Next Article in Journal
Enthalpy/Entropy Contributions to Conformational KIEs: Theoretical Predictions and Comparison with Experiment
Previous Article in Journal
Characterization of Proanthocyanidins in Stems of Polygonum multiflorum Thunb as Strong Starch Hydrolase Inhibitors
Molecules 2013, 18(2), 2266-2280; doi:10.3390/molecules18022266
Article

Quenching of Tryptophan Fluorescence in the Presence of 2,4-DNP, 2,6-DNP, 2,4-DNA and DNOC and Their Mechanism of Toxicity

* ,  and
Faculty of Chemistry, "Al. I. Cuza" University, 11 Carol I, RO-700506 Iasi, Romania
* Author to whom correspondence should be addressed.
Received: 4 January 2013 / Revised: 6 February 2013 / Accepted: 13 February 2013 / Published: 18 February 2013
Download PDF [493 KB, uploaded 18 June 2014]

Abstract

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.
Keywords: dinitrophenols; 2,4-dinitroanisole; oxidative phosphorylation; tryptophan; fluorescence; complex; computational; electronic chemical potential dinitrophenols; 2,4-dinitroanisole; oxidative phosphorylation; tryptophan; fluorescence; complex; computational; electronic chemical potential
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Export to BibTeX |
EndNote


MDPI and ACS Style

Dumitraş Huţanu, C.-A.; Zaharia, M.; Pintilie, O. Quenching of Tryptophan Fluorescence in the Presence of 2,4-DNP, 2,6-DNP, 2,4-DNA and DNOC and Their Mechanism of Toxicity. Molecules 2013, 18, 2266-2280.

View more citation formats

Related Articles

Article Metrics

Comments

Citing Articles

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert