222
Views
0
CrossRef citations to date
0
Altmetric
Articles

Molecular encapsulation of berberine and ethidium bromide in anthraquinonecarboxamido-β-cyclodextrin conjugate: supramolecular association with DNA duplex and G-quadruplexes

, , , &
Pages 542-558 | Received 21 Aug 2020, Accepted 20 Mar 2021, Published online: 07 Apr 2021

References

  • Comini, L. R.; Montoya, S. C. N.; Páez, P. L.; Argüello, G. A.; Albesa, I.; Cabrera, J. L. Antibacterial Activity of Anthraquinone Derivatives from Heterophyllaea pustulata (Rubiaceae). J. Photochem. Photobiol. B 2011, 102, 108–114. DOI: 10.1016/j.jphotobiol.2010.09.009.
  • Oz, G. D. –M.; Miranda, I. L.; Sartori, S. K.; de Rezende, D. C.; Diaz, M. A. N. Anthraquinones: An Overview, 2018, Studies in Natural Products Chemistry. In Studies in Natural Products Chemistry, Elsevier, USA, 2018; pp. 313–338.
  • Thiele, C.; Auerbach, D.; Jung, G.; Wenz, G. Inclusion of Chemotherapeutic Agents in Substituted β-Cyclodextrin Derivatives. J. Incl. Phenom. Macrocycl. Chem. 2011, 69, 303–307. DOI: 10.1007/s10847-010-9741-4.
  • Chien, S.-C.; Wu, Y.-C.; Chen, Z.-W.; Yang, W.-C. Naturally Occurring Anthraquinones: Chemistry and Therapeutic Potential in Autoimmune Diabetes. Evid. Based Complement. Alternat. Med. 2015, 2015, 357357. DOI: 10.1155/2015/357357.
  • van Os, F. H. Some Aspects of the Pharmacology of Anthraquinone Drugs. Pharmacology 1976, 14, 18–29. DOI: 10.1159/000136683.
  • Oliveira, R. C. S.; Corrêa, R. J.; Teixeira, R. S. P.; Queiroz, D. D.; Souza, R. S.; Garden, S. J.; Lucas, N. C.; Pereira, M. D.; Forero, J. S. B.; Romani, E. C.; Ribeiro, E. S. Silica Nanoparticles Doped with Anthraquinone for Lung Cancer Phototherapy. J. Photochem. Photobiol. B 2016, 165, 1–9. DOI: 10.1016/j.jphotobiol.2016.10.008.
  • Jiang, H.; Sun, H.; Zhang, S.; Hua, R.; Xu, Y.; Jin, S.; Gong, H.; Li, L. NMR Investigations of Inclusion Complexes between β-Cyclodextrin and Naphthalene/Anthraquinone Derivatives. J. Incl. Phenom. Macrocycl. Chem. 2007, 58, 133–138. DOI: 10.1007/s10847-006-9135-9.
  • Malik, E. M.; Müller, C. E. Anthraquinones as Pharmacological Tools and Drugs. Med. Res. Rev. 2016, 36, 705–748. DOI: 10.1002/med.21391.
  • Huang, Q.; Lu, G.; Shen, H. M.; Chung, M. C.; Ong, C. N. Anti-Cancer Properties of Anthraquinones from Rhubarb. Med. Res. Rev. 2007, 27, 609–630. DOI: 10.1002/med.20094.
  • Jelassi, B.; Anchelin, M.; Chamouton, J.; Cayuela, M. L.; Clarysse, L.; Li, J.; Goré, J.; Jiang, L. H.; Roger, S. Anthraquinone Emodin Inhibits Human Cancer Cell Invasiveness by Antagonizing P2X7 Receptors. Carcinogenesis 2013, 34, 1487–1496. DOI: 10.1093/carcin/bgt099.
  • Adhikari, A.; Mahar, K. S. DNA Targeted Anthraquinone Derivatives: An Important Anticancer Agents. Int. J. Pharm. Pharm. Sci. 2016, 8, 17–25.
  • Tian, W.; Wang, C.; Li, D.; Hou, H. Novel Anthraquinone Compounds as Anticancer Agents and Their Potential Mechanism. Future Med. Chem. 2020, 12, 627–644. DOI: 10.4155/fmc-2019-0322.
  • Zagotto, G.; Sissi, C.; Lucatello, L.; Pivetta, C.; Cadamuro, S. A.; Fox, K. R.; Neidle, S.; Palumbo, M. Aminoacyl-Anthraquinone Conjugates as Telomerase Inhibitors: Synthesis, Biophysical and Biological Evaluation. J. Med. Chem. 2008, 51, 5566–5574. DOI: 10.1021/jm800160v.
  • Gholivand, M. B.; Kashanian, S.; Peyman, H.; Roshanfekr, H. DNA-Binding Study of Anthraquinone Derivatives Using Chemometrics Methods. Eur. J. Med. Chem. 2011, 46, 2630–2638. DOI: 10.1016/j.ejmech.2011.03.034.
  • Breslin, D. T.; Yu, C.; Ly, D.; Schuster, G. B. Structural Modification Changes the DNA Binding Mode of Cation-Substituted Anthraquinone Photonucleases: Association by Intercalation or Minor Groove Binding Determines the DNA Cleavage efficiency. Biochemistry 1997, 36, 10463–10473. DOI: 10.1021/bi9702750.
  • Yao, Q.; Lin, M. T.; Lan, Q. H.; Huang, Z. W.; Zheng, Y. W.; Jiang, X.; Zhu, Y. D.; Kou, L.; Xu, H. L.; Zhao, Y. Z. In Vitro and In Vivo Evaluation of Didymin Cyclodextrin Inclusion Complexes: Characterization and Chemosensitization Activity. Drug Deliv. 2020, 27, 54–65. DOI: 10.1080/10717544.2019.1704941.
  • Suganthi, S.; Sivaraj, R.; Enoch, I. V. M. V. Molecular Encapsulation of Berberine by a Modified β-Cyclodextrin and Binding of Host: Guest Complex to G-Quadruplex DNA. Nucleosides Nucleotides Nucleic Acids. 2019, 38, 858–873. DOI: 10.1080/15257770.2019.1618469.
  • Huang, K.; Jiang, L.; Li, H.; Ye, D.; Zhou, L. Development of Anthraquinone Analogues as Phosphoglycerate Mutase I Inhibitors. Molecules 2019, 24, 845. DOI: 10.3390/molecules24050845.
  • Koceva-Chyła, A.; Jedrzejczak, M.; Skierski, J.; Kania, K.; Jóźwiak, Z. Mechanisms of Induction of Apoptosis by Anthraquinone Anticancer Drugs Aclarubicin and Mitoxantrone in Comparison with Doxorubicin: Relation to Drug Cytotoxicity and Caspase-3 Activation. Apoptosis 2005, 10, 1497–1514. DOI: 10.1007/s10495-005-1540-9.
  • Tsai, S.-Y.; Kuo, S.-C.; Lin, S.-Y. Physicochemical Characterization of 9,10-Anthraquinone 2-Carboxylic Acid. J. Pharm. Sci. 1993, 82, 1250–1254. DOI: 10.1002/jps.2600821213.
  • Park, J. G.; Kim, S. C.; Kim, Y. H.; Yang, W. S.; Kim, Y.; Hong, S.; Kim, K. H.; Yoo, B. C.; Kim, S. H.; Kim, J. H.; Cho, J. Y. Anti-Inflammatory and Antinociceptive Activities of Anthraquinone-2-Carboxylic Acid. Mediators Inflamm. 2016, 2016, 1903849. DOI: 10.1155/2016/1903849.
  • Lakowicz, J. R. Principles of Fluorescence Spectroscopy, 3rd ed.; Springer Nature, Switzerland, 2006.
  • Mostofa, A. R.; Kundan, S.; Sivaprasad, M. Fluorescence Modulation of Excited State Intramolecular Proton Transfer (ESIPT) Probe 3-Formyl-4-hydroxybenzoic Acid Encapsulated in the Protein Binding Domain of Serum Albumins: A Combined Spectroscopic and Molecular Docking Study. J. Biomol. Struct. Dyn. 2019, 37, 4737–4746. DOI: 10.1080/07391102.2018.1559764..
  • Yousuf, S.; Enoch, I. V. M. V.; Selvakumar, P. M.; Dhanaraj, P. Loading of Chromenones on Superparamagnetic Iron Oxide-Modified Dextran Core–Shell Nanoparticles: Openness to Bind to β-Cyclodextrin and DNA. New J. Chem. 2015, 39, 7879–7888. DOI: 10.1039/C5NJ00921A.
  • Yousuf, S.; Natesan, S.; Enoch, I. V. M. V. Chemico-Biological Interaction of Etravirine and Its β-Cyclodextrin Complex with Macromolecular Targets. J. Biomol. Struct. Dyn. 2017, 35, 1006–1019. DOI: 10.1080/07391102.2016.1166987.
  • Vardevanyan, P. O.; Shahinyan, M. A.; Antonyan, A. P.; Parsadanyan, M. A.; Minasyants, M. V. Spectral Characteristics of DNA-EtBr and DNA-MB Complexes. J. Biomol. Struct. Dyn. 2015, 33, 95–95. DOI: 10.1080/07391102.2015.1032778.
  • Hazra, S.; Hossain, M.; Kumar, G. S. Binding of Isoquinoline Alkaloids Berberine, Palmatine and Coralyne to Hemoglobin: Structural and Thermodynamic Characterization Studies. Mol. Biosyst. 2013, 9, 143–153. DOI: 10.1039/C2MB25345C.
  • Jia, B.; Li, Y.; Wang, D.; Duan, R. Study on the Interaction of β-Cyclodextrin and Berberine Hydrochloride and Its Analytical Application. PLoS One. 2014, 9, e95498. DOI: 10.1371/journal.pone.0095498.
  • Yang, X.; Zhu, Y.; Liu, P.; He, L.; Li, Q.; Wang, Q.; Wang, K.; Huang, J.; Liu, J. G. Quadruplex Fluorescence Quenching Ability: A Simple and Efficient Strategy to Design a Single-Labeled DNA Probe. Anal. Methods 2012, 4, 895–897. DOI: 10.1039/c2ay25034a.
  • Yousuf, S.; Enoch, I. V. M. V.; Paulraj, M. S.; Dhanaraj, P. Chromenone-Conjugated Magnetic Iron Oxide Nanoparticles. Toward Conveyable DNA Binders. Colloids Surf. B Biointerfaces 2015, 135, 448–457. DOI: 10.1016/j.colsurfb.2015.07.049.
  • Yuan, L.; Tian, T.; Chen, Y.; Yan, S.; Xing, X.; Zhang, Z.; Zhai, Q.; Xu, L.; Wang, S.; Weng, X.; et al. Existence of G-Quadruplex Structures in Promoter Region of Oncogenes Confirmed by G-Quadruplex DNA Cross-Linking Strategy. Sci. Rep. 2013, 3, 1811. DOI: 10.1038/srep01811.
  • Phan, A. T.; Kuryavyi, V. V.; Burge, S.; Neidle, S.; Patel, D. J. Structure of an Unprecedented G-Quadruplex Scaffold in the Human c-Kit Promoter. J. Am. Chem. Soc. 2007, 129, 4386–4392. DOI: 10.1021/ja068739h.
  • Yang, D.; Hurley, L. H. Structure of the Biologically Relevant G-Quadruplex in the c-Myc Promoter. Nucleosides Nucleotides Nucleic Acids 2006, 25, 951–968. DOI: 10.1080/15257770600809913.
  • Parkinson, G. N.; Lee, M. P. H.; Neidle, S. Crystal Structure of Parallel Quadruplexes from Human Telomeric DNA. Nature 2002, 417, 876–880. DOI: 10.1038/nature755.
  • Sun, X.; Cao, E.; He, Y.; Qin, J. Fluorescence Studies on the Interaction of Ethidium Bromide with Duplex. Sci. China Ser. B Chem. 1999, 42, 62–69. DOI: 10.1007/BF02883038.
  • Machireddy, B.; Sullivan, H. J.; Wu, C. Binding of BRACO19 to a Telomeric G-Quadruplex DNA Probed by All-Atom Molecular Dynamics Simulations with Explicit Solvent. Molecules 2019, 24, 1010. DOI: 10.3390/molecules24061010.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.