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Chemical Compound Review

Furamidine     4-[5-(4-carbamimidoylphenyl)- 2...

Synonyms: Furandiamidine, CHEMBL24057, DB75, SureCN549198, AG-F-93517, ...
 
 
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Disease relevance of Furandiamidine

 

High impact information on Furandiamidine

  • Distribution of furamidine analogues in tumor cells: targeting of the nucleus or mitochondria depending on the amidine substitution [3].
  • Compounds 10a, 10b, 10d, 18a, and 18b show IC50 values of 5 nM or less against Trypanosoma brucei rhodesiense (T. b. r.) and 10a, 10b, 10e, 18a, and 18b gave similar ones against Plasmodium falciparum (P.f.). The dications, 10a, 10d, 10f, and 10g are more active than furamidine in vivo [4].
  • Accurate quantification of binding affinities by surface plasmon resonance using A(n)T(n) hairpin oligomer indicated that the interaction of DB950 is over 10-50 times stronger than that of ethidium and comparable to that of the known minor groove binder furamidine [5].
  • The high-resolution fluorescence pictures show that in the furamidine series, the compounds with two or four positive charges selectively accumulate in the cell nuclei whereas, in most cases, those bearing only one positive charge show reduced cell uptake capacities [6].
  • 2,5-Bis(4-guanylphenyl)furan ("furamidine") is a dicationic minor groove binding drug that has been shown to be more effective than pentamidine against the Pneumocystis carinii pathogen in an immunosuppressed rat model [7].
 

Biological context of Furandiamidine

  • An X-ray structure for the complex of the dicationic amidine derivative, 2,5-bis(4-guanylphenyl)furan (1), with the oligomer demonstrates the snug fit of these compounds with the AATT minor-groove binding site and hydrogen bonds to AT base pairs at the floor of the minor groove [8].
  • These results indicate that cytochrome b5 and b5 reductase play a direct role in metabolic activation of DB289 to furamidine [9].
  • As part of an effort to develop additional and improved diamidines against African trypanosomes, CoMFA and CoMSIA 3D QSAR analyses have been conducted with furamidine and a set of 25 other structurally related compounds [2].
 

Associations of Furandiamidine with other chemical compounds

References

  1. Characterization of a novel DNA minor-groove complex. Nguyen, B., Hamelberg, D., Bailly, C., Colson, P., Stanek, J., Brun, R., Neidle, S., Wilson, W.D. Biophys. J. (2004) [Pubmed]
  2. 3D QSAR on a library of heterocyclic diamidine derivatives with antiparasitic activity. Athri, P., Wenzler, T., Ruiz, P., Brun, R., Boykin, D.W., Tidwell, R., Wilson, W.D. Bioorg. Med. Chem. (2006) [Pubmed]
  3. Distribution of furamidine analogues in tumor cells: targeting of the nucleus or mitochondria depending on the amidine substitution. Lansiaux, A., Tanious, F., Mishal, Z., Dassonneville, L., Kumar, A., Stephens, C.E., Hu, Q., Wilson, W.D., Boykin, D.W., Bailly, C. Cancer Res. (2002) [Pubmed]
  4. Synthesis, DNA affinity, and antiprotozoal activity of linear dications: Terphenyl diamidines and analogues. Ismail, M.A., Arafa, R.K., Brun, R., Wenzler, T., Miao, Y., Wilson, W.D., Generaux, C., Bridges, A., Hall, J.E., Boykin, D.W. J. Med. Chem. (2006) [Pubmed]
  5. Molecular determinants for DNA minor groove recognition: design of a bis-guanidinium derivative of ethidium that is highly selective for AT-rich DNA sequences. Bailly, C., Arafa, R.K., Tanious, F.A., Laine, W., Tardy, C., Lansiaux, A., Colson, P., Boykin, D.W., Wilson, W.D. Biochemistry (2005) [Pubmed]
  6. Distribution of furamidine analogues in tumor cells: influence of the number of positive charges. Lansiaux, A., Dassonneville, L., Facompré, M., Kumar, A., Stephens, C.E., Bajic, M., Tanious, F., Wilson, W.D., Boykin, D.W., Bailly, C. J. Med. Chem. (2002) [Pubmed]
  7. A crystallographic and spectroscopic study of the complex between d(CGCGAATTCGCG)2 and 2,5-bis(4-guanylphenyl)furan, an analogue of berenil. Structural origins of enhanced DNA-binding affinity. Laughton, C.A., Tanious, F., Nunn, C.M., Boykin, D.W., Wilson, W.D., Neidle, S. Biochemistry (1996) [Pubmed]
  8. Dicationic diarylfurans as anti-Pneumocystis carinii agents. Boykin, D.W., Kumar, A., Spychala, J., Zhou, M., Lombardy, R.J., Wilson, W.D., Dykstra, C.C., Jones, S.K., Hall, J.E., Tidwell, R.R. J. Med. Chem. (1995) [Pubmed]
  9. Unusual dehydroxylation of antimicrobial amidoxime prodrugs by cytochrome b5 and NADH cytochrome b5 reductase. Saulter, J.Y., Kurian, J.R., Trepanier, L.A., Tidwell, R.R., Bridges, A.S., Boykin, D.W., Stephens, C.E., Anbazhagan, M., Hall, J.E. Drug Metab. Dispos. (2005) [Pubmed]
  10. Trypanocidal activity of the phenyl-substituted analogue of furamidine DB569 against Trypanosoma cruzi infection in vivo. de Souza, E.M., Oliveira, G.M., Boykin, D.W., Kumar, A., Hu, Q., De Nazaré C Soeiro, M. J. Antimicrob. Chemother. (2006) [Pubmed]
  11. Trypanosoma rhodesiense: evaluation of the antitrypanosomal action of 2,5-bis(4-guanylphenyl)furan dihydrochloride. Steck, E.A., Kinnamon, K.E., Davidson, D.E., Duxbury, R.E., Johnson, A.J., Masters, R.E. Exp. Parasitol. (1982) [Pubmed]
  12. Inhibition of HIV-1 Tat-TAR interaction by diphenylfuran derivatives: effects of the terminal basic side chains. Gelus, N., Bailly, C., Hamy, F., Klimkait, T., Wilson, W.D., Boykin, D.W. Bioorg. Med. Chem. (1999) [Pubmed]
 
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