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      Novel Fe II and Co II Complexes of Natural Product Tryptanthrin: Synthesis and Binding with G-Quadruplex DNA

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          Abstract

          Tryptanthrin is one of the most important members of indoloquinoline alkaloids. We obtained this alkaloid from Isatis. Two novel Fe II and Co II complexes of tryptanthrin were first synthesized. Single-crystal X-ray diffraction analyses show that these complexes display distorted four-coordinated tetrahedron geometry via two heterocyclic nitrogen and oxygen atoms from tryptanthrin ligand. Binding with G-quadruplex DNA properties revealed that both complexes were found to exhibit significant interaction with G-quadruplex DNA. This study may potentially serve as the basis of future rational design of metal-based drugs from natural products that target the G-quadruplex DNA.

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          Interaction of metal complexes with G-quadruplex DNA.

          Ramon Vilar, Christos Georgiades, Kogularamanan Suntharalingam … (2010)
          Guanine-rich sequences of DNA can assemble into tetrastranded structures known as G-quadruplexes. It has been suggested that these secondary DNA structures could be involved in the regulation of several key biological processes. In the human genome, guanine-rich sequences with the potential to form G-quadruplexes exist in the telomere as well as in promoter regions of certain oncogenes. The identification of these sequences as novel targets for the development of anticancer drugs has sparked great interest in the design of molecules that can interact with quadruplex DNA. While most reported quadruplex DNA binders are based on purely organic templates, numerous metal complexes have more recently been shown to interact effectively with this DNA secondary structure. This Review provides an overview of the important roles that metal complexes can play as quadruplex DNA binding molecules, highlighting the unique properties metals can confer to these molecules.
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            Quadruplex structure of Oxytricha telomeric DNA oligonucleotides.

            PETER SMITH, J Feigon (1992)
            The telomeres of most eukaryotes contain a repeating G-rich sequence with the consensus d(T/A)1-4G1-8, of which 12-16 bases form a 3' single-strand overhang beyond the telomeric duplex. It has been proposed that these G-rich oligonucleotides associate to form four-stranded structures from one, two or four individual strands and that these structures may be relevant in vivo. The proposed structures contain Hoogsteen base-paired G-quartets, precedent for which has been in the literature for many years. Here we use 1H NMR spectroscopy to study the conformations of the DNA oligonucleotides d(G4T4G4) (Oxy-1.5) and d(G4T4G4T4G4T4G4) (Oxy-3.5) which contain the Oxytricha telomere repeat (T4G4). We find that these molecules fold to form a symmetrical bimolecular and an intramolecular quadruplex, respectively. Both structures have four G-quartets formed from nucleotides that are alternately syn and anti along each strand. This arrangement differs from earlier models in which the strands are alternately all syn or all anti. The T4 loops in Oxy-1.5 are on opposite ends of the quadruplex and loop diagonally across the G-quartet, resulting in adjacent strands being alternately parallel and antiparallel.
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              Trisubstituted isoalloxazines as a new class of G-quadruplex binding ligands: small molecule regulation of c-kit oncogene expression.

              Mallesham Bejugam, Sven Sewitz, Pravin S. Shirude … (2007)
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                Author and article information

                Journal
                Journal ID (nlm-ta): Bioinorg Chem Appl
                Journal ID (iso-abbrev): Bioinorg Chem Appl
                Journal ID (publisher-id): BCA
                Title: Bioinorganic Chemistry and Applications
                Publisher: Hindawi Publishing Corporation
                ISSN (Print): 1565-3633
                ISSN (Electronic): 1687-479X
                Publication date (Print): 2016
                Publication date (Electronic): 6 September 2016
                Volume: 2016
                Electronic Location Identifier: 5075847
                Affiliations
                1College of Pharmacy of Guangxi University of Chinese Medicine, Nanning, Guangxi 530299, China
                2Guangxi Key Laboratory for Agricultural Resources Chemistry and Efficient Utilization (Cultivation Base), Yulin Normal University, Yulin, Guangxi 537000, China
                3The Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, Guangxi Normal University, Guilin, Guangxi 541004, China
                Author notes
                *Ming-xiong Tan: tanmx00@ 123456163.com

                Academic Editor: Zhe-Sheng Chen

                Author information
                http://orcid.org/0000-0002-7474-6281
                Article
                DOI: 10.1155/2016/5075847
                PMC ID: 5029049
                SO-VID: 7b169934-8785-4e3a-bec7-864e79a17dc8
                Copyright © Copyright © 2016 Yi-ning Zhong et al.
                License:

                This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

                History
                Date received : 18 May 2016
                Date revision received : 12 July 2016
                Date accepted : 27 July 2016
                Funding
                Funded by: National Natural Science Foundation of China
                Award ID: 21261025
                Funded by: Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Education of China
                Award ID: CMEMR2011-09
                Award ID: CMEMR2014-B08
                Funded by: Key Foundation Project of Colleges and Universities in Guangxi
                Award ID: ZD2014108
                Funded by: Innovative Team & Outstanding Talent Program of Colleges and Universities in Guangxi, Science and Technology Research Projects of Guangxi
                Award ID: 1346008-4
                Funded by: Natural Science Foundation of Guangxi
                Categories
                Subject: Research Article

                ScienceOpen disciplines: Biochemistry
                Data availability:
                ScienceOpen disciplines: Biochemistry

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