{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,15]],"date-time":"2026-09-15T11:15:42Z","timestamp":1789470942956,"version":"build-2803163510"},"reference-count":32,"publisher":"MDPI AG","issue":"2","license":[{"start":{"date-parts":[[2013,2,18]],"date-time":"2013-02-18T00:00:00Z","timestamp":1361145600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Although they are widely used as insecticides, acaricides and fungicides in the agriculture or as raw materials in the dye industry, dinitrophenols (DNPs) are extremely noxious, death cases having been registered. These compounds produce cataracts, lower leucocyte levels, disturb the general metabolism and can cause cancer. It is also assumed that DNPs hinder the proton translocation through the mitochondrial inner membrane and therefore inhibit oxidative phosphorylation. Their fluorescence quenching properties can help understand and explain their toxicity. Fluorescence quenching of tryptophan was tested using different dinitrophenols such as 2,4-dinitrophenol (2,4-DNP), 4,6-dinitro-orthocresol (DNOC), 2-[(2,4-dinitrophenyl)amino]acetic acid (GlyDNP), 2-(1-methyl-heptyl)-4.6-dinitrophenyl crotonate (Karathan), 2-amino-5-[(1-((carboxymethyl)amino)-3-((2,4-dinitrophenyl)thio)-1-oxopropan-2-yl)amino]-5-oxopentanoic acid (SDN GSH),  2,4-dinitroanisole (2,4-DNA) and 2,4-dinitrobenzoic acid (2,4-DNB). 2,4-DNP and DNOC showed the highest tryptophan fluorescence quenching constant values, these being also the most toxic compounds. The electronic chemical potential value of the most stable complex of 2,4-DNP-with tryptophan is higher than the values of the electronic chemical potentials of complexes corresponding to the derivatives.<\/jats:p>","DOI":"10.3390\/molecules18022266","type":"journal-article","created":{"date-parts":[[2013,2,19]],"date-time":"2013-02-19T11:11:16Z","timestamp":1361272276000},"page":"2266-2280","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["Quenching of Tryptophan Fluorescence in the Presence of  2,4-DNP, 2,6-DNP, 2,4-DNA and DNOC and Their Mechanism  of Toxicity"],"prefix":"10.3390","volume":"18","author":[{"given":"Cristina-Amalia","family":"Dumitra\u015f Hu\u0163anu","sequence":"first","affiliation":[{"name":"Faculty of Chemistry, \"Al. I. Cuza\" University, 11 Carol I, RO-700506 Iasi, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marius","family":"Zaharia","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, \"Al. I. Cuza\" University, 11 Carol I, RO-700506 Iasi, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Olga","family":"Pintilie","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, \"Al. I. Cuza\" University, 11 Carol I, RO-700506 Iasi, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2013,2,18]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1007\/s12640-009-9133-y","article-title":"Expression profile of rat hippocampal neurons treated with the neuroprotective compound 2,4-dinitrophenol: Up-regulation of cAMP signaling genes","volume":"18","author":"Sebollela","year":"2009","journal-title":"Neurotox. Res."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"3427","DOI":"10.1021\/ac300306p","article-title":"Fast separation and quantification method for nitroguanidine and 2,4-dinitroanisole by ultrafast liquid chromatography-tandem mass spectrometry","volume":"84","author":"Mu","year":"2012","journal-title":"Anal. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"247","DOI":"10.1016\/S0890-6238(02)00130-2","article-title":"Effects of dinoseb, 4,6-dinitro-o-cresol, and 2,4-dinitrophenol on rat Sertoli-germ cell co-cultures","volume":"17","author":"Takahashi","year":"2003","journal-title":"Reprod. Toxicol."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1108","DOI":"10.1095\/biolreprod.104.028639","article-title":"Oxygen-regulated gene expression in bovine blastocysts","volume":"71","author":"Harvey","year":"2004","journal-title":"Biol. Reprod."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"247","DOI":"10.1080\/10659360500036703","article-title":"Assessment of baseline toxicity of mono-cyclic aromatic compounds by pseudomonas initial oxygen uptake assay","volume":"16","author":"Wang","year":"2005","journal-title":"SAR QSAR Environ. Res."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"597","DOI":"10.1071\/RD05064","article-title":"Metabolic regulation of in vitro-produced bovine embryos. II. Effects of phenazine ethosulfate, sodium azide and 2,4-dinitrophenol during post-compaction development on glucose metabolism and lipid accumulation","volume":"18","author":"Gardner","year":"2006","journal-title":"Reprod. Fertil. Dev."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"255","DOI":"10.1046\/j.1467-789X.2001.00043.x","article-title":"Mitochondrial uncoupling as a target for drug development for the treatment of obesity","volume":"2","author":"Harper","year":"2001","journal-title":"Obes. Rev."},{"key":"ref_8","first-page":"683","article-title":"Dinitrophenol oral ingestion resulting death","volume":"40","author":"Pace","year":"2002","journal-title":"Clin. Toxicol."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"157","DOI":"10.1016\/j.bej.2005.03.018","article-title":"Degradation of 2,4-dichlorophenol by mixed culture of photoautotrophic microorganisms","volume":"29","author":"Hirooka","year":"2006","journal-title":"Biochem. Eng. J."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1676","DOI":"10.1111\/j.1471-4159.2005.03328.x","article-title":"The mitochondrial uncoupler 2,4-dinitrophenol attenuates tissue damage and improves mitochondrial homeostasis following transient focal cerebral ischemia","volume":"94","author":"Korde","year":"2005","journal-title":"J. Neurochem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"263","DOI":"10.2174\/156720507781077287","article-title":"Cyclic AMP enhancers and Abeta oligomerization blockers as potential therapeutic agents in Alzheimer\u2019s disease","volume":"4","author":"Barbarosa","year":"2007","journal-title":"Curr. Alzheimer Res."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"659","DOI":"10.1016\/j.tiv.2007.12.005","article-title":"2,4-dinitrophenol induces G1 phase arrest and apoptosis in human pulmonary adenocarcinoma Calu-6 cells","volume":"22","author":"Han","year":"2008","journal-title":"Toxicol. In Vitro"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"3540","DOI":"10.1016\/j.fct.2008.09.005","article-title":"Analysis of cyanogens with resorcinol and picrate","volume":"46","author":"Drochioiu","year":"2008","journal-title":"Food Chem. Toxicol."},{"key":"ref_14","first-page":"4393","article-title":"Biological effect and the Toxicity mechanisms of some dinitrophenyl ethers","volume":"6","author":"Pui","year":"2009","journal-title":"Rom. Biotechnol. Lett."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"573","DOI":"10.1089\/pho.2009.2651","article-title":"Laser-induced ATP formation: Mechanism and consequences","volume":"28","author":"Drochioiu","year":"2010","journal-title":"Photomed. Laser Surg."},{"key":"ref_16","unstructured":"Mitchell, P. (Nobel Lecture, 1978). David Keilin\u2019s respiratory chain concept and its chemiosmotic consequences, Nobel Lecture."},{"key":"ref_17","first-page":"1579","article-title":"The biostructural theory versus the chemiosmotic theory","volume":"9","author":"Drochioiu","year":"2004","journal-title":"Roum. Biotechnol. Lett."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"873","DOI":"10.1126\/science.124.3227.873","article-title":"Bioenergetics","volume":"124","year":"1956","journal-title":"Science"},{"key":"ref_19","first-page":"9","article-title":"Effect of Dinitrophenol Pesticides and Dinitrophenyl Derivatives on Germination of Wheat Seeds U.S.A.M.V","volume":"52","author":"Drochioiu","year":"2009","journal-title":"Horticulture Series"},{"key":"ref_20","first-page":"73","article-title":"Dinitrophenyl derivatives action on wheat germination","volume":"14","year":"2010","journal-title":"Ovidius University Annals Biology-Ecology Series"},{"key":"ref_21","first-page":"130","article-title":"Quenching of tryptophan and 4,4\u2032-diaminostilbene fluorescence by dinitrophenyl ethers: Use of 1-allyloxy-2,4-dinitrobenzene, as a quencher","volume":"16","author":"Rusu","year":"2011","journal-title":"Rom. Biotechnol. Lett."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1442","DOI":"10.1096\/fj.11-199869","article-title":"Glutathione-dependent reductive stress triggers mitochondrial oxidation and cytotoxicity","volume":"26","author":"Zhang","year":"2012","journal-title":"FASEB J."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"458","DOI":"10.1007\/s10953-011-9664-8","article-title":"Study on the Interaction of pentachlorophenol with Urease in Aqueous Solution by Multiple Spectroscopic Techniques","volume":"40","author":"Wang","year":"2011","journal-title":"J. Solution Chem."},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Lakowicz, J.R. (1999). Principles of Fluorescence Spectroscopy, Kluwer Academic\/Plenum Publishers. [2nd].","DOI":"10.1007\/978-1-4757-3061-6"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"247","DOI":"10.1016\/j.saa.2007.07.054","article-title":"Fluorescence quenching of CdSe quantum dots bynitroaromatic explosives and their relative compounds","volume":"70","author":"Shi","year":"2008","journal-title":"Spectrochim. Acta Part A"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1391","DOI":"10.1110\/ps.03508204","article-title":"Distinct conformational stability and functional activity of four highly homologous endonuclease colicins","volume":"13","author":"Spelbrink","year":"2004","journal-title":"Protein Sci."},{"key":"ref_27","unstructured":"Dumitra\u015f-Hu\u0163anu, C.A., Gradinaru, R.V., Maftei, D., and Drochioiu, G. (2011). Days of \u201cAl. I. Cuza\u201d University."},{"key":"ref_28","unstructured":"Cordos, E., Frentiu, T., Ponta, M., and Darvasi, E. (2001). Analiza prin spectrometrie de absorb\u0163ie moleculara \u00een ultraviolet-vizibil, Istitutul Na\u0163ional de Optoelectronic\u0103."},{"key":"ref_29","first-page":"210","article-title":"Lipophilicity of few chromen-2-ones and chromene-2-thiones by Hyperchem 7.0 AND Alogps 2.1","volume":"2","author":"Jayanthi","year":"2011","journal-title":"Pharm. Sci. Monitor"},{"key":"ref_30","unstructured":"N\u0103dejde, C. (2010). Spectral investigation of solutions intermolecular interactions in organic compounds of biological interest. [PhD thesis, \u201cAl. I. Cuza\u201d University]."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"369","DOI":"10.1007\/BF02708340","article-title":"Chemical hardness and density functional theory","volume":"117","author":"Pearson","year":"2005","journal-title":"J. Chem. Sci."},{"key":"ref_32","unstructured":"Snedecor, G.W. (1994). Statistical Methods Applied to Experiments in Agriculture and Biology, The Iowa Stat Univ. Press."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/18\/2\/2266\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T21:45:00Z","timestamp":1760219100000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/18\/2\/2266"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,2,18]]},"references-count":32,"journal-issue":{"issue":"2","published-online":{"date-parts":[[2013,2]]}},"alternative-id":["molecules18022266"],"URL":"https:\/\/doi.org\/10.3390\/molecules18022266","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2013,2,18]]}}}