2873-62-3Relevant academic research and scientific papers
Benzobis(imidazolium)-cucurbit[8]uril complexes for binding and sensing aromatic compounds in aqueous solution
Biedermann, Frank,Rauwald, Urs,Cziferszky, Monika,Williams, Kyle A.,Gann, Lauren D.,Guo, Bi Y.,Urbach, Adam R.,Bielawski, Christopher W.,Scherman, Oren A.
, p. 13716 - 13722 (2010)
The utilities of benzobis(imidazolium) salts (BBIs) as stable and fluorescent components of supramolecular assemblies involving the macrocyclic host, cucurbit[8]uril (CB[8]), are described. CB[8] has the unusual ability to bind tightly and selectively to
Facile synthesis of benzobisimidazole and bibenzimidazole-based bisnitriles as potential precursors for DNA minor groove binders
Farahat, Abdelbasset A.,Iwamoto, Satori,Roche, Michael,Boykin, David W.
, p. 2280 - 2286 (2021/08/16)
The synthesis of bisnitrile derivatives of benzobisimidazole and bibenzimidazole in a good yield is described in detail for the first time. Nucleophilic substitution of 1,5-difluoro-2,4-dinitrobenzene using different amines produced the intermediate diami
Engineered modular heterocyclic-diamidines for sequence-specific recognition of mixed AT/GC base pairs at the DNA minor groove
Boykin, David W.,Farahat, Abdelbasset A.,Guo, Pu,Paul, Ananya,Wilson, W. David
, p. 15849 - 15861 (2021/12/30)
This report describes a breakthrough in a project to design minor groove binders to recognize any sequence of DNA. A key goal is to invent synthetic chemistry for compound preparation to recognize an adjacent GG sequence that has been difficult to target.
Inhibitors of topoisomerase II based on the benzodiimidazole and dipyrroloimidazobenzimidazole ring systems: Controlling DT-diaphorase reductive inactivation with steric bulk
Schulz, William G.,Skibo, Edward B.
, p. 629 - 638 (2007/10/03)
Described herein are the synthesis, cytotoxic properties, and topoisomerase II inhibition assays of benzodiimidazole and dipyrroloimidazobenzimidazole structural variants of the pyrrolo[1,2- a]benzimidazole or APBI ring system. These ring variants were designed to inhibit topoisomerase II, much as the APBIs are able to do. Since only the quinone form of the APBIs can intercalate DNA, two-electron reduction to the hydroquinone by DT-diaphorase is known to deactivate these compounds. Indeed, the APBIs possess a high inverse correlation with the cellular concentration of DT-diaphorase. Therefore one feature of the ABPI structural variants is the excessive bulk about the quinone ring, which was predicted to diminish DT-diaphorase substrate activity. Another feature is the presence of one or two alkylating centers, which would permit alkylation of DNA and/or topoisomerase II. Inhibition assays for topoisomerase II-mediated relaxation of supercoiled DNA indicate that the benzodiimidazole and dipyrrolo- imidazobenzimidazole quinone ring systems are catalytic inhibitors of topoisomerase II. Both quinone systems exhibit cytotoxicity perhaps due to the lack of inactivation by DT-diaphorase as well as topoisomerase II inhibition. One quinone displayed the novel feature of cytotoxicity selectively against melanoma cell lines. In conclusion, the benzodiimidazole and dipyrroloimid-azobenzimidazole quinone ring systems will be subjected to future analogue development and structure-activity studies.
