Antibreast cancer activities of phytochemicals from Anonna muricata using computer-aided drug design (CADD) approach
-
Misbaudeen Abdul-Hammed
,
Ibrahim Olaide Adedotun
Abstract
Antibreast cancer activities of 131 phytochemicals from Annona muricata (Soursop) were investigated against human placental aromatase (PDB ID: 3S7S), a prominent target receptor in breast cancer therapy using computer aided-drug design approach. An antibreast cancer drug (tamoxifen) was used for comparison. The result of this work flourishes caffeoquinic acid (−8.4 kcal/mol), roseoside (−8.3 kcal/mol), chlorogenic acid (−8.2 kcal/mol), feruloylglycoside (−8.1 kcal/mol), citroside A (−8.0 kcal/mol), and coreximine (−7.8 kcal/mol), as probable inhibitors of human placental aromatase. This is due to their excellent binding affinities (ΔG), coupled with outstanding druglike, absorption, distribution, metabolism, excretion, and toxicity profiles, bioavailability and oral-bioavailability properties, and the interactions of important residues with the active pocket of human placental aromatase. All the results obtained were similar to that of the standards tamoxifen (−8.0 kcal/mol) but could be better when optimized. Thus, lead optimization, molecular dynamics, and in vivo investigations are thereby recommended on the identified potent compounds in the quest of developing new therapeutic agents against breast cancer.
Acknowledgments
The contributions of the members of the Computational-biophysical and Drug-Design Laboratory, Department of Pure and Applied Chemistry, Ladoke Akintola University of Technology, LAUTECH, Ogbomoso, Oyo State, Nigeria to the success of this research is duly acknowledged.
-
Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
-
Research funding: The authors received no financial aid for this research.
-
Conflict of interest statement: The authors declared no conflicts of interest to the authorship, research work, and/or publication of this work.
References
1. Sung, H, Ferlay, J, Siegel, RL, Laversanne, M, Soerjomataram, I, Ahmedin, J, et al.. Global cancer statistics 2020: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA A Cancer J Clin 2021;71:209–49, https://doi.org/10.3322/caac.21660.Search in Google Scholar
2. WHO. Cancer. Retrieved from World Health Organization; 2021, October 17. https://www.who.int/news-room/fact-sheets/detail/cancer.Search in Google Scholar
3. Global Cancer Observatory. Global Cancer Statistics 2020: Nigeria. International Agency for Research on Cancer; 2021.Search in Google Scholar
4. Dhingra, N, Kar, A, Sharma, S. Inhibition of aromatase and cell proliferation of breast cancer and human Placenta choriocarcinoma by Prunus persica extracts. Indian J Pharmaceut Sci 2018;80:903–10, https://doi.org/10.4172/pharmaceutical-sciences.1000437.Search in Google Scholar
5. National Cancer Institute. Drugs approved for breast cancer. Retrieved from National Cancer Institute; 2021, September 9. https://www.cancer.gov/about-cancer/treatment/drugs/breast.Search in Google Scholar
6. National Library of Medicine. Tamoxifen. Retrieved from U.S. National Library of Medicine; 2021. https://medlineplus.gov/druginfo/meds/a682414.html.Search in Google Scholar
7. Mishra, S, Ahmad, S, Kumar, N, Sharma, BK. Annona muricata (the cancer killer): a review. Global J Pharmaceut Res 2013;2:1613–8.Search in Google Scholar
8. Agu, KC, Okolie, PN. Proximate composition, phytochemical analysis, and in vitro antioxidant potentials of extracts of Annona Muricata. Food Sci Nutr 2017;5:1029–36, https://doi.org/10.1002/fsn3.498.Search in Google Scholar
9. George, VC, Kumar, DN, Suresh, P, Kumar, RA. Antioxidant, DNA protective efficacy, and HPLC analysis of Annona muricata (soursop) extracts. J Food Sci Technol 2014;52:2328–35, https://doi.org/10.1007/s13197-014-1289-7.Search in Google Scholar
10. Gajalakshmi, S, Vijayalakshmi, S, Rajeswari, DV. Phytochemical and pharmacological properties of Annona muricata: a review. Int J Pharm Pharm Sci 2012;4:3–6.Search in Google Scholar
11. Najmuddin, S, Romli, MF, Hamid, M, Banu-Alitheen, N, Abd-Rahman, NM. Anti-cancer effect of Annona muricata Linn leaves crude extract (AMCE) on breast cancer cell line. BMC Compl Alternative Med 2016;16:1–20. https://doi.org/10.1186/s12906-016-1290-y.Search in Google Scholar
12. Minarni, Made Artika, I, Julistiono, H, Bermawie, N, Riyanti, EI, Hasim, et al.. Anticancer activity test of ethyl acetate extract of endophytic fungi isolated from soursop leaf (Annona muricata L.). Asian Pac J Trop Med 2017;10:566–71, https://doi.org/10.1016/j.apjtm.2017.06.004.Search in Google Scholar
13. Agu, KC, Okolie, NP, Falodun, A, Engel-Lutz, N. In vitro anticancer assessments of Annona muricata fractions and in vitro antioxidant profile of fractions and isolated acetogenin (15-acetyl guanacone). J Cancer Res Pract 2018;5:53–66, https://doi.org/10.1016/j.jcrpr.2017.12.001.Search in Google Scholar
14. Ghosh, D, Lo, J, Morton, D, Valette, D, Xi, J, Griswold, J, et al.. Novel aromatase inhibitors by structure-guided design. J Med Chem 2012;55:8464–76, https://doi.org/10.1021/jm300930n.Search in Google Scholar
15. Tian, W, Chen, C, Lei, X. CASTp 3.0: computed atlas of surface topography of proteins. Nucleic Acids Res 2019;46:W363–7, https://doi.org/10.1093/nar/gky473.Search in Google Scholar
16. Daina, A, Michielin, O, Zoete, V. SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Sci Rep 2017;7:42717, https://doi.org/10.1038/srep42717.Search in Google Scholar
17. Yang, H. Silico prediction of chemical toxicity for drug design using machine learning methods and structural alerts. Front Chem 2018;6:30, https://doi.org/10.3389/fchem.2018.00030.Search in Google Scholar PubMed PubMed Central
18. Filimonov, DA, Lagunin, AA, Gloriozova, TA, Rudik, AV, Druzhilovskii, DS, Pogodin, PV, et al.. Prediction of the biological activity spectra of organic compounds using the PASS online web resource. Chem Heterocycl Compd 2014;50:444–57, https://doi.org/10.1007/s10593-014-1496-1.Search in Google Scholar
19. Meng, XY, Zhang, HX, Mezei, M, Cui, M. Molecular docking: a powerful approach for structure-based drug discovery. Curr Comput Aided Drug Des 2011;7:146–57, https://doi.org/10.2174/157340911795677602.Search in Google Scholar PubMed PubMed Central
20. Dallakyan, S, Olson, AJ. Small-molecule Library screening by docking with PyRx. Methods Mol Biol 2015; 1263:243–50.10.1007/978-1-4939-2269-7_19Search in Google Scholar PubMed
21. Tsaioun, K, Kates, SA. ADMET for medicinal chemists: a practical guide. Singapore: John Wiley & Sons; 2010:145–200 pp.10.1002/9780470915110.ch4Search in Google Scholar
22. Sasikala, RP, Meena, KS. Molecular docking studies and ADMET properties of compounds from Physalis minima L. Leaves, root and fruit. Innovare Journal of Life Science 2016;4:21–5.Search in Google Scholar
23. Onawole, AT, Sulaiman, KO, Adegoke, RO. Kolapo, TU. Identification of potential inhibitors against the Zika virus using consensus scoring. J Mol Graph Model 2017;73:54–61, https://doi.org/10.1016/j.jmgm.2017.01.018.Search in Google Scholar PubMed
24. Sanguinetti, MC, Tristani-Firouzi, M. hERG potassium channels and cardiac arrhythmia. Nature 2006;440:463–9, https://doi.org/10.1038/nature04710.Search in Google Scholar PubMed
25. Falade, VA, Adelusi, TI, Adedotun, IO, Abdul-Hammed, M, Lawal, TA, Agboluaje, SA. In silico investigation of saponins and tannins as potential inhibitors of SARS-CoV-2 main protease (Mpro). Silico Pharmacol 2021;9:1–15, https://doi.org/10.1007/s40203-020-00071-w.Search in Google Scholar PubMed PubMed Central
26. Abdul-Hammed, M, Adedotun, IO, Olajide, M, Irabor, CO, Afolabi, TI, Gbadebo, IO, et al.. Virtual screening, ADMET profiling, PASS prediction, and bioactivity studies of potential inhibitory roles of alkaloids, phytosterols, and flavonoids against COVID-19 main protease (Mpro). Nat Prod Res 2021;1–8. https://doi.org/10.1080/14786419.2021.1935933.Search in Google Scholar PubMed PubMed Central
27. Aucamp, M, Odendaal, R, Liebenberg, W. Hamman, J. Amorphous azithromycin with improved aqueous solubility and intestinal membrane permeability. Drug Dev Ind Pharm 2015;41:1100–8, https://doi.org/10.3109/03639045.2014.931967.Search in Google Scholar PubMed
28. Lipinski, CAL. Profiling Lead- and drug-like compounds: the rule-of-five revolution. Drug Discov Today 2004;1:337–41, https://doi.org/10.1016/j.ddtec.2004.11.007.Search in Google Scholar PubMed
29. Sulaiman, KO, Kolapo, TU, Onawole, AT, Ataul Islam, M, Adegoke, RO, Badmus, SO. Molecular dynamics and combined docking studies for the identification of Zaire Ebola virus inhibitors. J Biomol Struct Dyn 2019;37:3029–40, https://doi.org/10.1080/07391102.2018.1506362.Search in Google Scholar PubMed
30. Burlingham, BT, Widlanski, TS. An intuitive look at the relationship of Ki and IC50: a more general use for the Dixon plot. J Chem Educ 2003;80:214, https://doi.org/10.1021/ed080p214.Search in Google Scholar
31. Nawwar, M, Ayoub, N, Hussein, S, Hashim, A, El-Sharawy, R, Wende, K, et al.. Flavonol triglycoside and investigation of the antioxidant and cell-stimulating activities of Annona muricata Linn. Arch Pharm 2012;35:761–7, https://doi.org/10.1007/s12272-012-0501-4.Search in Google Scholar PubMed
32. Yahaya, G, Faten, A, Fred, W, Hany, A. Phytochemical screening, anti-oxidant activity and in vitro anticancer potential of ethanolic and water leaves extracts of Annona muricata (Graviola). Asian Pac J Trop Med 2014;7:S355–63.10.1016/S1995-7645(14)60258-3Search in Google Scholar PubMed
33. Minari, J, Okeke, U. Chemopreventive effect of Annona muricata on DMBA-induced cell proliferation in the breast tissues of female albino mice. Egypt J Med Hum Genet 2014;15:327–34, https://doi.org/10.1016/j.ejmhg.2014.05.001.Search in Google Scholar
34. Goel, RK, Singh, D, Lagunin, A, Poroikov, V. PASS-assisted exploration of the new therapeutic potential of natural products. Med Chem Res 2011;20:1509–14, https://doi.org/10.1007/s00044-010-9398-y.Search in Google Scholar
© 2022 Walter de Gruyter GmbH, Berlin/Boston
Articles in the same Issue
- Frontmatter
- Reviews
- Anticancer properties of arylchromenes and arylchromans: an overview
- Solid state lithium ion conductors for lithium batteries
- Performance and kinetics of a fluidized bed anaerobic reactor treating distillery effluent
- Use of biochemical markers for diabetes prevention in the new decade
- Antibreast cancer activities of phytochemicals from Anonna muricata using computer-aided drug design (CADD) approach
- Alkaline-earth metal(II) complexes of salinomycin – spectral properties and antibacterial activity
- Use of heterogeneous catalysis in sustainable biofuel production
- Antibacterial, antioxidant and cytotoxic activities of the stem bark of Archidendron jiringa (Jack) I.C. Nielsen
- A review of sludge production in South Africa municipal wastewater treatment plants, analysis of handling cost and potential minimization methods
- Cu-Catalysed tandem reactions for building poly hetero atom heterocycles-green chemistry tool
- Optimizing Cr(VI) adsorption parameters on magnetite (Fe3O4) and manganese doped magnetite (MnxFe(3-x)O4) nanoparticles
- Fabaceae: a significant flavonoid source for plant and human health
- A novel application of synthesised based squarylium dyes on nylon 6, and silk woven fabrics
- Chromatographic characterization of the fusion protein SARS-CoV-2 S protein (RBD)-hFc
- Ethnopharmacology, phytochemistry and a new chemotaxonomic marker in Oldenlandia affinis (Roem. & Schult.) DC. Rubiaceae
- Extraction, isolation and characterization of secondary metabolites in the leaves of Morinda lucida from Oshiegbe in Ebonyi State
- Lead optimisation efforts on a molecular prototype of the immunomodulatory parasitic protein ES-62
- Catalytic applications of graphene oxide towards the synthesis of bioactive scaffolds through the formation of carbon–carbon and carbon–heteroatom bonds
- Synthesis, characterization, DFT and molecular docking studies of acetone O-((2,5-dichlorophenyl)sulfonyl) oxime
- Design of membrane systems
- Conceptual design and cost-efficient environmentally Benign synthesis of beta-lactams
- Synthesis and characterization of alkaloid derived hydrazones and their metal (II) complexes
- The spontaneity of chemical reactions: challenges with handling the concept and its implications
- Copper nanoparticles catalyzed carbon–heteroatom bond formation and synthesis of related heterocycles by greener procedures
- Tellurium in carbohydrate synthesis
- Conformational preferences and intramolecular hydrogen bonding patterns of tetraflavaspidic acid BBBB – a tetrameric acylphloroglucinol
- Phytochemical and antioxidant studies of Hibiscus Cannabinus seed oil
- Polyaniline mediated heterogeneous catalysis in the preparation of heterocyclic derivatives through carbon–heteroatom bond formations
- A comparison of two digestion methods and heavy metals determination in sediments
- Synthesis, properties and catalysis of quantum dots in C–C and C-heteroatom bond formations
- Recyclable magnetically retrievable nanocatalysts for C–heteroatom bond formation reactions
- Small molecules as next generation biofilm inhibitors and anti-infective agents
- Toxicity of tellurium and its compounds
- Biodegradable polycaprolactone (PCL) based polymer and composites
- Quality of poultry meat- the practical issues and knowledge based solutions
Articles in the same Issue
- Frontmatter
- Reviews
- Anticancer properties of arylchromenes and arylchromans: an overview
- Solid state lithium ion conductors for lithium batteries
- Performance and kinetics of a fluidized bed anaerobic reactor treating distillery effluent
- Use of biochemical markers for diabetes prevention in the new decade
- Antibreast cancer activities of phytochemicals from Anonna muricata using computer-aided drug design (CADD) approach
- Alkaline-earth metal(II) complexes of salinomycin – spectral properties and antibacterial activity
- Use of heterogeneous catalysis in sustainable biofuel production
- Antibacterial, antioxidant and cytotoxic activities of the stem bark of Archidendron jiringa (Jack) I.C. Nielsen
- A review of sludge production in South Africa municipal wastewater treatment plants, analysis of handling cost and potential minimization methods
- Cu-Catalysed tandem reactions for building poly hetero atom heterocycles-green chemistry tool
- Optimizing Cr(VI) adsorption parameters on magnetite (Fe3O4) and manganese doped magnetite (MnxFe(3-x)O4) nanoparticles
- Fabaceae: a significant flavonoid source for plant and human health
- A novel application of synthesised based squarylium dyes on nylon 6, and silk woven fabrics
- Chromatographic characterization of the fusion protein SARS-CoV-2 S protein (RBD)-hFc
- Ethnopharmacology, phytochemistry and a new chemotaxonomic marker in Oldenlandia affinis (Roem. & Schult.) DC. Rubiaceae
- Extraction, isolation and characterization of secondary metabolites in the leaves of Morinda lucida from Oshiegbe in Ebonyi State
- Lead optimisation efforts on a molecular prototype of the immunomodulatory parasitic protein ES-62
- Catalytic applications of graphene oxide towards the synthesis of bioactive scaffolds through the formation of carbon–carbon and carbon–heteroatom bonds
- Synthesis, characterization, DFT and molecular docking studies of acetone O-((2,5-dichlorophenyl)sulfonyl) oxime
- Design of membrane systems
- Conceptual design and cost-efficient environmentally Benign synthesis of beta-lactams
- Synthesis and characterization of alkaloid derived hydrazones and their metal (II) complexes
- The spontaneity of chemical reactions: challenges with handling the concept and its implications
- Copper nanoparticles catalyzed carbon–heteroatom bond formation and synthesis of related heterocycles by greener procedures
- Tellurium in carbohydrate synthesis
- Conformational preferences and intramolecular hydrogen bonding patterns of tetraflavaspidic acid BBBB – a tetrameric acylphloroglucinol
- Phytochemical and antioxidant studies of Hibiscus Cannabinus seed oil
- Polyaniline mediated heterogeneous catalysis in the preparation of heterocyclic derivatives through carbon–heteroatom bond formations
- A comparison of two digestion methods and heavy metals determination in sediments
- Synthesis, properties and catalysis of quantum dots in C–C and C-heteroatom bond formations
- Recyclable magnetically retrievable nanocatalysts for C–heteroatom bond formation reactions
- Small molecules as next generation biofilm inhibitors and anti-infective agents
- Toxicity of tellurium and its compounds
- Biodegradable polycaprolactone (PCL) based polymer and composites
- Quality of poultry meat- the practical issues and knowledge based solutions
