162085-97-4Relevant academic research and scientific papers
4-Methyltrityl-Protected Pyrrole and Imidazole Building Blocks for Solid Phase Synthesis of DNA-Binding Polyamides
Heinrich, Benedikt,Vázquez, Olalla
, p. 533 - 536 (2020/01/31)
DNA-binding polyamides are synthetic oligomers of pyrrole/imidazole units with high specificity and affinity for double-stranded DNA. To increase their synthetic diversity, we report a mild methodology based on 4-methyltrityl (Mtt) solid phase peptide synthesis (SPPS), whose building blocks are more accessible than the standard Fmoc and Boc SPPS ones. We demonstrate the robustness of the approach by preparing and studying a hairpin with all precursors. Importantly, our strategy is orthogonal and compatible with sensitive molecules and could be readily automated.
Synthesis of DNA-sequence-selective hairpin polyamide platinum complexes
Taleb, Robin I.,Jaramillo, David,Wheate, Niai J.,Aldrich-Wright, Janice R.
, p. 3177 - 3186 (2008/02/05)
Two DNA-sequence-selective hairpin polyamide platinum(II) complexes, containing pyrrole and imidazole heterocyclic rings, have been synthesised by different methods. A six-ring complex, selective for (A/T)GGG-(A/T) DNA sequences, was made by using solid-phase synthesis, whilst an eight-ring complex, selective for (A/ T)CCTG(A/T) DNA sequences, was made by utilising standard wet chemistry. Solid-phase synthesis resulted in a significantly higher yield, required less purification and is more efficient than the wet synthesis; as such, it is the preferred method for further work. The metal complexes were characterised by 1H and 195Pt NMR spectroscopy and ESI mass spectrometry. The two compounds provide a foundation for the synthesis of more complex molecules containing multiple hairpins and/or platinum groups.
OLIGOHETEROAROMATIC LUMINISCENT ASSEMBLIES AS HIGH-AFFINITY DNA SEQUENCE-DIRECTED LIGANDS
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Page/Page column 87, (2010/11/27)
The present invention provides a novel class of oligoheteroaromatic assemblies with luminescence characteristics and composition based on integrated polyheterocyclic polyamide oligomers of multiple nitrogen-containing heteroaromatic of the general formula (I) This novel class of compounds of the present invention is capable of binding to targeted DNA sequence in the minor groove, and thus is useful for genomics applications. In particular, the compounds of the invention binds to the DNA at a binding stoichiometry of 2: 1 ternary complexation with very high affinity and sequence selectivity.
Synthesis and cytotoxicity evaluation of novel C7-c7, C7-N3 and N3-N3 dimers of 1-chloromethyl-5-hydroxy-1,2-dihydro-3H-benzo[e]indole (seco-CBI) with pyrrole and imidazole polyamide conjugates.
Kumar, Rohtash,Lown, J William
, p. 2630 - 2647 (2007/10/03)
The C7-C7, C7-N3 and N3-N3 dimers of 1-chloromethyl-5-hydroxy-1,2-dihydro-3H-benzo[e]indole (seco-CBI) with pyrrole and imidazole polyamides were synthesized and preliminary anti-cancer evaluation carried out by NCI against three types of cancer cells.
SYNTHESIS OF DESIGNED FUNCTIONAL MODELS OF BLEOMYCIN INCORPORATING IMIDAZOLE - CONTAINING LEXITROPSINS AS NOVEL DNA RECOGNITION SITES
Huang, Liren,Lown, J. William
, p. 1181 - 1196 (2007/10/02)
Synthesis and characterization of compounds 1a-d, designed functional models for the antitumor antibiotic bleomycin, in which AMPHIS serves as the metal complexing subunit, chiral 1,2-trans-disubstituted cyclopropane as linkers and imidazole-containing lexitropsins as DNA sequence selective binding sites, are described.
