266
Views
0
CrossRef citations to date
0
Altmetric
Research Articles

Designing of new tetrahydro-β-carboline-based ABCG2 inhibitors using 3D-QSAR, molecular docking, and DFT tools

ORCID Icon, ORCID Icon, &
Pages 14016-14027 | Received 19 Dec 2022, Accepted 30 Jan 2023, Published online: 08 Feb 2023

References

  • Ahamad, S., Hassan, M., & Dwivedi, N. (2018). Designing of phenol-based β− carbonic anhydrase1 inhibitors through QSAR, molecular docking, and MD simulation approach. 3 Biotech, 8(5), 1–18. https://doi.org/10.1007/s13205-018-1278-z
  • Ahamad, S., Islam, A., Ahmad, F., Dwivedi, N., & Hassan, M. I. (2019). 2/3D-QSAR, molecular docking and MD simulation studies of FtsZ protein targeting benzimidazoles derivatives. Computational Biology and Chemistry, 78, 398–413.
  • Ahamad, S., Kanipakam, H., Birla, S., Ali, M. S., & Gupta, D. (2021). Screening Malaria-box compounds to identify potential inhibitors against SARS-CoV-2 Mpro, using molecular docking and dynamics simulation studies. European Journal of Pharmacology, 890, 173664.
  • Ahmad, S., Hassan, M. I., Gupta, D., Dwivedi, N., & Islam, A. (2022). Design and evaluation of pyrimidine derivatives as potent inhibitors of ABCG2, a breast cancer resistance protein. 3 Biotech, 12(9), 1–17. https://doi.org/10.1007/s13205-022-03231-1
  • Alshammari, M. M., et al. (2021). Synthesis, characterization, anticancer and in silico studies of a pyrazole-tethered thiazolidine-2, 4-dione derivative. Journal of Biomolecular Structure and Dynamics, 40(23), 13075-13082.
  • Amaro, R. E., Baudry, J., Chodera, J., Demir, Ö., McCammon, J. A., Miao, Y., & Smith, J. C. (2018). Ensemble docking in drug discovery. Biophysical Journal, 114(10), 2271–2278.
  • Arnold, M., Morgan, E., Rumgay, H., Mafra, A., Singh, D., Laversanne, M., Vignat, J., Gralow, J. R., Cardoso, F., Siesling, S., & Soerjomataram, I. (2022). Current and future burden of breast cancer: Global statistics for 2020 and 2040. Breast (Edinburgh, Scotland), 66, 15–23.
  • Attiq, N., Arshad, U., Brogi, S., Shafiq, N., Imtiaz, F., Parveen, S., Rashid, M., & Noor, N. (2022). Exploring the anti-SARS-CoV-2 main protease potential of FDA approved marine drugs using integrated machine learning templates as predictive tools. International Journal of Biological Macromolecules, 220, 1415–1428.
  • Chun, K.-H., Park, J. H., & Fan, S. (2017). Predicting and overcoming chemotherapeutic resistance in breast cancer. Translational Research in Breast Cancer, 1026, 59–104.
  • Daina, A., Michielin, O., & Zoete, V. (2017). SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Scientific Reports, 7, 42717.
  • Deppmeier, B., et al. (2002). SPARTAN 02. Wavefunction Inc.
  • Faizi, M. S. H., Alam, M. J., Haque, A., Ahmad, S., Shahid, M., & Ahmad, M. (2018). Experimental and theoretical characterization of organic salt: 2-((4-bromophenyl) amino) pyrido [1, 2-a] quinoxalin-11-ium bromide monohydrate synthesized via oxidative cyclization. Journal of Molecular Structure, 1156, 457–464. https://doi.org/10.1016/j.molstruc.2017.12.014
  • Floresta, G., Amata, E., Dichiara, M., Marrazzo, A., Salerno, L., Romeo, G., Prezzavento, O., Pittalà, V., & Rescifina, A. (2018). Identification of Potentially Potent Heme Oxygenase 1 Inhibitors through 3D‐QSAR Coupled to Scaffold‐Hopping Analysis. ChemMedChem. 13(13), 1336–1342.
  • Floresta, G., Cilibrizzi, A., Abbate, V., Spampinato, A., Zagni, C., & Rescifina, A. (2019). 3D-QSAR assisted identification of FABP4 inhibitors: An effective scaffold hopping analysis/QSAR evaluation. Bioorganic Chemistry, 84, 276–284.
  • Gribble, G. W. (1996). Pyrroles and their benzo derivatives: applications.
  • Haque, A., Al-Balushi, R. A., Al-Busaidi, I. J., Khan, M. S., & Raithby, P. R. (2018). Rise of conjugated poly-ynes and poly (metalla-ynes): from design through synthesis to structure–property relationships and applications. Chemical Reviews, 118(18), 8474–8597. https://doi.org/10.1021/acs.chemrev.8b00022
  • Haque, A., Rahman, M. A., Faizi, M. S. H., & Khan, M. S. (2018). Next Generation Antineoplastic Agents: A Review on Structurally Modified Vinblastine (VBL) Analogues. Current Medicinal Chemistry, 25(14), 1650–1662.
  • Haque, A., Xu, L., Al-Balushi, R. A., Al-Suti, M. K., Ilmi, R., Guo, Z., Khan, M. S., Wong, W.-Y., & Raithby, P. R. (2019). Cyclometallated tridentate platinum (II) arylacetylide complexes: old wine in new bottles. Chemical Society Reviews, 48(23), 5547–5563.
  • Jackson, S. M., Manolaridis, I., Kowal, J., Zechner, M., Taylor, N. M. I., Bause, M., Bauer, S., Bartholomaeus, R., Bernhardt, G., Koenig, B., Buschauer, A., Stahlberg, H., Altmann, K.-H., & Locher, K. P. (2018). Structural basis of small-molecule inhibition of human multidrug transporter ABCG2. Nature Structural & Molecular Biology, 25(4), 333–340. https://doi.org/10.1038/s41594-018-0049-1
  • Laskowski, R. A., MacArthur, M. W., Moss, D. S., & Thornton, J. M. (1993). PROCHECK: a program to check the stereochemical quality of protein structures. Journal of Applied Crystallography, 26(2), 283–291. https://doi.org/10.1107/S0021889892009944
  • Lee, S., et al. (2003). The PreADME Approach: Web-based program for rapid prediction of physico-chemical, drug absorption and drug-like properties. EuroQSAR Designing Drugs and Crop Protectants: processes, Problems and Solutions, 2003, 418–420.
  • Lipinski, C. A. (2016). Rule of five in 2015 and beyond: Target and ligand structural limitations, ligand chemistry structure and drug discovery project decisions. Advanced Drug Delivery Reviews, 101, 34–41.
  • Liu, W., Liu, X., Liu, W., Gao, Y., Wu, L., Huang, Y., Chen, H., Li, D., Zhou, L., Wang, N., Xu, Z., Jiang, X., & Zhao, Q. (2022). Discovery of novel β-carboline derivatives as selective AChE inhibitors with GSK-3β inhibitory property for the treatment of Alzheimer’s disease. European Journal of Medicinal Chemistry, 229, 114095.
  • Mohammad, I. S., He, W., & Yin, L. (2018). Understanding of human ATP binding cassette superfamily and novel multidrug resistance modulators to overcome MDR. Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie, 100, 335–348. https://doi.org/10.1016/j.biopha.2018.02.038
  • Moinul, M., Amin, S. A., Jha, T., & Gayen, S. (2022). Updated chemical scaffolds of ABCG2 inhibitors and their structure-inhibition relationships for future development. European Journal of Medicinal Chemistry, 241, 114628. https://doi.org/10.1016/j.ejmech.2022.114628
  • Mushtaque, M., Avecilla, F., Haque, A., Perwez, A., Khan, M. S., & Rizvi, M. M. A. (2017). Experimental and theoretical studies of a pyrazole-thiazolidin-2, 4-di-one hybrid. Journal of Molecular Structure, 1141, 417–427. https://doi.org/10.1016/j.molstruc.2017.03.100
  • Nakanishi, T., & Ross, D. D. (2012). Breast cancer resistance protein (BCRP/ABCG2): its role in multidrug resistance and regulation of its gene expression. Chinese Journal of Cancer, 31(2), 73–99.
  • Orlando, B. J., & Liao, M. (2020). ABCG2 transports anticancer drugs via a closed-to-open switch. Nature Communications, 11(1), 1–11. https://doi.org/10.1038/s41467-020-16155-2
  • Patel, H., Wu, Z.-X., Chen, Y., Bo, L., & Chen, Z.-S. (2021). Drug resistance: From bacteria to cancer. Molecular Biomedicine, 2(1), 1–19. https://doi.org/10.1186/s43556-021-00041-4
  • Schrödinger, L. (2012). QikProp, version 3.5.
  • Song, H., Liu, Y., Liu, Y., Wang, L., & Wang, Q. (2014). Synthesis and antiviral and fungicidal activity evaluation of β-carboline, dihydro-β-carboline, tetrahydro-β-carboline alkaloids, and their derivatives. Journal of Agricultural and Food Chemistry, 62(5), 1010–1018.
  • Spindler, A., Stefan, K., & Wiese, M. (2016). Synthesis and investigation of tetrahydro-β-carboline derivatives as inhibitors of the breast cancer resistance protein (ABCG2). Journal of Medicinal Chemistry, 59(13), 6121–6135.
  • Taylor, N. M. I., Manolaridis, I., Jackson, S. M., Kowal, J., Stahlberg, H., & Locher, K. P. (2017). Structure of the human multidrug transporter ABCG2. Nature, 546(7659), 504–509.
  • Tian, W., Chen, C., Lei, X., Zhao, J., & Liang, J. (2018). CASTp 3.0: computed atlas of surface topography of proteins. Nucleic Acids Research, 46(W1), W363–W367.
  • Wang, J., Gong, F., Liang, T., Xie, Z., Yang, Y., Cao, C., Gao, J., Lu, T., & Chen, X. (2021). A review of synthetic bioactive tetrahydro-β-carbolines: A medicinal chemistry perspective. European Journal of Medicinal Chemistry, 225, 113815.
  • Xing, X., et al. (2022). Discovery of Novel Tetrahydro-β-carboline Containing Aminopeptidase N Inhibitors as Cancer Chemosensitizers. Frontiers in Oncology, 12, 894842.

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.