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Chemical Compound Review:

Methylpyrrole 1-methylpyrrole

Synonyms: SureCN1381, PubChem10822, CCRIS 2934, M78801_ALDRICH, ACMC-20aj04, ...

Dasgupta, D. et al., Li, H. et al., Fossé, P. et al., Marques, M.A. et al., Hiraku, Y. et al., et al.

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Disease relevance of NSC 65440

Investigation of non-covalent complexes of HIV-1 promoter DNA and polyamides containing N-methylpyrrole by electrospray ionization mass spectrometry [1].
Streptomyces flavopersicus NRRL 2820 (synonym: Streptomyces netropsis DSM40093) is resistant to the N-methylpyrrole-containing oligopeptide antibiotic netropsin [2].

High impact information on NSC 65440

The discrimination of the four Watson-Crick base pairs by minor groove DNA-binding polyamides have been attributed to the specificity of three five-membered aromatic amino acid subunits, 1-methyl-1H-imidazole (Im), 1-methyl-1H-pyrrole (Py), and 3-hydroxy-1H-pyrrole (Hp) paired four different ways [3].
Gene silencing was examined by sequence-specific alkylation of DNA by N-methylpyrrole (Py)-N-methylimidazole (Im) hairpin polyamides [4].
Synthetic polyamides composed of three types of aromatic amino acids, N-methylimidazole (Im), N-methylpyrrole (Py) and N-methyl-3-hydroxypyrrole (Hp) bind specific DNA sequences as antiparallel dimers in the minor groove [5].
Electrospray ionization mass spectrometry (ESI-MS) was used to investigate noncovalent complexes formed between four novel polyamides containing N-methylpyrrole (Py) and N-methylimidazole (Im), and human telomeric DNA [6].
The apoptotic and cytotoxic activities against several tumor cell lines are reported and discussed in terms of their structural differences in relation to both the number of N-methylpyrrole rings and the type of the alkylating unit tethered to the oligopeptidic frame [7].

Biological context of NSC 65440

A binary code has been developed to correlate DNA sequence with side-by-side pairings between N-methylpyrrole (Py) and N-methylimidazole (Im) carboxamides in the DNA minor groove [8].
Eight novel polyamides containing N-methylpyrrole were designed to target the sequence (5'-CTGCATATAAGCAG-3'/5'-CTGCTTATATGCAG-3') of the TATA box element of the HIV-1 promoter DNA [1].

Associations of NSC 65440 with other chemical compounds

Electric linear dichroism spectroscopy reveals that MePyGA intercalates its acridine chromophore between DNA base pairs with a preference for GC-rich sequences, whereas both its structural analogue lacking the N-methylpyrrole unit and amsacrine intercalate into DNA without any strong sequence preference [9].
Two synthetic analogues of distamycin (Dst), PPA and PAP, containing a saturated beta-alanine moiety substituting for an N-methylpyrrole chromophore were studied for their interactions with the double-stranded alternating copolymer poly(dA-dT).poly(dA-dt) [abbreviated as poly(dA-dT)], with UV absorption and circular dichroism (CD) spectroscopy [10].
Two structurally related compounds, methylimidazole and methylpyrrole, were not olfactory toxicants, suggesting that a reactive intermediate generated in the course of metabolizing methimazole to an S-oxide is the olfactory toxic species [11].
Internal side-by-side pairings of the aromatic amino acid residues 1-methyl-1H-pyrrole (Py), 1-methyl-1H-imidazole (Im), and 3-hydroxy-1-methyl-1H-pyrrole (Hp) confer the ability to distinguish between all four Watson-Crick base pairs in the minor groove of B-form DNA [12].

Gene context of NSC 65440

We investigated the amplification of bleomycin-induced DNA cleavage by synthetic triamides containing N-methylpyrrole (Py) and/or N-methylimidazole (Im), PyPyPy, PyPyIm, PyImPy, and PyImIm, using 32P-labeled DNA fragments obtained from the human c-Ha-ras-1 and p53 genes [13].

References

Investigation of non-covalent complexes of HIV-1 promoter DNA and polyamides containing N-methylpyrrole by electrospray ionization mass spectrometry. Li, H., Yuan, G. Rapid Commun. Mass Spectrom. (2006) [Pubmed]
Cloning of the netropsin resistance genes from Streptomyces flavopersicus NRRL 2820. Stumpp, T., Himbert, S., Altenbuchner, J. J. Basic Microbiol. (2005) [Pubmed]
Expanding the repertoire of heterocycle ring pairs for programmable minor groove DNA recognition. Marques, M.A., Doss, R.M., Foister, S., Dervan, P.B. J. Am. Chem. Soc. (2004) [Pubmed]
Sequence-specific gene silencing in mammalian cells by alkylating pyrrole-imidazole polyamides. Shinohara, K., Narita, A., Oyoshi, T., Bando, T., Teraoka, H., Sugiyama, H. J. Am. Chem. Soc. (2004) [Pubmed]
Structural effects of DNA sequence on T.A recognition by hydroxypyrrole/pyrrole pairs in the minor groove. Kielkopf, C.L., Bremer, R.E., White, S., Szewczyk, J.W., Turner, J.M., Baird, E.E., Dervan, P.B., Rees, D.C. J. Mol. Biol. (2000) [Pubmed]
Analysis of noncovalent complexes between human telomeric DNA and polyamides containing N-methylpyrrole and N-methylimidazole by using electrospray ionization mass spectrometry. Zhou, J., Yuan, G. Chemistry (Weinheim an der Bergstrasse, Germany) (2005) [Pubmed]
Design, synthesis, and biological evaluation of hybrid molecules containing alpha-methylene-gamma-butyrolactones and polypyrrole minor groove binders. Baraldi, P.G., Del Carmen Nunez, M., Tabrizi, M.A., De Clercq, E., Balzarini, J., Bermejo, J., Estévez, F., Romagnoli, R. J. Med. Chem. (2004) [Pubmed]
On the pairing rules for recognition in the minor groove of DNA by pyrrole-imidazole polyamides. White, S., Baird, E.E., Dervan, P.B. Chem. Biol. (1997) [Pubmed]
Stimulation of site-specific topoisomerase II-mediated DNA cleavage by an N-methylpyrrolecarboxamide-anilinoacridine conjugate: relation to DNA binding. Fossé, P., René, B., Saucier, J.M., Hénichart, J.P., Waring, M.J., Colson, P., Houssier, C., Bailly, C. Biochemistry (1994) [Pubmed]
Interaction of synthetic analogues of distamycin with poly(dA-dT): role of the conjugated N-methylpyrrole system. Dasgupta, D., Parrack, P., Sasisekharan, V. Biochemistry (1987) [Pubmed]
Olfactory toxicity of methimazole: dose-response and structure-activity studies and characterization of flavin-containing monooxygenase activity in the Long-Evans rat olfactory mucosa. Genter, M.B., Deamer, N.J., Blake, B.L., Wesley, D.S., Levi, P.E. Toxicologic pathology. (1995) [Pubmed]
DNA minor-groove recognition by 3-methylthiophene/pyrrole pair. Doss, R.M., Marques, M.A., Foister, S., Dervan, P.B. Chem. Biodivers. (2004) [Pubmed]
Amplification of bleomycin-induced DNA cleavage at cytosine residues 3' to GGG sequences by pyrrole triamide. Hiraku, Y., Oikawa, S., Kuroki, K., Sugiyama, H., Saito, I., Kawanishi, S. Biochem. Pharmacol. (2001) [Pubmed]

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