skip to main content

Potential of C-Phenylcalix[4]Resorcinarene Epoxide Compound as Drug Delivery Agent in Breast Cancer Cells MCF-7

Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta, Indonesia

Received: 22 Oct 2021; Revised: 20 Feb 2022; Accepted: 24 Feb 2022; Published: 31 Mar 2022.
Open Access Copyright 2022 Jurnal Kimia Sains dan Aplikasi under

Citation Format:
Cover Image

Cancer therapy through conventional chemotherapy has been widely applied; however, one of the main disadvantages of chemotherapy is the non-selective targeting of cancer cells which causes various adverse side effects. The development of drug delivery agents that are more selective and effective in cancer therapy needs to be performed so that the drugs have a therapeutic effect and minimize side effects. In this study, the compound C-phenylcalyx[4]resorcinarene epoxide (CFKRE) has acted as a drug delivery agent because it can form host complex interactions with ligands. The CFKRE compound was synthesized through two reaction steps: the condensation and alkylation reactions of the epoxide. The structure was analyzed using FTIR, 1H-, and 13C-NMR spectrophotometers and then tested for in vitro cytotoxicity using the MTT assay. The results showed that 70% yield of CFKRE was obtained. Molecular docking analysis of CFKRE compounds against PDGFR and EGFR proteins showed high binding energy compared to conventional chemotherapeutic agents. Molecular dynamic studies showed that CFKRE compounds could form a host-ligand complex with a −350.4 kcal/mol binding energy. Cytotoxic assay of CFKRE compound against MCF-7 breast cancer cells and Vero cells gave IC50 values of 4.04 and 29.59 μg/mL, respectively. These results indicated that CFKRE compounds are not toxic and have the potential to be utilized as new candidates for drug delivery agents.

Fulltext View|Download
Keywords: C-phenylcalyx[4]resorcinarene epoxide; drug delivery; breast cancer
Funding: Universitas Gadjah Mada

Article Metrics:

  1. Christine L. Chaffer, Robert A. Weinberg, A perspective on cancer cell metastasis, Science, 331, 6024, (2011), 1559-1564
  2. Rebecca S. Y. Wong, Apoptosis in cancer: from pathogenesis to treatment, Journal of Experimental & Clinical Cancer Research, 30, 1, (2011), 1-14
  3. Bruce A. Chabner, Thomas G. Roberts, Chemotherapy and the war on cancer, Nature Reviews Cancer, 5, 1, (2005), 65-72
  4. Sudipta Senapati, Arun Kumar Mahanta, Sunil Kumar, Pralay Maiti, Controlled drug delivery vehicles for cancer treatment and their performance, Signal Transduction and Targeted Therapy, 3, 1, (2018), 1-19
  5. Jessica J. Tao, Kala Visvanathan, Antonio C. Wolff, Long term side effects of adjuvant chemotherapy in patients with early breast cancer, The Breast, 24, (2015), S149-S153
  6. Karol Bukowski, Mateusz Kciuk, Renata Kontek, Mechanisms of multidrug resistance in cancer chemotherapy, International Journal of Molecular Sciences, 21, 9, (2020), 3233
  7. Oktay Tacar, Pornsak Sriamornsak, Crispin R. Dass, Doxorubicin: an update on anticancer molecular action, toxicity and novel drug delivery systems, Journal of Pharmacy and Pharmacology, 65, 2, (2013), 157-170
  8. Dengguo Wei, Xiaolu Jiang, Lu Zhou, Jing Chen, Zheng Chen, Chong He, Kun Yang, Ying Liu, Jianfeng Pei, Luhua Lai, Discovery of multitarget inhibitors by combining molecular docking with common pharmacophore matching, Journal of Medicinal Chemistry, 51, 24, (2008), 7882-7888
  9. Emmy Yuanita, Pranowo Harno Dwi, Mustofa Mustofa, Swasono Respati Tri, Jufriza Syahri, Jumina Jumina, Synthesis, characterization and molecular docking of chloro-substituted hydroxyxanthone derivatives, Chemistry Journal of Moldova, 14, 1, (2019), 68-76
  10. Jose Baselga, Why the epidermal growth factor receptor? The rationale for cancer therapy, The Oncologist, 7, S4, (2002), 2-8
  11. Mengrui Liu, Hongliang Du, Wenjia Zhang, Guangxi Zhai, Internal stimuli-responsive nanocarriers for drug delivery: Design strategies and applications, Materials Science and Engineering: C, 71, (2017), 1267-1280
  12. Zhe Wang, Xiangping Deng, Jinsong Ding, Wenhu Zhou, Xing Zheng, Guotao Tang, Mechanisms of drug release in pH-sensitive micelles for tumour targeted drug delivery system: A review, International Journal of Pharmaceutics, 535, 1-2, (2018), 253-260
  13. Sandeep J. Sonawane, Rahul S. Kalhapure, Thirumala Govender, Hydrazone linkages in pH responsive drug delivery systems, European Journal of Pharmaceutical Sciences, 99, (2017), 45-65
  14. Yue Zhou, Hui Li, Ying-Wei Yang, Controlled drug delivery systems based on calixarenes, Chinese Chemical Letters, 26, 7, (2015), 825-828
  15. Anis Abdul Karim, Qingqing Dou, Zibiao Li, Xian Jun Loh, Emerging supramolecular therapeutic carriers based on host–guest interactions, Chemistry–An Asian Journal, 11, 9, (2016), 1300-1321
  16. Fazel Nasuhi Pur, Karim Akbari Dilmaghani, Calixplatin: novel potential anticancer agent based on the platinum complex with functionalized calixarene, Journal of Coordination Chemistry, 67, 3, (2014), 440-448
  17. Jingxin Mo, Paul K. Eggers, Zhi-Xiang Yuan, Colin L. Raston, Lee Yong Lim, Paclitaxel-loaded phosphonated calixarene nanovesicles as a modular drug delivery platform, Scientific Reports, 6, 1, (2016), 1-12
  18. M. D. Shah, Y. K. Agrawal, Calixarene: A new architecture in the analytical and pharmaceutical technology, Journal of Scientific and Industrial Research (JSIR), 71, (2012), 21-26
  19. Ângelo de Fátima, Sergio A. Fernandes, Adão Aparecido Sabino, Calixarenes as new platforms for drug design, Current Drug Discovery Technologies, 6, 2, (2009), 151-170
  20. Ali Yousaf, Shafida Abd Hamid, Noraslinda M. Bunnori, A. A. Ishola, Applications of calixarenes in cancer chemotherapy: facts and perspectives, Drug Design, Development and Therapy, 9, (2015), 2831
  21. Rodrigo Galindo-Murillo, María Eugenia Sandoval-Salinas, Joaquín Barroso-Flores, In silico design of monomolecular drug carriers for the tyrosine kinase inhibitor drug imatinib based on calix-and thiacalix [n] arene host molecules: a DFT and molecular dynamics study, Journal of Chemical Theory and Computation, 10, 2, (2014), 825-834

Last update:

  1. Oliveramine: An Isolated Alkaloid from Fagraea fragrans (Tembesu) Bark

    Dasril Basir, Jefri Liasta, Annisa Amelia, Miksusanti Miksusanti, Susilawati Susilawati. Jurnal Kimia Sains dan Aplikasi, 25 (7), 2022. doi: 10.14710/jksa.25.7.264-269

Last update: 2023-11-29 06:24:39

No citation recorded.