Kamal, Ahmed ; Shankaraiah, Nagula ; Reddy, Ch. Ratna ; Prabhakar, S. ; Markandeya, Nagula ; Srivastava, Hemant Kumar ; Sastry, G. Narahari (2010) Synthesis of bis-1,2,3-triazolo-bridged unsymmetrical pyrrolobenzodiazepine trimers via ‘click’ chemistry and their DNA-binding studies Tetrahedron, 66 (29). pp. 5498-5506. ISSN 0040-4020
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/j.tet.2010.05.003
Abstract
New conceivable synthetic approach for the construction of nitrogen-rich 1,2,3-triazolo-pyrrolo[2,1-c][1,4]benzodiazepine (TPBD, 3a–c) trimers has been developed. The first example of a bis-1,2,3-triazolo-bridged unsymmetrical PBD trimer has been successfully synthesized by employing a CuAAC type ‘click’ chemistry protocol. This efficient route generates tri-imine functionality in a single molecule. It has been envisaged that such tri-imine functionalities could bring in efficient interaction with DNA in a sequence-selective manner in the minor groove of duplex DNA. One of the representative analogues 3c has shown improved DNA-binding ability (ΔTm23.7 °C) by thermal denaturation studies using CT-DNA and this data is also supported by molecular modeling (MD) studies.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Pyrrolobenzodiazepine Trimers; 1,2,3-Triazoles; Click Chemistry; Cycloadditions; DNA-Binding Affinity; Molecular Modeling |
| ID Code: | 108100 |
| Deposited On: | 28 Jul 2017 05:52 |
| Last Modified: | 28 Jul 2017 05:52 |
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