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Chemical Compound Review

Imidole     1H-pyrrole

Synonyms: PYROLLE, PYRROLE, Pyrrol, Azole, Monopyrrole, ...
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Disease relevance of Imidole

  • It is reported for the first time that direct electron-transfer processes between a polypyrrole (PPY) entrapped quinohemoprotein alcohol dehydrogenase from Gluconobacter sp. 33 (QH-ADH) and a platinum electrode take place via the conducting-polymer network [1].
  • The genotypes of 75 DNA genomic samples from colorectal cancer patients were analyzed side by side using direct DNA sequencing and a polypyrrole DNA chip [2].
  • The binding properties of a set of four hybrids, prepared combining from one to four polypyrrole minor groove binders and pyrrolo [2,1-c][1,4]benzodiazepine (PBD), have been studied using as target molecule the HIV-1 TAR-RNA [3].
  • Molecularly imprinted polypyrrole-based synthetic receptor for direct detection of bovine leukemia virus glycoproteins [4].
  • Electrode arrays were used to electroaddress various bioconjugate structures comprising a recombinant HIV-1 P24 capsid protein (RH24K) in polypyrrole film [5].

High impact information on Imidole

  • Interdomain flexibility may aid elongation of the polypyrrole product in the active-site cleft of the enzyme [6].
  • Human indoleamine 2,3-dioxygenase (IDO) catalyzes the cleavage of the pyrrol ring of L-Trp and incorporates both atoms of a molecule of oxygen (O2) [7].
  • The median neurite length for PC-12 cells grown on PP and subjected to an electrical stimulus was 18.14 micron (n = 5643) compared with 9.5 micron (n = 4440) for controls [8].
  • However, PC-12 cells cultured on PP films and subjected to an electrical stimulus through the film showed a significant increase in neurite lengths compared with ones that were not subjected to electrical stimulation through the film and tissue culture polystyrene controls [8].
  • In this paper, the electrically conductive polymer--oxidized polypyrrole (PP)--has been evaluated for use as a substrate to enhance nerve cell interactions in culture as a first step toward potentially using such polymers to stimulate in vivo nerve regeneration [8].

Chemical compound and disease context of Imidole

  • Torsion angles between adjacent rings in polypyrrole and polythiophene conducting polymers are related to conjugation length and the conductivity properties of the polymer materials [9].

Biological context of Imidole


Anatomical context of Imidole

  • When aortic endothelial cells were cultured on fibronectin-coated polypyrrole (oxidized) in either chemically defined medium or the presence of serum, cells spread normally and synthesized DNA [14].
  • In vitro studies demonstrated that extracellular matrix molecules, such as fibronectin, adsorb efficiently onto polypyrrole thin films and support cell attachment under serum-free conditions [14].
  • Compared with commercial capillaries that were currently used for in-tube SPME, the PPY-coated capillary showed better extraction efficiency for all of the compounds studied [15].
  • With respect to antiproliferative effects, it was found that the increase in the length of the polypyrrole backbone leads to an increase of in vitro antiproliferative effects, i.e., the hybrid 25 containing the four pyrroles is more active than 22, 23, and 24 both against K562 and Jurkat cell lines [12].
  • Polypyrrole (PPy) nanotubes with highly uniform surface and tunable wall thickness were fabricated by one-step vapor deposition polymerization (VDP) using anodic aluminium oxide (AAO) template membranes, and transformed into carbon nanotubes through a carbonization process [16].

Associations of Imidole with other chemical compounds


Gene context of Imidole

  • Keratinocytes stained positive for PCNA (proliferation), K10 (suprabasal differentiation), and K16 (hyperproliferation) markers although cell morphology was poor for organotypical cultures on dermatan- loaded polypyrrole compared with de-epidermalized dermis [21].
  • Carrier dynamics in conducting polymers: case of PF6 doped polypyrrole [22].
  • The composite CPEs were prepared by in situ generation of polypyrrole (PPy) within a paste containing the enzyme polyphenol oxidase (PPO) [23].
  • We describe a method based on polypyrrole DNA chip technology to detect K-ras gene mutations in tumors [2].
  • Thus, by coating it with a cross-linked film of catalase and albumin, the upper sensing limit of a peroxidase-incorporated polypyrrole membrane electrode as an H2O2 sensor was raised by approximately 2 orders of magnitude [24].

Analytical, diagnostic and therapeutic context of Imidole


  1. Polypyrrole-entrapped quinohemoprotein alcohol dehydrogenase. Evidence for direct electron transfer via conducting-polymer chains. Ramanavicius, A., Habermuller, K., Csöregi, E., Laurinavicius, V., Schuhmann, W. Anal. Chem. (1999) [Pubmed]
  2. K-ras mutation detection by hybridization to a polypyrrole DNA chip. Lopez-Crapez, E., Livache, T., Marchand, J., Grenier, J. Clin. Chem. (2001) [Pubmed]
  3. Binding of hybrid molecules containing pyrrolo [2,1-c][1,4]benzodiazepine (PBD) and oligopyrrole carriers to the human immunodeficiency type 1 virus TAR-RNA. Mischiati, C., Finotti, A., Sereni, A., Boschetti, S., Baraldi, P.G., Romagnoli, R., Feriotto, G., Jeang, K.T., Bianchi, N., Borgatti, M., Gambari, R. Biochem. Pharmacol. (2004) [Pubmed]
  4. Molecularly imprinted polypyrrole-based synthetic receptor for direct detection of bovine leukemia virus glycoproteins. Ramanaviciene, A., Ramanavicius, A. Biosensors & bioelectronics. (2004) [Pubmed]
  5. Electroaddressed immobilization of recombinant HIV-1 P24 capsid protein onto screen-printed arrays for serological testing. Marquette, C.A., Imbert-Laurenceau, E., Mallet, F., Chaix, C., Mandrand, B., Blum, L.J. Anal. Biochem. (2005) [Pubmed]
  6. Structure of porphobilinogen deaminase reveals a flexible multidomain polymerase with a single catalytic site. Louie, G.V., Brownlie, P.D., Lambert, R., Cooper, J.B., Blundell, T.L., Wood, S.P., Warren, M.J., Woodcock, S.C., Jordan, P.M. Nature (1992) [Pubmed]
  7. Crystal structure of human indoleamine 2,3-dioxygenase: catalytic mechanism of O2 incorporation by a heme-containing dioxygenase. Sugimoto, H., Oda, S., Otsuki, T., Hino, T., Yoshida, T., Shiro, Y. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  8. Stimulation of neurite outgrowth using an electrically conducting polymer. Schmidt, C.E., Shastri, V.R., Vacanti, J.P., Langer, R. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  9. N-Benzyl-2,5-bis(2-thienyl)pyrrole. Palenzuela Conde, J., Elsegood, M.R., Ryder, K.S. Acta crystallographica. Section C, Crystal structure communications. (2004) [Pubmed]
  10. Label-free DNA detection based on modified conducting polypyrrole films at microelectrodes. Riccardi, C.d.o.s. .S., Yamanaka, H., Josowicz, M., Kowalik, J., Mizaikoff, B., Kranz, C. Anal. Chem. (2006) [Pubmed]
  11. Sequence specificity of alkylation for a series of nitrogen mustard-containing analogues of distamycin of increasing binding site size: evidence for increased cytotoxicity with enhanced sequence specificity. Wyatt, M.D., Lee, M., Garbiras, B.J., Souhami, R.L., Hartley, J.A. Biochemistry (1995) [Pubmed]
  12. Synthesis, in vitro antiproliferative activity, and DNA-binding properties of hybrid molecules containing pyrrolo[2,1-c][1, 4]benzodiazepine and minor-groove-binding oligopyrrole carriers. Baraldi, P.G., Balboni, G., Cacciari, B., Guiotto, A., Manfredini, S., Romagnoli, R., Spalluto, G., Thurston, D.E., Howard, P.W., Bianchi, N., Rutigliano, C., Mischiati, C., Gambari, R. J. Med. Chem. (1999) [Pubmed]
  13. Detection of single nucleotide polymorphisms by minisequencing on a polypyrrole DNA chip designed for medical diagnosis. Ho-Pun-Cheung, A., Choblet, S., Colineau, T., Abaibou, H., Zsoldos, D., Brengel-Pesce, K., Grenier, J., Cleuziat, P., Lopez-Crapez, E. Lab. Invest. (2006) [Pubmed]
  14. Electrically conducting polymers can noninvasively control the shape and growth of mammalian cells. Wong, J.Y., Langer, R., Ingber, D.E. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  15. Automated in-tube solid-phase microextraction coupled with HPLC for the determination of N-nitrosamines in cell cultures. Mullett, W.M., Levsen, K., Borlak, J., Wu, J., Pawliszyn, J. Anal. Chem. (2002) [Pubmed]
  16. A facile synthesis of polypyrrole nanotubes using a template-mediated vapor deposition polymerization and the conversion to carbon nanotubes. Jang, J., Oh, J.H. Chem. Commun. (Camb.) (2004) [Pubmed]
  17. Overoxidized polypyrrole-coated carbon fiber microelectrodes for dopamine measurements with fast-scan cyclic voltammetry. Pihel, K., Walker, Q.D., Wightman, R.M. Anal. Chem. (1996) [Pubmed]
  18. Biochemistry of dinoflagellate bioluminescence: purification and characterization of dinoflagellate luciferin from Pyrocystis lunula. Dunlap, J.C., Hastings, J.W. Biochemistry (1981) [Pubmed]
  19. Surfactant-directed polypyrrole/CNT nanocables: synthesis, characterization, and enhanced electrical properties. Zhang, X., Zhang, J., Wang, R., Zhu, T., Liu, Z. Chemphyschem : a European journal of chemical physics and physical chemistry. (2004) [Pubmed]
  20. A noninterference polypyrrole glucose biosensor. Chen, C., Jiang, Y., Kan, J. Biosensors & bioelectronics. (2006) [Pubmed]
  21. Culture of human keratinocytes on polypyrrole-based conducting polymers. Ateh, D.D., Vadgama, P., Navsaria, H.A. Tissue engineering. (2006) [Pubmed]
  22. Carrier dynamics in conducting polymers: case of PF6 doped polypyrrole. Romijn, I.G., Hupkes, H.J., Martens, H.C., Brom, H.B., Mukherjee, A.K., Menon, R. Phys. Rev. Lett. (2003) [Pubmed]
  23. Composite carbon paste biosensor for phenolic derivatives based on in situ electrogenerated polypyrrole binder. Mailley, P., Cummings, E.A., Mailley, S.C., Eggins, B.R., McAdams, E., Cosnier, S. Anal. Chem. (2003) [Pubmed]
  24. Substrate-purging enzyme electrodes. Peroxidase/catalase electrodes for H2O2 with an improved upper sensing limit. Tatsuma, T., Watanabe, T., Tatsuma, S., Watanabe, T. Anal. Chem. (1994) [Pubmed]
  25. Fabrication of polypyrrole-based nanoelectrode arrays by colloidal lithography. Valsesia, A., Lisboa, P., Colpo, P., Rossi, F. Anal. Chem. (2006) [Pubmed]
  26. Clinically related protein-peptide interactions monitored in real time on novel peptide chips by surface plasmon resonance imaging. Cherif, B., Roget, A., Villiers, C.L., Calemczuk, R., Leroy, V., Marche, P.N., Livache, T., Villiers, M.B. Clin. Chem. (2006) [Pubmed]
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