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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 
Chemical Compound Review

Proflavin     acridine-3,6-diamine

Synonyms: Profura, Progarmed, Proflavina, Proflavine, Proflavinum, ...
 
 
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Disease relevance of Proflavine

 

High impact information on Proflavine

  • The structure of the complex formed between the intercalating agent proflavine and fibrous native DNA was studied by one- and two-dimensional high-resolution solid-state nuclear magnetic resonance (NMR) [6].
  • The UVCD equilibrium-binding studies revealed identical affinities of Pf for QacR in the presence or absence of Et, but significantly diminished affinity of Et for QacR when Pf is prebound, findings that are readily explicable by their structures [3].
  • Frameshift mutations were induced by proflavin in the rIIB gene of bacteriophage T4. rIIB DNA from each of 48 independent frameshifts was inserted into M13mp8 and sequenced [4].
  • The patterns of the base sequence changes suggest that two specific phosphodiester bonds within the hotspot sequence are sites at which proflavin-induced mutation is initiated [4].
  • Transient removal of proflavine inhibition of bovine beta-trypsin by the bovine basic pancreatic trypsin inhibitor (Kunitz). A case for "chronosteric effects" [7].
 

Chemical compound and disease context of Proflavine

 

Biological context of Proflavine

  • When alpha-chymotrypsin in unbuffered solution at pH 7 is mixed with buffered proflavin by stopped flow instrumentation to give a final pH of 3.89, a decrease in active sites occurs, as measured by a decrease in enzyme-dye complex [13].
  • One proflavin is asymmetrically intercalated between the base pairs and the other is stacked above them [14].
  • The kinetics of the reaction were followed by monitoring either the intensity or the polarization of the fluorescence of both wybutine and proflavine located in the anticodon loop or of proflavine located in the D loop of yeast tRNAPhe or N-AcPhe-tRNAPhe [15].
  • The role of DNA sequence-specific interactions of proflavin with DNA in proflavin mutagenesis is discussed [16].
  • This increase is (i) caused by an increase in the solid support-free mu (muo) of the procapsid, not a decrease in its radius, and (ii) not prevented by either genetically or chemically (use of proflavine) blocking DNA packaging [17].
 

Anatomical context of Proflavine

  • The direct effect of proflavine on these processes, as monitored in a reconstituted cell-free system, supports the theory that base-paired segments (i.e. hairpin loops) in the precursor RNA's are involved as recognition sites in nuclear RNA processing [18].
  • Flow cytometric analysis of proflavine uptake into normal rat hepatocytes and cells arising during AAF-induced hepatocarcinogenesis [19].
  • We examined the possibility that the transfer involved membrane-bound vesicles, by taking advantage of the fact that the fluorescent compound, 3,6-acridinediamine, N,N,N,',N'-tetramethylmonohydride [acridine orange (AO)], rapidly and selectively stains vesicular structures in glial cells surrounding the giant axon [20].
  • Peripheral blood lymphocytes from normal donors were exposed to mitomycin C 0.01 microgram/ml, proflavine 0.4 microgram/ml, and 3H-uridine 3.7 Bq/ml and analyzed for the incidence of sister chromatid exchanges (SCEs) [21].
  • Equilibria and kinetics of the intercalation of Pt-proflavine and proflavine into calf thymus DNA [22].
 

Associations of Proflavine with other chemical compounds

  • Additional experiments showed that binding to thrombin of two competitive thrombin inhibitors, i.e. proflavin and p-aminobenzamidine, is characterized by a change in the standard heat capacity change (delta Cp), approximately equal to -1 kcal/mol K [23].
  • In vitro studies showed that methylene blue, neutral red, and proflavine were capable of killing these fungi when used in conjunction with broad-spectrum light [24].
  • No significant differences were found for the antithrombin reactions (measured by proflavin displacement or active site titration) with respect to kinetics, extent of reaction, or effect of added heparin [25].
  • Several other 9-anilinoacridine derivatives, and also 9-hydroxyellipticine, caused quenching of ethidium-DNA fluorescence, whereas 9-aminoacridine, proflavin, and ellipticine had no effect [26].
  • Values for the acylation rate constant, k2, and the binding constant, KS, were obtained by using measurements of phenolate release, for the p-nitrophenyl esters, and proflavin displacement, for the ethyl esters [27].
 

Gene context of Proflavine

  • The observation that proflavine competes with Rev for binding to RRE-IIB by binding as a dimer to a single high-affinity site opens the possibility for rational drug design based on linking and modifying it and related compounds [28].
  • In cultures at a specific stage, proflavine showed decreased mutagenesis in a recA as compared with a wildtupe or uvrB derivative [29].
  • Proflavine was bound most strongly to PLA2 and Ans and Tns were bound to the three proteins with comparable affinities [30].
  • The effect of proflavine on pyruvate kinase I of Escherichia coli B [31].
  • The formation of the bovine beta-trypsin-bovine basic pancreatic trypsin inhibitor (Kunitz) (BPTI) complex was monitored, making use of three different signals: proflavine displacement, optical density changes in the ultraviolet region, and the loss of the catalytic activity [7].
 

Analytical, diagnostic and therapeutic context of Proflavine

References

  1. Measles virus: an unwanted variant causing hydrocephalus. Haspel, M.V., Rapp, F. Science (1975) [Pubmed]
  2. Tumor virus induction and host cell capacity inactivation: possible in vitro tests for photosensitizing chemicals. Bockstahler, L.E., Coohill, T.P., Lytle, C.D., Moore, S.P., Cantwell, J.M., Schmidt, B.J. J. Natl. Cancer Inst. (1982) [Pubmed]
  3. Structural mechanism of the simultaneous binding of two drugs to a multidrug-binding protein. Schumacher, M.A., Miller, M.C., Brennan, R.G. EMBO J. (2004) [Pubmed]
  4. Frameshift mutations produced by proflavin in bacteriophage T4: specificity within a hotspot. Ripley, L.S., Clark, A. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  5. On the fidelity of DNA replication. Specificity of nucleotide substitution by intercalating agents. Shearman, C.W., Loeb, L.A. J. Biol. Chem. (1983) [Pubmed]
  6. Intercalation complex of proflavine with DNA: structure and dynamics by solid-state NMR. Tang, P., Juang, C.L., Harbison, G.S. Science (1990) [Pubmed]
  7. Transient removal of proflavine inhibition of bovine beta-trypsin by the bovine basic pancreatic trypsin inhibitor (Kunitz). A case for "chronosteric effects". Antonini, E., Ascenzi, P., Bolognesi, M., Menegatti, E., Guarneri, M. J. Biol. Chem. (1983) [Pubmed]
  8. Fluorescence studies of the accessibility of the 3' ends of the ribosomal RNAs in Escherichia coli ribosomes and subunits. Schreiber, J.P., Hsiung, N., Cantor, C.R. Nucleic Acids Res. (1979) [Pubmed]
  9. Photodynamic treatment of herpes simplex virus during its replicative cycle. Khan, N.C., Melnick, J.L., Biswal, N. J. Virol. (1977) [Pubmed]
  10. Isolation and preliminary characterization of temperature-sensitive mutants of measles virus. Haspel, M.V., Duff, R., Rapp, F. J. Virol. (1975) [Pubmed]
  11. Mutagenesis by ethidium bromide, proflavine and mitomycin C in the cyanobacterium Nostoc sp. Tripathi, A.K., Kumar, H.D. Mutat. Res. (1986) [Pubmed]
  12. Alteration of guanine residues during proflavine mediated photosensitization of DNA. Piette, J., Calberg-Bacq, C.M., Van de Vorst, A. Photochem. Photobiol. (1981) [Pubmed]
  13. Kinetics of alpha-chymotrypsin dimerization. Gilleland, M.J., Bender, M.L. J. Biol. Chem. (1976) [Pubmed]
  14. The structure of drug-deoxydinucleoside phosphate complex; generalized conformational behavior of intercalation complexes with RNA and DNA fragments. Shieh, H.S., Berman, H.M., Dabrow, M., Neidle, S. Nucleic Acids Res. (1980) [Pubmed]
  15. Pre-steady-state kinetics of ribosomal translocation. Robertson, J.M., Paulsen, H., Wintermeyer, W. J. Mol. Biol. (1986) [Pubmed]
  16. Effects of proflavin and photoactivated proflavin on the template function of single-stranded DNA. Revich, G.G., Ripley, L.S. J. Mol. Biol. (1990) [Pubmed]
  17. Heterogeneity of the procapsid of bacteriophage T3. Serwer, P., Watson, R.H., Hayes, S.J. J. Virol. (1985) [Pubmed]
  18. Proflavine sensitivity of RNA processing in isolated nuclei. Yannarell, A., Niemann, M., Schumm, D.E., Webb, T.E. Nucleic Acids Res. (1977) [Pubmed]
  19. Flow cytometric analysis of proflavine uptake into normal rat hepatocytes and cells arising during AAF-induced hepatocarcinogenesis. Austin, E.B., Holmes, C.H., Robins, R.A., Baldwin, R.W. Carcinogenesis (1984) [Pubmed]
  20. Transfer of molecules from glia to axon in the squid may be mediated by glial vesicles. Buchheit, T.E., Tytell, M. J. Neurobiol. (1992) [Pubmed]
  21. Variation in the sensitivity of human lymphocytes to DNA-damaging agents measured by sister chromatid exchange frequency. Crossen, P.E. Hum. Genet. (1982) [Pubmed]
  22. Equilibria and kinetics of the intercalation of Pt-proflavine and proflavine into calf thymus DNA. Biver, T., Secco, F., Tinè, M.R., Venturini, M. Arch. Biochem. Biophys. (2003) [Pubmed]
  23. Thermodynamics of substrates and reversible inhibitors binding to the active site cleft of human alpha-thrombin. De Cristofaro, R., Landolfi, R. J. Mol. Biol. (1994) [Pubmed]
  24. In vitro and in vivo photosensitized inactivation of dermatophyte fungi by heterotricyclic dyes. Propst, C., Lubin, L. Infect. Immun. (1978) [Pubmed]
  25. Antithrombin reactions with alpha- and gamma-thrombins. Chang, T., Feinman, R.D., Landis, B.H., Fenton, J.W. Biochemistry (1979) [Pubmed]
  26. Quenching of DNA-ethidium fluorescence by amsacrine and other antitumor agents: a possible electron-transfer effect. Baguley, B.C., Le Bret, M. Biochemistry (1984) [Pubmed]
  27. Binding rates, O--S substitution effects, and the pH dependence of chymotrypsin reactions. Hirohara, H., Philipp, M., Bender, M.L. Biochemistry (1977) [Pubmed]
  28. Proflavine acts as a Rev inhibitor by targeting the high-affinity Rev binding site of the Rev responsive element of HIV-1. DeJong, E.S., Chang, C.E., Gilson, M.K., Marino, J.P. Biochemistry (2003) [Pubmed]
  29. Variation in the mutagenic potential of acridines in Salmonella typhimurium, with stage of the culture. Ferguson, L.R., Pogai, H., Turner, P.M. Mutat. Res. (1991) [Pubmed]
  30. Interactions of Trimeresurus flavoviridis phospholipase A2 and its N-terminal octapeptide-removed and p-bromophenacylated derivatives with acridine and anilinonaphthalene dyes. Oda, N., Yoshida, M., Tanaka, S., Kihara, H., Ohno, M. J. Biochem. (1986) [Pubmed]
  31. The effect of proflavine on pyruvate kinase I of Escherichia coli B. McKellar, R.C., Kushner, D.J. Can. J. Biochem. (1977) [Pubmed]
  32. Formate dehydrogenase from Methylosinus trichosporium OB3b. Purification and spectroscopic characterization of the cofactors. Jollie, D.R., Lipscomb, J.D. J. Biol. Chem. (1991) [Pubmed]
  33. Treatment of genital herpes simplex virus infection with photodynamic inactivation. Kaufman, R.H., Adam, E., Mirkovic, R.R., Melnick, J.L., Young, R.L. Am. J. Obstet. Gynecol. (1978) [Pubmed]
  34. Fractionation of of proteolytic enzymes by affinity chromatography on sepharose aminocaproyl proflavin. Brantner, J.H., Medicus, R.G., McRorie, R.A. J. Chromatogr. (1976) [Pubmed]
 
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