"10.3390\/bios12100855","type":"journal-article","created":{"date-parts":[[2022,10,10]],"date-time":"2022-10-10T21:07:11Z","timestamp":1665436031000},"page":"855","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Systematic Screening of Trigger Moieties for Designing Formaldehyde Fluorescent Probes and Application in Live Cell Imaging"],"prefix":"10.3390","volume":"12","author":[{"given":"Yin","family":"Jiang","sequence":"first","affiliation":[{"name":"School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, China"},{"name":"School of Biomedical and Pharmaceutical Sciences, Guangdong University of Technology, Guangzhou 510006, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shumei","family":"Huang","sequence":"additional","affiliation":[{"name":"School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, China"},{"name":"School of Biomedical and Pharmaceutical Sciences, Guangdong University of Technology, Guangzhou 510006, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Minghui","family":"Liu","sequence":"additional","affiliation":[{"name":"School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, China"},{"name":"School of Biomedical and Pharmaceutical Sciences, Guangdong University of Technology, Guangzhou 510006, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zejun","family":"Li","sequence":"additional","affiliation":[{"name":"School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, China"},{"name":"School of Biomedical and Pharmaceutical Sciences, Guangdong University of Technology, Guangzhou 510006, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Weimin","family":"Xiao","sequence":"additional","affiliation":[{"name":"Shenzhen Academy of Metrology & Quality Inspection, Shenzhen 518110, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Huatang","family":"Zhang","sequence":"additional","affiliation":[{"name":"School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, China"},{"name":"School of Biomedical and Pharmaceutical Sciences, Guangdong University of Technology, Guangzhou 510006, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Liu","family":"Yang","sequence":"additional","affiliation":[{"name":"College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hongyan","family":"Sun","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Center of Super-Diamond and Advanced Films (COSDAF), City University of Hong Kong, 83 Tat Chee Avenue, Kowloon, Hong Kong 999077, China"},{"name":"Key Laboratory of Biochip Technology, Biotech and Health Centre, Shenzhen Research Institute of City University of Hong Kong, Shenzhen 518057, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,10,10]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"2347","DOI":"10.1039\/C6GC03093A","article-title":"Future perspectives for formaldehyde: Pathways for reductive synthesis and energy storage","volume":"19","author":"Heim","year":"2017","journal-title":"Green Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"103134","DOI":"10.1016\/j.dnarep.2021.103134","article-title":"Perspectives on formaldehyde dysregulation: Mitochondrial DNA damage and repair in mammalian cells","volume":"105","author":"Nadalutti","year":"2021","journal-title":"DNA Repair"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"583","DOI":"10.1007\/s11357-012-9388-8","article-title":"Accumulated hippocampal formaldehyde induces age\u2212dependent memory decline","volume":"35","author":"Tong","year":"2013","journal-title":"Age"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"5578","DOI":"10.1038\/s41380-020-00929-7","article-title":"Degradation of FA reduces A\u03b2 neurotoxicity and Alzheimer\u2212related phenotypes","volume":"26","author":"Fei","year":"2021","journal-title":"Mol. Psychiatry"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"3669","DOI":"10.1096\/fj.201701239R","article-title":"Formaldehyde induces diabetes\u2212associated cognitive impairments","volume":"32","author":"Tan","year":"2018","journal-title":"FASEB J."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"313","DOI":"10.1289\/ehp.0901143","article-title":"Formaldehyde exposure and asthma in children: A systematic review","volume":"118","author":"McGwin","year":"2010","journal-title":"Environ. Health Perspect."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"177","DOI":"10.1016\/j.molcel.2015.08.020","article-title":"Endogenous Formaldehyde Is a Hematopoietic Stem Cell Genotoxin and Metabolic Carcinogen","volume":"60","author":"Pontel","year":"2015","journal-title":"Mol. Cell"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"3899","DOI":"10.1016\/j.cclet.2021.06.033","article-title":"NCL\u2212based mitochondrial\u2212targeting fluorescent probe for the detection of Glutathione in living cells","volume":"32","author":"Jin","year":"2021","journal-title":"Chin. Chem. Lett."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"2903","DOI":"10.1016\/j.cclet.2020.03.063","article-title":"Two\u2212photon dual\u2212channel fluorogenic probe for in situ imaging the mitochondrial H2S\/viscosity in the brain of drosophila Parkinson\u2019s disease model","volume":"31","author":"Fang","year":"2020","journal-title":"Chin. Chem. Lett."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"2945","DOI":"10.1016\/j.cclet.2020.05.038","article-title":"Sensing cytochrome P450 1A1 activity by a resorufin\u2212based isoform\u2212specific fluorescent probe","volume":"31","author":"Jin","year":"2020","journal-title":"Chin. Chem. Lett."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"2970","DOI":"10.1016\/j.cclet.2020.07.001","article-title":"Rearrangement regulated cysteine fluorescent probe for cellular oxidative stress evaluation induced by copper(II)","volume":"31","author":"Zhou","year":"2020","journal-title":"Chin. Chem. Lett."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"129","DOI":"10.1016\/j.cclet.2019.04.021","article-title":"Coumarinocoumarin\u2212based fluorescent probe for the sensitive and selective detection of hydrazine in living cells and zebra fish","volume":"31","author":"Fang","year":"2020","journal-title":"Chin. Chem. Lett."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"213","DOI":"10.1016\/j.cclet.2021.06.056","article-title":"A reversible microarray immobilization strategy based on thiol\u2212quinone reaction","volume":"33","author":"Feng","year":"2022","journal-title":"Chin. Chem. Lett."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1147","DOI":"10.1016\/j.cclet.2018.05.031","article-title":"A proximity\u2212induced covalent fluorescent probe for selective detection of bromodomain 4","volume":"29","author":"Feng","year":"2018","journal-title":"Chin. Chem. Lett."},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"Noor Aini, B., Siddiquee, S., and Ampon, K. (2016). Development of formaldehyde biosensor for determination of formalin in fish samples; malabar red snapper (Lutjanus malabaricus) and longtail tuna (Thunnus tonggol). Biosensors, 6.","DOI":"10.3390\/bios6030032"},{"key":"ref_16","doi-asserted-by":"crossref","unstructured":"Lyu, J., Wang, C., and Zhang, X. (2022). Rational Construction of a mitochondria\u2212targeted reversible fluorescent probe with intramolecular FRET for ratiometric monitoring sulfur dioxide and formaldehyde. Biosensors, 12.","DOI":"10.3390\/bios12090715"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"10886","DOI":"10.1021\/jacs.5b05340","article-title":"An aza\u2212Cope reactivity\u2212based fluorescent probe for imaging formaldehyde in living cells","volume":"137","author":"Brewer","year":"2015","journal-title":"J. Am. Chem. Soc."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"10890","DOI":"10.1021\/jacs.5b05339","article-title":"A reaction\u2212based fluorescent probe for imaging of formaldehyde in living cells","volume":"137","author":"Roth","year":"2015","journal-title":"J. Am. Chem. Soc."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"4913","DOI":"10.1016\/j.tetlet.2012.06.117","article-title":"A tailor designed fluorescent \u2018turn\u2212on\u2019 sensor of formaldehyde based on the BODIPY motif","volume":"53","author":"Song","year":"2012","journal-title":"Tetrahedron Lett."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"3356","DOI":"10.1002\/anie.201510373","article-title":"Development of a two\u2212photon fluorescent probe for imaging of endogenous formaldehyde in living tissues","volume":"55","author":"Tang","year":"2016","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"3871","DOI":"10.1039\/D0CC00676A","article-title":"Imaging of formaldehyde fluxes in epileptic brains with a two\u2212photon fluorescence probe","volume":"56","author":"Chen","year":"2020","journal-title":"Chem. Commun."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"4029","DOI":"10.1039\/C5CC09796G","article-title":"A ratiometric fluorescent formaldehyde probe for bioimaging applications","volume":"52","author":"He","year":"2016","journal-title":"Chem. Commun."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"13857","DOI":"10.1039\/D1SC04387K","article-title":"Systematic investigation of the aza\u2212Cope reaction for fluorescence imaging of formaldehyde in vitro and in vivo","volume":"12","author":"Du","year":"2021","journal-title":"Chem. Sci."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"16352","DOI":"10.1002\/anie.202001425","article-title":"Activity\u2212based genetically encoded fluorescent and luminescent probes for detecting formaldehyde in living cells","volume":"59","author":"Zhang","year":"2020","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1442","DOI":"10.1039\/D1CC05644A","article-title":"Reaction\u2212based fluorescent and chemiluminescent probes for formaldehyde detection and imaging","volume":"58","author":"Huang","year":"2022","journal-title":"Chem. Commun."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1935","DOI":"10.1016\/j.cclet.2017.07.018","article-title":"Recent advances in formaldehyde\u2212responsive fluorescent probes","volume":"28","author":"Xu","year":"2017","journal-title":"Chin. Chem. Lett."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"759","DOI":"10.1016\/j.cclet.2019.09.021","article-title":"Red carbon dots as label\u2212free two\u2212photon fluorescent nanoprobes for imaging of formaldehyde in living cells and zebrafishes","volume":"31","author":"Wang","year":"2020","journal-title":"Chin. Chem. Lett."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"3724","DOI":"10.1021\/acs.analchem.7b00044","article-title":"Ratiometric imaging of tissue by two\u2212photon microscopy: Observation of a high level of formaldehyde around mouse intestinal crypts","volume":"89","author":"Singha","year":"2017","journal-title":"Anal. Chem."},{"key":"ref_29","first-page":"3549","article-title":"Adducts of triallylborane with ammonia and aliphatic amines as stoichiometric allylating agents for aminoallylation reaction of carbonyl compounds, Org","volume":"20","author":"Kuznetsov","year":"2018","journal-title":"Lett."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"118073","DOI":"10.1016\/j.saa.2020.118073","article-title":"AND logic gate based fluorescence probe for simultaneous detection of peroxynitrite and hypochlorous acid, Spectrochim","volume":"230","author":"Li","year":"2020","journal-title":"Acta A Mol. Biomol. Spectrosc."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"10629","DOI":"10.1021\/ja203521e","article-title":"Development of a highly sensitive fluorescence probe for hydrogen peroxide, J","volume":"133","author":"Abo","year":"2011","journal-title":"Am. Chem. Soc."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"127890","DOI":"10.1016\/j.snb.2020.127890","article-title":"Two quenching groups are better than one: A robust strategy for constructing HOCl fluorescent probe with minimized background fluorescence and ultra\u2212high sensitivity and its application of HOCl imaging in living cells and tissues, Sens","volume":"310","author":"Zheng","year":"2020","journal-title":"Actuators B Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"3395","DOI":"10.1039\/C6AN00473C","article-title":"A two\u2212photon fluorescent probe for bio\u2212imaging of formaldehyde in living cells and tissues","volume":"141","author":"Li","year":"2016","journal-title":"Analyst"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"7851","DOI":"10.1039\/C7SC03719H","article-title":"Bright and sensitive ratiometric fluorescent probe enabling endogenous FA imaging and mechanistic exploration of indirect oxidative damage due to FA in various living systems","volume":"8","author":"Dou","year":"2017","journal-title":"Chem. Sci."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"6377","DOI":"10.1039\/C9NR00039A","article-title":"A ratiometric fluorescent nanoprobe based on naphthalimide derivative\u2212functionalized carbon dots for imaging lysosomal formaldehyde in HeLa cells","volume":"11","author":"Chen","year":"2019","journal-title":"Nanoscale"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"581","DOI":"10.1038\/s41467-020-20754-4","article-title":"Genetically encoded formaldehyde sensors inspired by a protein intra\u2212helical crosslinking reaction","volume":"12","author":"Zhu","year":"2021","journal-title":"Nat. Commun."}],"container-title":["Biosensors"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2079-6374\/12\/10\/855\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T00:49:07Z","timestamp":1760143747000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2079-6374\/12\/10\/855"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,10,10]]},"references-count":36,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2022,10]]}},"alternative-id":["bios12100855"],"URL":"https:\/\/doi.org\/10.3390\/bios12100855","relation":{},"ISSN":["2079-6374"],"issn-type":[{"value":"2079-6374","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,10,10]]}}}