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Adv Pharm Bull. 2022;12(3): 603-612.
doi: 10.34172/apb.2022.063
PMID: 35935043
PMCID: PMC9348534
Scopus ID: 85140275448
  Abstract View: 517
  PDF Download: 169

Research Article

Preparation and Cytotoxic Evaluation of PGV-1 Derivative, CCA-1.1, as a New Curcumin Analog with Improved-Physicochemical and Pharmacological Properties

Rohmad Yudi Utomo 1,2 ORCID logo, Febri Wulandari 1 ORCID logo, Dhania Novitasari 1 ORCID logo, Beni Lestari 1 ORCID logo, Ratna Asmah Susidarti 1,2 ORCID logo, Riris Istighfari Jenie 1,3 ORCID logo, Jun-ya Kato 4, Sardjiman Sardjiman 2 ORCID logo, Edy Meiyanto 1,3* ORCID logo

1 Cancer Chemoprevention Research Center, Faculty of Pharmacy, Universitas Gadjah Mada (UGM), Sekip Utara, Yogyakarta 55281, Indonesia.
2 Medicinal Chemistry Laboratory, Department of Pharmaceutical Chemistry, Faculty of Pharmacy, UGM, Sekip Utara, Yogyakarta 55281, Indonesia.
3 Macromolecular Engineering Laboratory, Department of Pharmaceutical Chemistry, Faculty of Pharmacy UGM, Sekip Utara, Yogyakarta 55281, Indonesia.
4 Laboratory of Tumor Cell Biology, Division of Bioligical Science, Graduate School of Science and Technology, Nara Institute of Science and Technology, Nara, 630-0192, Japan.
*Corresponding Author: Edy Meiyanto, Phone: +62 812 2735 092, Fax: +62274 543120, Email: edy_meiyanto@ugm.ac.id, Email: edy_meiyanto@ugm.ac.id

Abstract

Purpose: This study aimed to challenge the anticancer potency of pentagamavunone-1 (PGV-1) and obtain a new compound (Chemoprevention-Curcumin Analog 1.1, CCA-1.1) withimproved chemical and pharmacological properties.Methods: CCA-1.1 was prepared by changing the ketone group of PGV-1 into a hydroxylgroup with NaBH4 as the reducing agent. The product was purified under preparative layerchromatography and confirmed with HPLC to show about 93% purity. It was tested for itssolubility, stability, and cytotoxic activities on several cancer cells. The structure of the productwas characterized using 1HNMR, 13C-NMR, FT-IR, and HR-mass spectroscopy.Results: Molecular docking analysis showed that CCA-1.1 performed similar or better interactionto NF-κB pathway-related signaling proteins (HER2, EGFR, IKK, ER-alpha, and ER-beta) andreactive oxygen species (ROS) metabolic enzymes (NQO1, NQO2, GSTP1, AKC1R1, andGLO1) compared with PGV-1, indicating that CCA-1.1 exhibits the same or better anticanceractivity than PGV-1. CCA-1.1 also showed better solubility and stability than PGV-1 in aqueoussolution at pH 1.0–7.4 under light exposure at room temperature. The cytotoxic activities ofCCA-1.1 against several (10) cancer cell lines revealed the same or better potency than PGV-1.Conclusion: In conclusion, CCA-1.1 performs better chemical and anticancer properties thanPGV-1 and shows promise as an anticancer agent with high selectivity.
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Submitted: 04 May 2020
Revision: 05 Jan 2021
Accepted: 02 Jul 2021
ePublished: 04 Jul 2021
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