Anti-breast Adenocarcinoma and Anti-urease Anti-tyrosinase Properties of 5-Pentylresorcinol as Natural Compound with Molecular Docking Studies.

5-Pentylresorcinol is a type of the group of resorcinol compounds that is resorcinol in that has hydrogen atom at position 5 is replaced by a pentyl group. It has a role as a lichen metabolite. This compound showed excellent to good inhibitory activities against studied these enzymes with IC50 values of 65.96 µM for urease and 34.81 µM for tyrosinase. Standard compounds for enzymes had IC50 values of 1.94±0.24 µM against urease and 84.36±5.17 µM against tyrosinase. The IC50 of 5-pentylresorcinol against MCF7 cell line was 165.72 µg/mL; against Hs 578Bst cell line was 102.14 µg/mL; against Hs 319.T cell line was 12.34 µg/mL; and against UACC-3133 cell line was 73.07 µg/mL, respectively. The chemical activities of 5-pentylresorcinol against urease and tyrosinase were evaluated using the molecular modeling study. The anti-cancer activity of 5-pentylresorcinol was also investigated by treating the compound on the BRCT repeat region from the breast cancer-associated protein (BRCA1), and their interactions were assessed utilizing the molecular docking calculations. The results revealed the probable interactions and their characteristics at an atomic level. The docking scores of 5-pentylresorcinol against urease, tyrosinase, and BRCA1 are -3.073, -5.262, and -3.238 (kcal/mol), respectively.

[1]  A. Pardakhty,et al.  3D‐QSAR, molecular docking, molecular dynamics, and ADME/T analysis of marketed and newly designed flavonoids as inhibitors of Bcl‐2 family proteins for targeting U‐87 glioblastoma , 2021, Journal of cellular biochemistry.

[2]  A. Amine,et al.  The Kinetic and Analytical Aspects of Enzyme Competitive Inhibition: Sensing of Tyrosinase Inhibitors , 2021, Biosensors.

[3]  M. Mehrbani,et al.  Naringenin attenuates cell viability and migration of C6 glioblastoma cell line: a possible role of hedgehog signaling pathway , 2021, Molecular Biology Reports.

[4]  Fang Wang,et al.  Recent advances in the design and discovery of synthetic tyrosinase inhibitors. , 2021, European journal of medicinal chemistry.

[5]  K. Dimas,et al.  Tumor Chemosensitivity Assays Are Helpful for Personalized Cytotoxic Treatments in Cancer Patients , 2021, Medicina.

[6]  U. Farooq,et al.  Design and synthesis of thiobarbituric acid analogues as potent urease inhibitors , 2021 .

[7]  A. Prabhu,et al.  Unravelling the human triple negative breast cancer suppressive activity of biocompatible zinc oxide nanostructures influenced by Vateria indica (L.) fruit phytochemicals. , 2021, Materials science & engineering. C, Materials for biological applications.

[8]  Liuping Fan,et al.  Understanding the combined effect and inhibition mechanism of 4-hydroxycinnamic acid and ferulic acid as tyrosinase inhibitors. , 2021, Food chemistry.

[9]  A. Pardakhty,et al.  Evaluation of potential anti-RNA-dependent RNA polymerase (RdRP) drugs against the newly emerged model of COVID-19 RdRP using computational methods , 2021, Biophysical Chemistry.

[10]  Emad Mahrous Awwad,et al.  Mn3O4 nanoparticles: Synthesis, characterization and their antimicrobial and anticancer activity against A549 and MCF-7 cell lines , 2020, Saudi journal of biological sciences.

[11]  A. Siczek,et al.  Effectiveness of the use of urease inhibitors in agriculture: a review , 2021, International Agrophysics.

[12]  R. Carlini,et al.  A Catalytic, Oxidative Synthesis of Olivetol, Methyl Olivetolate and Orthogonally Protected Methyl Ether Derivatives , 2021 .

[13]  Jeffrey J. Gray,et al.  Advances to tackle backbone flexibility in protein docking. , 2020, Current opinion in structural biology.

[14]  Dan Yang,et al.  Characterization of antioxidant, α-glucosidase and tyrosinase inhibitors from the rhizomes of Potentilla anserina L. and their structure-activity relationship. , 2020, Food chemistry.

[15]  T. Vanek,et al.  Synthesis, inhibitory activity and in silico docking of dual COX/5-LOX inhibitors with quinone and resorcinol core. , 2020, European journal of medicinal chemistry.

[16]  Le Zhang,et al.  Progress in molecular docking , 2019, Quantitative Biology.

[17]  A. Bishayee,et al.  Targeting autophagy using natural compounds for cancer prevention and therapy , 2019, Cancer.

[18]  Rengül Çetin-Atalay,et al.  Synthesis, anticancer activity, toxicity evaluation and molecular docking studies of novel phenylaminopyrimidine - (thio)urea hybrids as potential kinase inhibitors , 2019, Comput. Biol. Chem..

[19]  J. Trujillo-Ferrara,et al.  Selection of a GPER1 Ligand via Ligand-based Virtual Screening Coupled to Molecular Dynamics Simulations and Its Anti-proliferative Effects on Breast Cancer Cells. , 2019, Anti-Cancer Agents in Medicinal Chemistry.

[20]  Yu-hua Fan,et al.  Three Co(II) complexes with a sexidentate N2O4-donor bis-Schiff base ligand: Synthesis, crystal structures, DFT studies, urease inhibition and molecular docking studies , 2017 .

[21]  Łukasz Berlicki,et al.  Novel organophosphorus scaffolds of urease inhibitors obtained by substitution of Morita-Baylis-Hillman adducts with phosphorus nucleophiles. , 2017, European journal of medicinal chemistry.

[22]  M. Rafiq,et al.  Synthesis, kinetic mechanism and docking studies of vanillin derivatives as inhibitors of mushroom tyrosinase. , 2015, Bioorganic & medicinal chemistry.

[23]  Łukasz Berlicki,et al.  Bis(aminomethyl)phosphinic Acid, a Highly Promising Scaffold for the Development of Bacterial Urease Inhibitors. , 2015, ACS medicinal chemistry letters.

[24]  Minhui Li,et al.  Two Novel Tyrosinase Inhibitory Sesquiterpenes Induced by CuCl2 from a Marine-Derived Fungus Pestalotiopsis sp. Z233 , 2013, Marine drugs.

[25]  M. Mihăşan.  What in silico molecular docking can do for the ‘bench-working biologists’ , 2012, Journal of Biosciences.

[26]  Yuguang C. Li,et al.  Synthesis, structures and urease inhibition studies of copper(II) and nickel(II) complexes with bidentate N,O-donor Schiff base ligands. , 2012, Journal of inorganic biochemistry.

[27]  M. Mezei,et al.  Molecular docking: a powerful approach for structure-based drug discovery. , 2011, Current computer-aided drug design.

[28]  Shivendra V. Singh,et al.  Ginsenoside Rh2-mediated G1 Phase Cell Cycle Arrest in Human Breast Cancer Cells Is Caused by p15Ink4B and p27Kip1-dependent Inhibition of Cyclin-dependent Kinases , 2009, Pharmaceutical Research.

[29]  T. Bisogno,et al.  Design, synthesis, binding, and molecular modeling studies of new potent ligands of cannabinoid receptors. , 2007, Bioorganic & medicinal chemistry.

[30]  J. Kang,et al.  A New α-Pyrone Derivative, 6-((E)-Hept-1-enyl)-α-pyrone, with Tyrosinase Inhibitory Activity from a Marine Isolate of the Fungus Botrytis , 2007 .