Summary: Derivatives of CRESOLS containing two nitro groups.

Top Publications

  1. Pu Y, Wang W, Yang Y, Alfano R. Native fluorescence spectra of human cancerous and normal breast tissues analyzed with non-negative constraint methods. Appl Opt. 2013;52:1293-301 pubmed publisher
    ..Native fluorescence spectroscopy analyzed by MCR-ALS may have the potential to be a new armamentarium. ..
  2. Adak S, Begley T. RutA-Catalyzed Oxidative Cleavage of the Uracil Amide Involves Formation of a Flavin-N5-oxide. Biochemistry. 2017;56:3708-3709 pubmed publisher
    ..RutA is a novel flavoenzyme on the uracil catabolic pathway that catalyzes uracil ring opening by a unique amide oxidation reaction. Here we provide evidence that this reaction also involves the formation of a flavin-N5-oxide...
  3. Braunbeck T, Volkl A. Induction of biotransformation in the liver of Eel (Anguilla anguilla L.) by sublethal exposure to dinitro-o-cresol: an ultrastructural and biochemical study. Ecotoxicol Environ Saf. 1991;21:109-27 pubmed
    ..Comparison of DNOC-induced effects with liver pathology in eel exposed to the chemical spill in 1986 reveals striking similarities so that DNOC may not be excluded as a possible factor in the fish kill in the Rhine river. ..
  4. Morrison J, John G. The non-enzymatic reduction of azo dyes by flavin and nicotinamide cofactors under varying conditions. Anaerobe. 2013;23:87-96 pubmed publisher
    ..This study details the importance of the use of a cofactor-only control when studying azoreductase enzymes. ..
  5. Rui Z, Sandy M, Jung B, Zhang W. Tandem enzymatic oxygenations in biosynthesis of epoxyquinone pharmacophore of manumycin-type metabolites. Chem Biol. 2013;20:879-87 pubmed publisher
    ..We further demonstrate that the epoxyquinone moiety is critical for anti-MRSA activity by analyzing the bioactivity of various manumycin-type metabolites produced through mutasynthesis. ..
  6. Sun Y, Pu Y, Yang Y, Alfano R. Biomarkers spectral subspace for cancer detection. J Biomed Opt. 2012;17:107005 pubmed publisher
    ..Second, the efficacy of biomarkers in cancer detection can be determined. ..
  7. Tuxen N, Tüchsen P, Rugge K, Albrechtsen H, Bjerg P. Fate of seven pesticides in an aerobic aquifer studied in column experiments. Chemosphere. 2000;41:1485-94 pubmed
    ..After lag periods of 16-33 days for the phenoxy acids and 80 days for DNOC, these pesticides were degraded quickly with 0.-order rate constants of 1.3-2.6 microg/l/day. None of the most probable degradation products were detected. ..
  8. Huţanu C, 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;18:2266-80 pubmed publisher
    ..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. ..
  9. Marlin F, Simon P, Bonneau S, Alberti P, Cordier C, Boix C, et al. Flavin conjugates for delivery of peptide nucleic acids. Chembiochem. 2012;13:2593-8 pubmed publisher
    ..Our findings could be useful for further design of PNAs and other oligonucleotide analogues as potent antisense agents. ..

More Information


  1. Romero E, Fedkenheuer M, Chocklett S, Qi J, Oppenheimer M, Sobrado P. Dual role of NADP(H) in the reaction of a flavin dependent N-hydroxylating monooxygenase. Biochim Biophys Acta. 2012;1824:850-7 pubmed publisher
    ..Together, these results are consistent with NADPH having a role in flavin reduction and in the modulation of conformational changes, which positions NADP(+) to also play a role in stabilization of the C4a-hydroperoxyflavin. ..
  2. Takahashi K, Hojo H, Aoyama H, Teramoto S. Comparative studies on the spermatotoxic effects of dinoseb and its structurally related chemicals. Reprod Toxicol. 2004;18:581-8 pubmed
    ..DNP also caused slightly increased incidence of tailless sperm on D14. These results demonstrate that DNBP, DNOC, and DNP manifest similar spermatotoxic effects at or around a lethal dose in rats. ..
  3. Johnston C, De Oliveira M, Teppen B, Sheng G, Boyd S. Spectroscopic study of nitroaromatic-smectite sorption mechanisms. Environ Sci Technol. 2001;35:4767-72 pubmed
    ..Results indicate that the sorption of NACs to smectite surfaces is controlled largely by the hydration characteristics of the exchangeable cation, which regulates both cation-nitroaromatic complexation and swelling of the smectite. ..
  4. Johnston C, Sheng G, Teppen B, Boyd S, De Oliveira M. Spectroscopic study of dinitrophenol herbicide sorption on smectite. Environ Sci Technol. 2002;36:5067-74 pubmed
    ..These two observations (sorption isotherms and molar absorptivity) provide a direct link between the macroscopic sorption results and the FTIR spectra. ..
  5. Gujar M, Stricker A, Lundquist E. Flavin monooxygenases regulate Caenorhabditis elegans axon guidance and growth cone protrusion with UNC-6/Netrin signaling and Rac GTPases. PLoS Genet. 2017;13:e1006998 pubmed publisher
    ..From these studies we conclude that FMO-1, FMO-4, FMO-5, and EHBP-1 represent new players downstream of UNC-6/Netrin receptors and Rac GTPases that inhibit growth cone filopodial protrusion in repulsive axon guidance. ..
  6. Kane A, Bond D, Gralnick J. Electrochemical analysis of Shewanella oneidensis engineered to bind gold electrodes. ACS Synth Biol. 2013;2:93-101 pubmed publisher
    ..This study provides a strategy to specifically immobilize bacteria to electrodes while also outlining challenges involved in merging synthetic biology approaches with native cellular pathways and cell surface charge...
  7. Takahashi K, Aoyama H, Kawashima K, Teramoto S. Effects of dinoseb, 4,6-dinitro-o-cresol, and 2,4-dinitrophenol on rat Sertoli-germ cell co-cultures. Reprod Toxicol. 2003;17:247-52 pubmed
    ..These results demonstrate that DNBP, DNOC, and DNP have in vitro toxicity to these cell populations at high concentration, and suggest the possibility that DNOC and DNP also cause testicular damage in experimental animals and humans. ..
  8. Grilli S, Ancora G, Rani P, Valenti A, Mazzullo M, Colacci A. In vivo unwinding fluorimetric assay as evidence of the damage induced by fenarimol and DNOC in rat liver DNA. J Toxicol Environ Health. 1991;34:485-94 pubmed
    ..Two pesticides, fenarimol and DNOC, were capable of inducing DNA damage because they significantly increased the DNA unwinding rate. On the contrary, amitraz, cyanazine, and cyhexatin were not DNA-damaging agents. ..
  9. Gisi D, Stucki G, Hanselmann K. Biodegradation of the pesticide 4,6-dinitro-ortho-cresol by microorganisms in batch cultures and in fixed-bed column reactors. Appl Microbiol Biotechnol. 1997;48:441-8 pubmed
    ..Degradation was inhibited at DNOC concentrations above 30 microM and it ceased at 340 microM, possibly because of the uncoupling action of the nitroaromatic compound on the cellular energy-transducing mechanism. ..
  10. Miskiniene V, Sarlauskas J, Jacquot J, Cenas N. Nitroreductase reactions of Arabidopsis thaliana thioredoxin reductase. Biochim Biophys Acta. 1998;1366:275-83 pubmed
    ..Our data indicate that certain nitroaromatic herbicides, explosives and other classes of xenobiotics may interfere with the reduction of thioredoxin by plant TR, and confer prooxidant properties to this antioxidant enzyme. ..
  11. Sobrado P, Tanner J. Multiple functionalities of reduced flavin in the non-redox reaction catalyzed by UDP-galactopyranose mutase. Arch Biochem Biophys. 2017;632:59-65 pubmed publisher
    ..Recent results from mechanistic enzymology, kinetic crystallography, and computational chemistry provide a complete picture of the chemical mechanism of UDP-galactopyranose mutase. ..
  12. Freddolino P, Gardner K, Schulten K. Signaling mechanisms of LOV domains: new insights from molecular dynamics studies. Photochem Photobiol Sci. 2013;12:1158-70 pubmed publisher
  13. Nisar M, Rashid N, Bashir Q, Gardner Q, Shafiq M, Akhtar M. TK1299, a highly thermostable NAD(P)H oxidase from Thermococcus kodakaraensis exhibiting higher enzymatic activity with NADPH. J Biosci Bioeng. 2013;116:39-44 pubmed publisher
    ..To our knowledge this is the most thermostable and unique NAD(P)H oxidase displaying higher enzyme activity with NADPH. ..
  14. Ashauer R, Hintermeister A, Potthoff E, Escher B. Acute toxicity of organic chemicals to Gammarus pulex correlates with sensitivity of Daphnia magna across most modes of action. Aquat Toxicol. 2011;103:38-45 pubmed publisher
    ..Thus, G. pulex is generally equally sensitive towards organic xenobiotics as D. magna...
  15. Meints C, Simtchouk S, Wolthers K. Aromatic substitution of the FAD-shielding tryptophan reveals its differential role in regulating electron flux in methionine synthase reductase and cytochrome P450 reductase. FEBS J. 2013;280:1460-74 pubmed publisher
    ..By contrast, the bulky indole ring of W676 accelerates catalysis in CPR by lowering the energy barrier for displacement of the oxidized nicotinamide ring coplanar with the FAD. ..
  16. Castilho R, Vicente J, Kowaltowski A, Vercesi A. 4,6-Dinitro-o-cresol uncouples oxidative phosphorylation and induces membrane permeability transition in rat liver mitochondria. Int J Biochem Cell Biol. 1997;29:1005-11 pubmed
    ..Treatment of Ca(2+)-loaded mitochondria with uncoupling concentrations of DNOC results in mitochondrial permeability transition, associated with membrane protein thiol oxidation by reactive oxygen species. ..
  17. Cheng V, Tran Q, Boroumand N, Rothery R, Maklashina E, Cecchini G, et al. A conserved lysine residue controls iron-sulfur cluster redox chemistry in Escherichia coli fumarate reductase. Biochim Biophys Acta. 2013;1827:1141-7 pubmed publisher
    ..Although this residue is absolutely conserved, they have diverged to achieve different functions in Frd and Sdh. ..
  18. Wang H, Wang H, Jiang W. Solar photocatalytic degradation of 2,6-dinitro-p-cresol (DNPC) using multi-walled carbon nanotubes (MWCNTs)-TiO(2) composite photocatalysts. Chemosphere. 2009;75:1105-11 pubmed publisher
    ..The results of the study showed the feasible and potential use of MWCNTs-TiO(2) composite in degradation of toxic organic pollutants. ..
  19. Chorvatova A, Aneba S, Mateasik A, Chorvat D, Comte B. Time-resolved fluorescence spectroscopy investigation of the effect of 4-hydroxynonenal on endogenous NAD(P)H in living cardiac myocytes. J Biomed Opt. 2013;18:067009 pubmed publisher
    ..Understanding the precise role of oxidative processes and their products in living cells is crucial for finding new noninvasive tools for biomedical diagnostics of pathophysiological states. ..
  20. Ghillebaert F, Chaillou C, Deschamps F, Roubaud P. Toxic effects, at three pH levels, of two reference molecules on common carp embryo. Ecotoxicol Environ Saf. 1995;32:19-28 pubmed
    ..The toxicological interpretation of these results is discussed. They confirm the need of multifactorial methods for toxic risks and effects assessment on fish early life stages in the environment. ..
  21. Hrelia P, Vigagni F, Maffei F, Morotti M, Colacci A, Perocco P, et al. Genetic safety evaluation of pesticides in different short-term tests. Mutat Res. 1994;321:219-28 pubmed
    ..The results provide further information on the intrinsic genotoxic activity of the tested pesticides, which may contribute to the toxicological assessment of the risk associated with human exposure. ..
  22. Birrell J, Morina K, Bridges H, Friedrich T, Hirst J. Investigating the function of [2Fe-2S] cluster N1a, the off-pathway cluster in complex I, by manipulating its reduction potential. Biochem J. 2013;456:139-46 pubmed publisher
    ..lipolytica complex I, but N1a was still not reduced by NADH. We conclude that cluster N1a does not affect reactive oxygen species production by the complex I flavin; it is probably required for enzyme assembly or stability. ..
  23. Amariei C, Machné R, Sasidharan K, Gottstein W, Tomita M, Soga T, et al. The dynamics of cellular energetics during continuous yeast culture. Conf Proc IEEE Eng Med Biol Soc. 2013;2013:2708-11 pubmed publisher
    ..Ultimately, this leads to a global partitioning of anabolism and catabolism and the enzymes involved, mediated by a relatively simple ATP feedback loop on chromatin architecture. ..
  24. Tanvir S, Thuroczy G, Selmaoui B, Silva Pires Antonietti V, Sonnet P, Arnaud Cormos D, et al. Effects of 3G cell phone exposure on the structure and function of the human cytochrome P450 reductase. Bioelectrochemistry. 2016;111:62-9 pubmed publisher
    ..This change was due to small changes in the tertiary and secondary structures of the protein at 37°C. The relevance of these findings to an actual RF exposure scenario demands further biochemical and in-vivo confirmation. ..
  25. Arildskov N, Pedersen P, Albrechtsen H. Fate of the herbicides 2,4,5-T, atrazine, and DNOC in a shallow, anaerobic aquifer investigated by in situ passive diffusive emitters and laboratory batch experiments. Ground Water. 2001;39:819-30 pubmed
    ..The DNOC degradation in the methanogenic incubations (8 to 9 mbs) was up to 50 times faster than in the sediments from 3 to 4 mbs, likely due to the low redox potential. ..
  26. Lee S, Lévesque S, Sevigny J, Muller C. A highly sensitive capillary electrophoresis method using p-nitrophenyl 5'-thymidine monophosphate as a substrate for the monitoring of nucleotide pyrophosphatase/phosphodiesterase activities. J Chromatogr B Analyt Technol Biomed Life Sci. 2012;911:162-9 pubmed publisher
    ..Therefore, this new method is an improvement of actual techniques and could be used as a quick and standard analytical technique for the identification and characterization of NPP inhibitors. ..
  27. Kruger S, Herzog M, Kuhlmey H, Werner E. [Circadian rhythm of the toxicokinetics and toxicodynamics of the plant protection substance dinitro-ortho-cresol in rabbits]. Dtsch Tierarztl Wochenschr. 1991;98:376-81 pubmed
    ..m., however it depends on the dose. The results are showing, that the position of acrophase by constant environmental factor is neither a substance specific nor an animal specific constant. ..
  28. Kotloski N, Gralnick J. Flavin electron shuttles dominate extracellular electron transfer by Shewanella oneidensis. MBio. 2013;4: pubmed publisher
    ..oneidensis. Analysis of a strain that is unable to secrete flavins demonstrated that electron shuttling accounts for ~75% of the insoluble extracellular electron transfer capacity in S. oneidensis. ..
  29. Rossner R, Kaeberlein M, Leiser S. Flavin-containing monooxygenases in aging and disease: Emerging roles for ancient enzymes. J Biol Chem. 2017;292:11138-11146 pubmed publisher
    ..Here, we present an overview of evidence for FMOs' involvement in aging and disease, discussing the biological context and arguing for increased investigation into the function of these enzymes. ..
  30. Takahashi K, Takahashi N, Hojo H, Kuwahara M, Aoyama H, Teramoto S. Pathogenetic transition in the morphology of abnormal sperm in the testes and the caput, corpus, and cauda epididymides of male rats after treatment with 4,6-dinitro-o-cresol. Reprod Toxicol. 2006;22:501-7 pubmed
  31. Heusinkveld H, van Vliet A, Nijssen P, Westerink R. In vitro neurotoxic hazard characterisation of dinitrophenolic herbicides. Toxicol Lett. 2016;252:62-9 pubmed publisher
    ..The combined results indicate that in vitro exposure to DNOC and dinoseb activates pathways that are not only involved in acute neurotoxicity but also in long-term effects as seen in neurodegeneration. ..
  32. Sjulstok E, Olsen J, Solov yov I. Quantifying electron transfer reactions in biological systems: what interactions play the major role?. Sci Rep. 2015;5:18446 pubmed publisher
  33. Robinson R, Rodríguez P, Sobrado P. Mechanistic studies on the flavin-dependent N?-lysine monooxygenase MbsG reveal an unusual control for catalysis. Arch Biochem Biophys. 2014;550-551:58-66 pubmed publisher
    ..Together, the results indicate a unique mechanism where a rate-limiting and pH-sensitive conformational change occurs in the reductive half-reaction, which affects the efficiency of lysine hydroxylation. ..
  34. Quinto I, De Marinis E, Mallardo M, Arcucci A, Della Morte R, Staiano N. Effect of DNOC, Ferbam and Imidan exposure on mouse sperm morphology. Mutat Res. 1989;224:405-8 pubmed
    ..w./day. These data indicate that per os administration of Ferbam succeeded in producing active metabolites able to interfere with the differentiation process of spermatogenic cells...
  35. Ye P, Lemley A. Adsorption effect on the degradation of 4,6-o-dinitrocresol and p-nitrophenol in a montmorillonite clay slurry by AFT. Water Res. 2009;43:1303-12 pubmed publisher
    ..Overall, the results showed the inhibition effect of adsorption on the degradation of nitroaromatic compounds in montmorillonite clay slurry by AFT, providing important implications for water and soil remediation. ..
  36. Matsumoto M, Hirose A, Ema M. Review of testicular toxicity of dinitrophenolic compounds, 2-sec-butyl-4,6-dinitrophenol, 4,6-dinitro-o-cresol and 2,4-dinitrophenol. Reprod Toxicol. 2008;26:185-90 pubmed publisher
    ..Further studies in laboratory animals with nitrophenolic compounds are required for clarification of their testicular toxicity and for risk assessment in humans. ..
  37. Aranha M, Matos A, Teresa Mendes A, Vaz Pinto V, Rodrigues C, Arrabaça J. Dinitro-o-cresol induces apoptosis-like cell death but not alternative oxidase expression in soybean cells. J Plant Physiol. 2007;164:675-84 pubmed
    ..Further, the role of AOX in cell death has not been confirmed, and may depend on the nature and intensity of stress conditions. ..
  38. Winkler C, Clay D, van Heerden E, Faber K. Overcoming co-product inhibition in the nicotinamide independent asymmetric bioreduction of activated C=C-bonds using flavin-dependent ene-reductases. Biotechnol Bioeng. 2013;110:3085-92 pubmed publisher
    ..The optimized system allowed to reduce an alkene activated by ester groups in a "coupled-substrate" approach via nicotinamide-free hydrogen transfer with >90% conversion and complete stereoselectivity. ..
  39. Martínez J, Frago S, Lans I, Alonso P, García Rubio I, Medina M. Spin Densities in Flavin Analogs within a Flavoprotein. Biophys J. 2016;110:561-571 pubmed publisher
    ..When these effects were analyzed together with the functional properties of the different flavodoxin variants, a relationship between spin population and biochemical parameters, as the reduction potential, could be envisaged. ..
  40. Zabala D, Cartwright J, Roberts D, Law B, Song L, Samborskyy M, et al. A Flavin-Dependent Decarboxylase-Dehydrogenase-Monooxygenase Assembles the Warhead of ?,?-Epoxyketone Proteasome Inhibitors. J Am Chem Soc. 2016;138:4342-5 pubmed publisher
    ..The biosynthesis of the TMC-86A warhead is completed by cytochrome P450-mediated hydroxylation of the ?-methyl-?,?-epoxyketone. ..
  41. Galeano Díaz T, Guiberteau Cabanillas A, Mora Diez N, Parrilla Vázquez P, Salinas López F. Rapid and sensitive determination of 4-nitrophenol, 3-methyl-4-nitrophenol, 4,6-dinitro-o-cresol, parathion-methyl, fenitrothion, and parathion-ethyl by liquid chromatography with electrochemical detection. J Agric Food Chem. 2000;48:4508-13 pubmed
    ..5 ppb in a river water sample, and their relative standard deviations were between 1 and 15%. The detection limits of these compounds ranged between 0.05 and 0.14 ppb. ..
  42. Broholm M, Tuxen N, Rugge K, Bjerg P. Sorption and degradation of the herbicide 2-methyl-4,6-dinitrophenol under aerobic conditions in a sandy aquifer in Vejen, Denmark. Environ Sci Technol. 2001;35:4789-97 pubmed
    ..This was supported by the laboratory experiments. The potential for natural attenuation of DNOC in aerobic aquifers appears promising. ..
  43. Nguyen Ngoc H, Durrieu C, Tran Minh C. Synchronous-scan fluorescence of algal cells for toxicity assessment of heavy metals and herbicides. Ecotoxicol Environ Saf. 2009;72:316-20 pubmed publisher
    ..The toxic effect of those chemicals mainly results in a quenching of algal cells fluorescence by reducing their photosynthetic activity...
  44. Zou Y, Zhang X, Su F, Liu X. Importance of riboflavin kinase in the pathogenesis of stroke. CNS Neurosci Ther. 2012;18:834-40 pubmed publisher
    ..RFK might act as a therapeutic target for stroke. ..
  45. Bieganska J. Neutralization of 4,6-dinitro-o-cresol waste pesticide by means of detonative combustion. Environ Sci Technol. 2005;39:1190-6 pubmed
    ..Biological tests with plants were carried out as well. Suggestion was made that the energy being produced during detonative combustion can be utilized for useful work, e.g. rock mining in a quarry. ..
  46. Elanskaya I, Chesnavichene E, Vernotte C, Astier C. Resistance to nitrophenolic herbicides and metronidazole in the cyanobacterium Synechocystis sp. PCC 6803 as a result of the inactivation of a nitroreductase-like protein encoded by drgA gene. FEBS Lett. 1998;428:188-92 pubmed
    ..Mutations blocking the activity of the DrgA protein lead to the development of resistance to nitrophenolic herbicides and metronidazole. ..
  47. Koziol L, Kumar N, Wong S, Lightstone F. Molecular recognition of aromatic rings by flavin: electrostatics and dispersion determine ring positioning above isoalloxazine. J Phys Chem A. 2013;117:12946-52 pubmed publisher
    ..The interplay of these interactions can be used to tune molecular recognition properties of synthetic redox cofactors, including positioning desired functional groups adjacent to the redox-active N5. ..
  48. Megarity C, Gill J, Caraher M, Stratford I, Nolan K, Timson D. The two common polymorphic forms of human NRH-quinone oxidoreductase 2 (NQO2) have different biochemical properties. FEBS Lett. 2014;588:1666-72 pubmed publisher
    ..Thus these data demonstrate, for the first time, clear biochemical differences between the variants which help explain previous biomedical and epidemiological findings. ..
  49. Zeng X, Lemley A. Fenton degradation of 4,6-dinitro-o-cresol with Fe(2+)-substituted ion-exchange resin. J Agric Food Chem. 2009;57:3689-94 pubmed publisher
    ..Degradation of DNOC under different delivery rates of H(2)O(2) was studied, and optimal conditions were determined. The results also showed that the delivery rate of H(2)O(2) did not affect the ion-exchange process of the resin. ..