Next Generation Hairpin Polyamides with (R)-3,4-Diaminobutyric Acid Turn Unit Export

@article{citeulike:3019675, abstract = {Abstract: The characterization of a new class of pyrroleimidazole hairpin polyamides with ²-amino-³-turn units for recognition of the DNA minor groove is reported. A library of eight hairpins containing (R)- and (S)-3,4-diaminobutyric acid (²-amino-³-turn) has been synthesized, and the impact of the molecules on DNA-duplex stabilization was studied for comparison with the parent ³-aminobutyric acid (³-turn) and standard (R)-2,4-diaminobutyric acid (±-amino-³-turn)-linked eight-ring polyamides. For some, but not all, sequence compositions, melting temperature analyses have revealed that both enantiomeric forms of the ²-amino-³-turn increase the DNA-binding affinity of polyamides relative to the (R)-±-amino-³-turn. The (R)-²-amine residue may be an attractive alternative for constructing hairpin polyamide conjugates. Biological assays have shown that (R)-²-amino-³-turn hairpins are able to inhibit androgen receptor-mediated gene expression in cell culture similar to hairpins bearing the standard (R)-±-amino-³-turn, from which we infer they are cell-permeable.}, address = {Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125}, author = {Dose, Christian and Farkas, Michelle E. and Chenoweth, David M. and Dervan, Peter B.}, citeulike-article-id = {3019675}, citeulike-linkout-0 = {http://dx.doi.org/10.1021/ja800888d}, citeulike-linkout-1 = {http://pubs.acs.org/doi/abs/10.1021/ja800888d}, day = {28}, doi = {10.1021/ja800888d}, journal = {J. Am. Chem. Soc.}, keywords = {dna, domain, gal4, polyamide}, month = {May}, number = {21}, pages = {6859--6866}, posted-at = {2008-07-18 22:15:51}, priority = {2}, title = {Next Generation Hairpin Polyamides with (R)-3,4-Diaminobutyric Acid Turn Unit}, url = {http://dx.doi.org/10.1021/ja800888d}, volume = {130}, year = {2008} }

TY - JOUR ID - citeulike:3019675 L3 - citeulike-article-id:3019675 N2 - Abstract: The characterization of a new class of pyrroleimidazole hairpin polyamides with ²-amino-³-turn units for recognition of the DNA minor groove is reported. A library of eight hairpins containing (R)- and (S)-3,4-diaminobutyric acid (²-amino-³-turn) has been synthesized, and the impact of the molecules on DNA-duplex stabilization was studied for comparison with the parent ³-aminobutyric acid (³-turn) and standard (R)-2,4-diaminobutyric acid (±-amino-³-turn)-linked eight-ring polyamides. For some, but not all, sequence compositions, melting temperature analyses have revealed that both enantiomeric forms of the ²-amino-³-turn increase the DNA-binding affinity of polyamides relative to the (R)-±-amino-³-turn. The (R)-²-amine residue may be an attractive alternative for constructing hairpin polyamide conjugates. Biological assays have shown that (R)-²-amino-³-turn hairpins are able to inhibit androgen receptor-mediated gene expression in cell culture similar to hairpins bearing the standard (R)-±-amino-³-turn, from which we infer they are cell-permeable. IS - 21 JF - J. Am. Chem. Soc. AD - Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125 EP - 6866 TI - Next Generation Hairpin Polyamides with (R)-3,4-Diaminobutyric Acid Turn Unit VL - 130 SP - 6859 KW - dna KW - domain KW - gal4 KW - polyamide AU - Dose, Christian AU - Farkas, Michelle AU - Chenoweth, David AU - Dervan, Peter PY - 2008/05/28/ UR - http://dx.doi.org/10.1021/ja800888d ER -