Synthesis, Molecular Mechanism and Pharmacokinetic Studies of New Epoxy Lignan‐Based Derivatives

Rifai, Yusnita; Tani, Harold B.; Amir, Muhammad Nur; Aswad, Muhammad; Lallo, Subehan; Wahyudin, Elly

doi:10.1002/ardp.201600069

Cited by 5 publications

(2 citation statements)

References 24 publications

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“…Meanwhile the synthetic epoxylignan of DMEO related compound was reported to inhibit the mRNA expression of protein patched homolog (Ptch) in human pancreatic cancer cells (PANC1) and thus is considered to be a prospective drug candidate to treat cancer related to the GLI signaling pathway. However, poor solubility remains the main limitation of DMEO 7 , hence making drug administration in vivo difficult. The nanoencapsulation of DMEO is one of the ways of overcoming the problem.…”

Section: Introductionmentioning

confidence: 99%

Characterization and stability evaluation of nanoencapsulated epoxylignans

et al. 2018

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3',6-dimethoxy-3'',4''-(methylenedioxy)-2,5-epoxylignan-4'-ol (DMEO), an epoxylignan isolated from , has currently captured attention for its Piper nigrum potential antitumor effect. However, low stability is limiting its therapeutic application. The application of nanocapsulation would be the main strategy for overcoming this problem. DMEO-loaded nanocapsules were prepared by an emulsion-diffusion method using Eudragit RL 100 (at concentrations of 1, 1.5 and 2%) and polyvinyl alcohol. As the polymer content increased, the encapsulation efficiency and mean particle size also increased. After 6 months of storage at 25°C (0% RH), no crystalline peaks were observed in the diffraction patterns of all nanocapsules, thereby suggested that the physical stability of nanoencapsulated DMEO was not affected by the concentration ratio of the polymer−stabilizer combinations.

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Section: Introductionmentioning

confidence: 99%

Characterization and stability evaluation of nanoencapsulated epoxylignans

et al. 2018

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“…Increasingly exponential computing capabilities are an opportunity to develop simulations and calculations in drug design. The computer offers a method known as in silico which is a complement of the in vitro and in vivo methods commonly used in the drug discovery process [2][3][4].…”

Section: Introductionmentioning

confidence: 99%

Search for Glioma Direct Binding Site of Alkaloid Using Protein-Ligand Ant System®

Rifai

2018

Asian J Pharm Clin Res

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Objective: This research aims to know the best affinity and the best chemical conformation of anticancer compounds from alkaloid groups that have closed direction to Glioma-associated oncogene using protein-ligand ant system (PLANTS®). The interaction energy and hydrogen bond are included as evaluated targets.Methods: In this research, 27 ligands with root mean square deviation score at 1.614 Å and cyclopamine as native ligand are used. Meanwhile, staurosporinone acts as gliomas directed-binding-site-internal-control. Each ligand is docked in GLI with Protein Data Bank code 2GLI using two methods, GLI contains water and without water.Results: PLANTS® score for native ligand in the first and the second method is −73.9002 and −73.2700, respectively. Pancracristine, homoharringtonine, and sanguinarine showed PLANTS® score closed to the cyclopamine score result, but their hydrogen bond interaction differed from native ligan interaction. Evodiamine ligand has a good score and hydrogen bond to the same amino acid of protein GLI, which are GLU 175 and THR 173. This result indicated that evodiamine has the same identical mechanism as staurosporinone.Conclusion: The evodiamine is determined to have the same working mechanism as a GLI inhibitor.

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Characterization and Biological Evaluation of Solid Dispersed Nanoparticles of Synthetic Epoksilignan Targeting Pancreatic Cancer Cell as an Anticancer Agent

Rifai

Nurhaidah

Tanggulungan

et al. 2021

j biomed nanotechnol

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MMEO (3′-methoxy-3′,4″(methylenedioxy)-2,5-epoksilignan-4′ol-6-on) is a derivative of DMEO (3′-methoxy-3″,4″(methylenedioxy)-2,5-epoksilignan-4′,6-diol) synthesized through demethylation using dimethylsulfoxide-acetic anhydride reagent. MMEO inhibits Hedgehog signaling at a concentration of 4.1 μM. The current study aimed to formulate MMEO as solid dispersed nanoparticles and determine their physicochemical properties and inhibitory activities. XRD (X-ray diffraction) analysis showed that the crystalline particles of the pure compound MMEO was smaller than MMEO nanoparticles. Image J software showed that at concentrations of 25 mg/mL and 50 mg/mL, the average nanoparticle sizes were 852.26 nm and 178.65 nm, respectively. Therefore, the MMEO solid dispersion system with the PEG 4000 polymer increases the solubility of MMEO. The higher the concentration of PEG 4000 the greater the solubility of MMEO. Treating pancreatic cancer cell lines with MMEO silenced the smoothened function by downregulating mRNA Ptch expression. This study suggests that MMEO may inhibit pancreatic cancer disease.

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Synthesis, Molecular Mechanism and Pharmacokinetic Studies of New Epoxy Lignan‐Based Derivatives

Cited by 5 publications

References 24 publications

Characterization and stability evaluation of nanoencapsulated epoxylignans

Characterization and stability evaluation of nanoencapsulated epoxylignans

Search for Glioma Direct Binding Site of Alkaloid Using Protein-Ligand Ant System®

Characterization and Biological Evaluation of Solid Dispersed Nanoparticles of Synthetic Epoksilignan Targeting Pancreatic Cancer Cell as an Anticancer Agent

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