carboxin

Summary

Summary: A systemic agricultural fungicide and seed treatment agent.

Top Publications

  1. Broomfield P, Hargreaves J. A single amino-acid change in the iron-sulphur protein subunit of succinate dehydrogenase confers resistance to carboxin in Ustilago maydis. Curr Genet. 1992;22:117-21 pubmed
    ..Ip) subunit of succinate dehydrogenase (Sdh) was determined following PCR amplification of genomic DNA from a carboxin (Cbx)-sensitive Ustilago maydis strain...
  2. Kilaru S, Collins C, Hartley A, Burns C, Foster G, Bailey A. Investigating dominant selection markers for Coprinopsis cinerea: a carboxin resistance system and re-evaluation of hygromycin and phleomycin resistance vectors. Curr Genet. 2009;55:543-50 pubmed publisher
    ..A carboxin resistance allele of the Coprinopsis cinerea sdi1 gene, encoding the iron-sulphur protein subunit of succinate ..
  3. Matsson M, Ackrell B, Cochran B, Hederstedt L. Carboxin resistance in Paracoccus denitrificans conferred by a mutation in the membrane-anchor domain of succinate:quinone reductase. Arch Microbiol. 1998;170:27-37 pubmed
    Succinate:quinone reductase is a membrane-bound enzyme of the citric acid cycle and the respiratory chain. Carboxin is a potent inhibitor of the enzyme of certain organisms...
  4. Huang L, Sun G, Cobessi D, Wang A, Shen J, Tung E, et al. 3-nitropropionic acid is a suicide inhibitor of mitochondrial respiration that, upon oxidation by complex II, forms a covalent adduct with a catalytic base arginine in the active site of the enzyme. J Biol Chem. 2006;281:5965-72 pubmed
  5. Shima Y, Ito Y, Kaneko S, Hatabayashi H, Watanabe Y, Adachi Y, et al. Identification of three mutant loci conferring carboxin-resistance and development of a novel transformation system in Aspergillus oryzae. Fungal Genet Biol. 2009;46:67-76 pubmed publisher
    Mutants exhibiting resistance to the fungicide, carboxin, were isolated from Aspergillus oryzae, and the mutations in the three gene loci, which encode succinate dehydrogenase (SDH) B, C, and D subunits, were identified to be ..
  6. Honda Y, Matsuyama T, Irie T, Watanabe T, Kuwahara M. Carboxin resistance transformation of the homobasidiomycete fungus Pleurotus ostreatus. Curr Genet. 2000;37:209-12 pubmed
    ..Ip subunit with an amino-acid substitution (His239 to Leu) and confers resistance to the systemic fungicide, carboxin. The DNA sequence was integrated ectopically in the chromosome of the transformants...
  7. Skinner W, Bailey A, Renwick A, Keon J, Gurr S, Hargreaves J. A single amino-acid substitution in the iron-sulphur protein subunit of succinate dehydrogenase determines resistance to carboxin in Mycosphaerella graminicola. Curr Genet. 1998;34:393-8 pubmed
    ..Mutants resistant to the fungicide carboxin (Cbx), a known inhibitor of Sdh, were found to contain a single amino-acid substitution in the third cysteine-..
  8. Ito Y, Muraguchi H, Seshime Y, Oita S, Yanagi S. Flutolanil and carboxin resistance in Coprinus cinereus conferred by a mutation in the cytochrome b560 subunit of succinate dehydrogenase complex (Complex II). Mol Genet Genomics. 2004;272:328-35 pubmed
    ..This sdhC mutation also conferred cross-resistance against another systemic fungicide, carboxin, an anilide that is structurally related to flutolanil...
  9. Ruprecht J, Yankovskaya V, Maklashina E, Iwata S, Cecchini G. Structure of Escherichia coli succinate:quinone oxidoreductase with an occupied and empty quinone-binding site. J Biol Chem. 2009;284:29836-46 pubmed publisher
    ..One with the specific quinone-binding site (Q-site) inhibitor carboxin present has been solved at 2.4 A resolution and reveals how carboxin inhibits the Q-site...

More Information

Publications52

  1. Yin Y, Kim Y, Xiao C. Molecular characterization of boscalid resistance in field isolates of Botrytis cinerea from apple. Phytopathology. 2011;101:986-95 pubmed publisher
    ..There was cross resistance between boscalid and carboxin. Analysis of partial sequences of the iron-sulfur subunit of succinate dehydrogenase gene in B...
  2. Keon J, White G, Hargreaves J. Isolation, characterization and sequence of a gene conferring resistance to the systemic fungicide carboxin from the maize smut pathogen, Ustilago maydis. Curr Genet. 1991;19:475-81 pubmed
    A gene which confers resistance to the systemic fungicide carboxin (Cbx) has been isolated from the maize pathogen, Ustilago maydis, by transferring a plasmid gene library from a Cbx-resistant mutant strain into a sensitive strain and ..
  3. Ando A, Sakuradani E, Horinaka K, Ogawa J, Shimizu S. Transformation of an oleaginous zygomycete Mortierella alpina 1S-4 with the carboxin resistance gene conferred by mutation of the iron-sulfur subunit of succinate dehydrogenase. Curr Genet. 2009;55:349-56 pubmed publisher
    ..residue within the third cysteine-rich cluster of SdhB replaced by a leucine residue) and is known to confer carboxin resistance. We succeeded in transforming M...
  4. Topp C, Ruiz Herrera J, Martinez Espinoza A, Gold S. Integration of the gene for carboxin resistance does not impact the Ustilago maydis-maize interaction. Curr Microbiol. 2002;44:67-70 pubmed
    A previous report indicated that insertion of the carboxin resistance (cbxR) gene into the Ustilago maydis genome impaired the pathogenic ability of the fungus towards Zea mays, the corn host...
  5. Henselová M, Hudecova D. Differences in the microflora of scarified and unscarified seeds of Karwinskia humboldtiana (Rhamnaceae). Folia Microbiol (Praha). 2001;46:543-8 pubmed
    ..Treatment of scarified seeds with Vitavax 200 WP and Pomarsol Forte 80 WP (3 mg/g seeds) augmented germination by 10-19% compared to treated unscarified seeds, and by 16-31% compared to untreated unscarified seeds...
  6. Myers M, Georgiou H, Byron S, Esposti M. Inhibition of mitochondrial oxidative phosphorylation induces hyper-expression of glutamic acid decarboxylase in pancreatic islet cells. Autoimmunity. 1999;30:43-51 pubmed
    ..These results represent the first evidence that GAD expression is enhanced under conditions that are toxic to pancreatic beta cells, and establish a link between mitochondrial dysfunction and expression of IDDM autoantigens...
  7. Keon J, Owen J, Hargreaves J. Lack of evidence for antisense suppression in the fungal plant pathogen Ustilago maydis. Antisense Nucleic Acid Drug Dev. 1999;9:101-4 pubmed
    ..This was despite detection of high levels of antisense RNA transcripts in cells transformed with the Pyr3 antisense vector...
  8. Adhikari N, Grover I. Genotoxic effects of some systemic pesticides: in vivo chromosomal aberrations in bone marrow cells in rats. Environ Mol Mutagen. 1988;12:235-42 pubmed
    ..It was observed that 2,4-D, dimecron, and vitavax were clastogenic, but the results obtained with benomyl and monocrotophos were equivocal...
  9. Irie T, Sato T, Saito K, Honda Y, Watanabe T, Kuwahara M, et al. Construction of a homologous selectable marker gene for Lentinula edodes transformation. Biosci Biotechnol Biochem. 2003;67:2006-9 pubmed
    ..protein (Ip) subunit from an edible mushroom, Lentinula edodes, and introduced a point mutation that confers carboxin resistance into it. The mutant gene successfully transformed L. edodes with high efficiency (9 transformants/2...
  10. Buckheit R, Snow M, Fliakas Boltz V, Kinjerski T, Russell J, Pallansch L, et al. Highly potent oxathiin carboxanilide derivatives with efficacy against nonnucleoside reverse transcriptase inhibitor-resistant human immunodeficiency virus isolates. Antimicrob Agents Chemother. 1997;41:831-7 pubmed
    ..The favorable anti-HIV properties of the UC compounds suggest they should be considered for further clinical development...
  11. Tsukihara T, Honda Y, Watanabe T, Watanabe T. Molecular breeding of white rot fungus Pleurotus ostreatus by homologous expression of its versatile peroxidase MnP2. Appl Microbiol Biotechnol. 2006;71:114-20 pubmed
    ..ostreatus strain by cotransformation with a carboxin-resistant marker plasmid...
  12. Shima Y, Ito Y, Hatabayashi H, Koma A, Yabe K. Five carboxin-resistant mutants exhibited various responses to carboxin and related fungicides. Biosci Biotechnol Biochem. 2011;75:181-4 pubmed
    Five carboxin-resistant mutants from Aspergillus oryzae were characterized by the sensitivities of their mycelial growth and succinate dehydrogenase (SDH) activity to carboxin and three related fungicides...
  13. Brinck T, Jin P, Ma Y, Murray J, Politzer P. Segmental analysis of molecular surface electrostatic potentials: application to enzyme inhibition. J Mol Model. 2003;9:77-83 pubmed
    ..This initial exploratory study shows that segmental analysis can provide insight into the nature of the process being investigated, as well as possibly enhancing the predictive capability...
  14. Iesce M, Cermola F, De Lorenzo F, Graziano M, Caliendo B. Photochemical behaviour of the systemic fungicide carboxin. Environ Sci Pollut Res Int. 2002;9:107-9 pubmed
    Irradiation of carboxin (1) with a 500 W UV lamp (filter Pyrex) in CH3CN leads to the products 3, 5-8, 12-14 depending upon the reaction conditions. All photo-products were isolated and characterized...
  15. Deng Y, Nicholson R. Stimulation by surangin B of endogenous amino acid release from synaptosomes. Toxicon. 2003;42:351-7 pubmed
    ..CCCP; an uncoupler), were more potent releasers of amino acids from synaptosomes than surangin B, however, carboxin (a complex II-selective inhibitor), was extremely weak to ineffective in this regard...
  16. Bader J, McMahon J, Schultz R, Narayanan V, Pierce J, Harrison W, et al. Oxathiin carboxanilide, a potent inhibitor of human immunodeficiency virus reproduction. Proc Natl Acad Sci U S A. 1991;88:6740-4 pubmed
    ..OC represents a new class of anti-HIV agents that are promising candidates for drug development...
  17. Ren J, Esnouf R, Hopkins A, Warren J, Balzarini J, Stuart D, et al. Crystal structures of HIV-1 reverse transcriptase in complex with carboxanilide derivatives. Biochemistry. 1998;37:14394-403 pubmed
    ..This in turn explains the differences in the effect of mutated residues on the binding of these compounds...
  18. Balzarini J, Pérez Pérez M, Velazquez S, San Felix A, Camarasa M, De Clercq E, et al. Suppression of the breakthrough of human immunodeficiency virus type 1 (HIV-1) in cell culture by thiocarboxanilide derivatives when used individually or in combination with other HIV-1-specific inhibitors (i.e., TSAO derivatives). Proc Natl Acad Sci U S A. 1995;92:5470-4 pubmed
  19. Joseph Horne T, Wood P, Wood C, Moore A, Headrick J, Hollomon D. Characterization of a split respiratory pathway in the wheat "take-all" fungus, Gaeumannomyces graminis var. tritici. J Biol Chem. 1998;273:11127-33 pubmed
    ..graminis tritici. These results are discussed in relation to current understanding of fungal electron transfer and to the possible contribution of alternative redox centers in ATP synthesis...
  20. Kinjerski T, Buckheit R. The role of genotypic heterogeneity in wild type virus populations on the selection of nonnucleoside reverse transcriptase inhibitor-resistant viruses. Antiviral Res. 1997;33:109-15 pubmed
  21. Hahn H, Rhee H, Lee C, Whang K. Designs and syntheses of oxathiin carboxanilide analogues and their antiviral activities. Arch Pharm Res. 2000;23:315-23 pubmed
    ..But the trifluoromethylated dithiin (24f) showed higher inhibitory activity against PV-1 and CoxB-3 virus than commercial antiviral agents, ribavirin (RV)...
  22. Ngari C, Combier J, Dore J, Marmeisse R, Gay G, Melayah D. The dominant Hc.Sdh (R) carboxin-resistance gene of the ectomycorrhizal fungus Hebeloma cylindrosporum as a selectable marker for transformation. Curr Genet. 2009;55:223-31 pubmed publisher
    ..Sdh (R) that confers carboxin-resistance was isolated from a UV mutant of this fungus...
  23. Ahmad M, Javed F, Ashraf M, Hafeez F. Effect of fungicide seed treatments on N2-fixation and nodulation in pea, Pisum sativum L. Bull Environ Contam Toxicol. 2006;77:896-904 pubmed
  24. Fletcher R, Arion D, Borkow G, Wainberg M, Dmitrienko G, Parniak M. Synergistic inhibition of HIV-1 reverse transcriptase DNA polymerase activity and virus replication in vitro by combinations of carboxanilide nonnucleoside compounds. Biochemistry. 1995;34:10106-12 pubmed
    ..We believe this to be the first example of synergistic inhibition of HIV-1 RT by combinations of structurally related nonnucleoside inhibitors...
  25. Fletcher R, Syed K, Mithani S, Dmitrienko G, Parniak M. Carboxanilide derivative non-nucleoside inhibitors of HIV-1 reverse transcriptase interact with different mechanistic forms of the enzyme. Biochemistry. 1995;34:4346-53 pubmed
    ..In contrast, UC38 completely photoprotected the RT-P/T-dNTP ternary complex, but not free RT or the RT-P/T binary complex. UC84 and UC38 thus appear to bind to different mechanistic forms of RT in the polymerase reaction sequence...
  26. Kojic M, Holloman W. Shuttle vectors for genetic manipulations in Ustilago maydis. Can J Microbiol. 2000;46:333-8 pubmed
    ..Sets of plasmids selectable in media containing geneticin, carboxin, nourseothricin, or hygromycin, able to replicate autonomously, to transform U...
  27. Borkow G, Barnard J, Nguyen T, Belmonte A, Wainberg M, Parniak M. Chemical barriers to human immunodeficiency virus type 1 (HIV-1) infection: retrovirucidal activity of UC781, a thiocarboxanilide nonnucleoside inhibitor of HIV-1 reverse transcriptase. J Virol. 1997;71:3023-30 pubmed
    ..These unique properties of UC781 indicate that this nonnucleoside inhibitor may have considerable promise for use in retrovirucidal formulations to minimize the spread of HIV from infected to noninfected individuals...
  28. Obermayer D, Glasnov T, Kappe C. Microwave-assisted and continuous flow multistep synthesis of 4-(pyrazol-1-yl)carboxanilides. J Org Chem. 2011;76:6657-69 pubmed publisher
  29. Esnouf R, Stuart D, De Clercq E, Schwartz E, Balzarini J. Models which explain the inhibition of reverse transcriptase by HIV-1-specific (thio)carboxanilide derivatives. Biochem Biophys Res Commun. 1997;234:458-64 pubmed
    ..They further predict that mutations to Phe227, Trp229, or Leu234 might confer resistance. Since these are not observed, some constraining structural or functional role for these residues in the active enzyme is suggested...
  30. Miki T. [Inhibitors of complex I and II of the mitochondrial respiratory chain]. Nihon Rinsho. 2002;60 Suppl 4:171-4 pubmed
  31. Hederstedt L. Succinate:quinone oxidoreductase in the bacteria Paracoccus denitrificans and Bacillus subtilis. Biochim Biophys Acta. 2002;1553:74-83 pubmed
    ..oxidoreductase that is similar to that of mammalian mitochondria with respect to composition and sensitivity to carboxin. Results obtained with carboxin-resistant P...
  32. McMahon J, Buckheit R, Gulakowski R, Currens M, Vistica D, Shoemaker R, et al. Biological and biochemical anti-human immunodeficiency virus activity of UC 38, a new non-nucleoside reverse transcriptase inhibitor. J Pharmacol Exp Ther. 1996;276:298-305 pubmed
    ..The favorable physical characteristics, lack of toxicity, potency and bioavailability of UC 38 may make it a candidate for combination chemotherapy of acquired immune deficiency syndrome...
  33. Kano S, Akagi K, Kanematsu S, Morinaga T. Cloning and characterization of the gene for the iron-sulfur subunit of succinate dehydrogenase from the violet root rot fungus, Helicobasidium mompa. J Basic Microbiol. 2012;52:132-40 pubmed publisher
    ..One of these clusters contains a critical histidine residue implicated in carboxin sensitivity in the basidiomycetes. Only one copy of the gene was present in the genome of H...
  34. Balzarini J, Brouwer W, Felauer E, De Clercq E, Karlsson A. Activity of various thiocarboxanilide derivatives against wild-type and several mutant human immunodeficiency virus type 1 strains. Antiviral Res. 1995;27:219-36 pubmed
    ..One of the most potent HIV-1 inhibitors among the thiocarboxanilide derivatives, namely UC38, selected for a mutant virus strain in which Lys at position 101 and Gly at position 190 of the reverse transcriptase was replaced by Glu...
  35. Kim J, Mahoney N, Chan K, Molyneux R, Campbell B. Controlling food-contaminating fungi by targeting their antioxidative stress-response system with natural phenolic compounds. Appl Microbiol Biotechnol. 2006;70:735-9 pubmed
    ..g., vanillyl acetone) resulted in a 100- to 1,000-fold greater sensitivity to strobilurin or carboxin fungicides...
  36. van Herk W, Vernon R. Soil bioassay for studying behavioral responses of wireworms (Coleoptera: Elateridae) to insecticide-treated wheat seed. Environ Entomol. 2007;36:1441-9 pubmed
    ..Wireworms exposed to Vitavax Dual (containing the organochlorine lindane) were not repelled after feeding and showed symptoms of illness for up to 28 d before making a full recovery (89%) or dying (11%)...
  37. Balzarini J, Brouwer W, Dao D, Osika E, De Clercq E. Identification of novel thiocarboxanilide derivatives that suppress a variety of drug-resistant mutant human immunodeficiency virus type 1 strains at a potency similar to that for wild-type virus. Antimicrob Agents Chemother. 1996;40:1454-66 pubmed
    ..UC-781 and UC-82 should be considered potential candidate drugs for the treatment of HIV-1-infected individuals...
  38. Buckheit R, Kinjerski T, Fliakas Boltz V, Russell J, Stup T, Pallansch L, et al. Structure-activity and cross-resistance evaluations of a series of human immunodeficiency virus type-1-specific compounds related to oxathiin carboxanilide. Antimicrob Agents Chemother. 1995;39:2718-27 pubmed
    ..The merits of selecting potential candidate anti-HIV agents to be used in rational combination drugs design as part of an armamentarium of highly active anti-HIV compounds are discussed...
  39. Ortiz Alvarado R, Gonzalez Hernandez G, Torres Guzman J, Gutierrez Corona J. Transformation of Mucor circinelloides with autoreplicative vectors containing homologous and heterologous ARS elements and the dominant Cbx(r) carboxine-resistance gene. Curr Microbiol. 2006;52:178-81 pubmed
    ..The presence of autoreplicating plasmid molecules in the transformants was demonstrated by mitotic stability experiments, by Southern analysis, and by the rescue of plasmids from transformed bacterial cells...
  40. Matsson M, Hederstedt L. The carboxin-binding site on Paracoccus denitrificans succinate:quinone reductase identified by mutations. J Bioenerg Biomembr. 2001;33:99-105 pubmed
    Succinate:quinone reductase catalyzes electron transfer from succinate to quinone in aerobic respiration. Carboxin is a specific inhibitor of this enzyme from several different organisms...
  41. Dellagreca M, Iesce M, Cermola F, Rubino M, Isidori M. Phototransformation of carboxin in water. Toxicity of the pesticide and its sulfoxide to aquatic organisms. J Agric Food Chem. 2004;52:6228-32 pubmed
    Sunlight exposure of aqueous suspensions of carboxin (1) causes its phototransformation to sulfoxide 2 and minor components. Similar effects are observed in the presence of humic acid or nitrate or at different pH values...
  42. Nomeir A, McComish M, Ferrala N, Silveira D, Covey J, Chadwick M. Liquid chromatographic analysis in mouse, dog and human plasma; stability, absorption, metabolism and pharmacokinetics of the anti-HIV agent 2-chloro-5-(2-methyl-5,6-dihydro-1,4-oxathiin-3-yl carboxamido) isopropylbenzoate (NSC 615985, UC84). J Pharm Biomed Anal. 1998;17:27-38 pubmed
  43. Scalliet G, Bowler J, Luksch T, Kirchhofer Allan L, Steinhauer D, Ward K, et al. Mutagenesis and functional studies with succinate dehydrogenase inhibitors in the wheat pathogen Mycosphaerella graminicola. PLoS ONE. 2012;7:e35429 pubmed publisher