- Guanine-Containing DNA Minor-Groove binders
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Solid-phase procedures have been used to prepare six di-pyrrole-containing DNA ligands that combine (guanin-9-yl)-acetyl, (guanin-7-yl)acetyl or acetyl moieties at the N-terminal end and two lysines or a (dimethylamino)propyl group at the C terminus. Inspection of their DNA-stabilizing properties by UV-monitored thermal denaturation experiments showed that the ligand incorporating the (guanin-9-yl)acetyl group and the (dimethylamino)propyl tail had the highest duplex-stabilizing effects. Wiley-VCH Verlag GmbH & Co, KGaA.
- Pulido, Daniel,Sanchez, Albert,Robles, Jordi,Pedroso, Enrique,Grandas, Anna
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- Synthesis of pyrrole-imidazole polyamide oligomers based on a copper-catalyzed cross-coupling strategy
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Pyrrole-imidazole (Py-Im) polyamides are useful tools for chemical biology and medicinal chemistry studies due to their unique binding properties to the minor groove of DNA. We developed a novel method of synthesizing Py-Im polyamide oligomers based on a Cu-catalyzed cross-coupling strategy. All four patterns of dimer fragments could be synthesized using a Cu-catalyzed Ullmann-type cross-coupling with easily prepared monomer units. Moreover, we demonstrated that pyrrole dimer, trimer, and tetramer building blocks for Py-Im polyamide synthesis were accessible by combining site selective iodination of the pyrrole/pyrrole coupling adduct.
- Shiga, Naoki,Takayanagi, Shihori,Muramoto, Risa,Murakami, Tasuku,Qin, Rui,Suzuki, Yuta,Shinohara, Ken-ichi,Kaneda, Atsushi,Nemoto, Tetsuhiro
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- METHOD FOR PRODUCING NITROGEN-CONTAINING AROMATIC AMIDE, METHOD FOR PRODUCING PYRROLE-IMIDAZOLE POLYAMIDE, AND COMPOUND
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To provide a method for producing a nitrogen-containing aromatic amide that is capable of using a monomer unit obtained under milder reaction condition and uses catalytic amide bond formation, and a method for producing a pyrrole-imidazole polyamide. [1] A method for producing a nitrogen-containing aromatic amide, including reacting a compound 1 represented by the general formula (1) and a compound 2 represented by the general formula (2) in the presence of a transition metal catalyst and a base, so as to provide a compound 3 represented by the general formula (3). [2] A method for producing a pyrrole-imidazole polyamide, including using the compound 3 obtained by the production method according to the item [1]. [3] A compound represented by the general formula (2aa), the general formula (2ab), the general formula (2ac), or the general formula (2ad).
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Paragraph 0388; 0389; 0390; 0391
(2019/04/05)
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- Synthesis of distamycin a polyamides targeting G-quadruplex DNA
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A number of amide-linked oligopyrroles based on distamycin molecules have been synthesized by solid-state methods, and their interactions with a human intramolecular G-quadruplex have been measured by a melting procedure. Several of these molecules show an enhanced ratio of quadruplex vs. duplex DNA binding compared to distamycin itself, including one with a 2,5-disubstituted pyrrole group. Quadruplex affinity increases with the number of pyrrole groups, and it is suggested that this is consistent with a mixed groove/G-quartet stacking binding mode. The Royal Society of Chemistry 2006.
- Moore, Michael J. B.,Cuenca, Francisco,Searcey, Mark,Neidle, Stephen
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p. 3479 - 3488
(2008/09/17)
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- Synthesis of N-methylpyrrole and N-methylimidazole amino acids suitable for solid-phase synthesis
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New and higher yielding synthetic routes to N-protected N-methylpyrrole and N-methylimidazole amino acids are introduced to circumvent difficulties associated with established schemes. Key steps in each synthesis include copper-mediated cross-coupling reaction to directly install a carbamate-protected 4-amine in the N-methylpyrrole derivative and effective nitration followed by a one-pot reduction/Boc protection of the amine in the synthesis of the N-Me-imidazole amino acid.
- Jaramillo, David,Liu, Qi,Aldrich-Wright, Janice,Tor, Yitzhak
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p. 8151 - 8153
(2007/10/03)
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- Alpha- haloenamine reagents
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The present invention describes immobilized haloenamine reagents, immobilized tertiary amides, methods for their preparation, and methods of use.
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- Aromatic and heteroaromatic acid halides for synthesizing polyamides
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The present invention is directed to protected amino acid halide monomers and oligomers, and to their use in the efficient sythesis of polyamides. The present invention is further directed to the use of α-haloenamine reagents, which may optionally be immobilized, for the preparation of the amino acid halides.
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- Solid phase synthesis of polyamides containing imidazole and pyrrole amino acids
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The solid phase synthesis of sequence specific DNA binding polyamides containing N-methylimidazole (Im) and N-methylpyrrole (Py) amino acids is described. Two monomer building blocks, Boc-Py-OBt ester and Boc-Im acid, are prepared on a 50 g scale without column chromatography. Using commercially available Boc-β-alanine-Pam resin, cycling protocols were optimized to afford high stepwise coupling yields (>99%). Deprotection by aminolysis affords up to 100 mg quantities of polyamide. Solid phase methodology increases both the number and complexity of minor groove binding polyamides which can be synthesized and analyzed with regard to DNA binding affinity and sequence specificity. The solid phase synthesis of a representative eight-residue polyamide is reported.
- Baird, Eldon E.,Dervan, Peter B.
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p. 6141 - 6146
(2007/10/03)
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- Design, synthesis, DNA binding, and biological activity of a series of DNA minor-groove-binding intercalating drugs
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A group of pseudopeptides, molecular combination of the natural antitumor agents distamycin or netropsin and the anilinoacridine chromophore (which is related to the synthetic antileukemic drug amsacrine) has been synthesized. Their DNA binding properties were determined and discussed in terms of their structural differences and in relation to their observed base-dependent binding. Binding data are consistent with a model in which the acridine nucleus occupies an intercalation site and the netropsin or distamycin residue resides in the DNA minor groove. Cytostatic and cytotoxic activities against a murine cell line are reported, as well as significant differences in the inhibition of DNA synthesis.
- Bailly,Pommery,Houssin,Henichart
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p. 910 - 917
(2007/10/02)
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