New Phosphoramides Containing 2-Amino-1,4-Naphthaquinone Moiety As Anticancer and Antibacterial Agents: Experimental and Theoretical Evaluations

New Phosphoramides Containing 2-Amino-1,4-Naphthaquinone Moiety As Anticancer and Antibacterial Agents: Experimental and Theoretical Evaluations Publisher

Gholivand K¹ ; Faraghi M¹ ; Fallah N² ; Vahabirad M³ ; Malekshah RE⁴ ; Salimi F⁵ ; Pournasirroudbaneh M⁶

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1. Department of Chemistry, Faculty of Sciences, Tarbiat Modares University, Tehran, Iran
2. Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran
3. Department of Clinical Biochemistry, School of Medicine, Hamadan University of Medical Sciences, Hamadan, Iran
4. Medical Biomaterial Research Centre (MBRC), Tehran University of Medical Sciences, Tehran, Iran
5. Department of Virology, Faculty of Medical Sciences, Tarbiat Modares University, Tehran, Iran
6. Department of Periodontics, School of Dentistry, Tehran University of Medical Sciences, Tehran, Iran

Source: Process Biochemistry Published:2023

Abstract

In this study, two novel phosphoramides containing 2-Amino-1,4-naphthaquinone, O,O-diethyl (2-naphthaleneyl-1,4-dione)phosphoramidothioate (NPT) and N,N´- bis(2-naphthaleneyl-1,4-dione) phenylphosphonic diamide (NPA) as cytotoxic agents, were synthesized and characterized by using spectroscopic methods. The anticancer activities of the synthesized compounds were investigated against the human breast cancer cell line SK-BR-3 and normal cells PC12 using MTT assay. The resulting data showed that NPA with an IC50 value of 6.384 μg/ml had a better inhibitory effect against cancer cells than NPT (IC50 = 10.08 μg/ml). According to the annexin V‐FITC/PI results, after treating cancer cells with synthesized compounds for 24 h, the overall population of apoptotic cells increased from 14.96% in the control group to 97.45%, 75.58% in NPA and NPT-treated cells, respectively. Given these results, NPA and NPT have considerable toxicity and apoptosis-inducing ability against SK-BR-3. The cytotoxicity results were supported by a molecular docking study to compute the interactions between synthesized compounds and transcription factor DNA (PDB ID: 1bg1). In order to know the structure-activity relationship (SAR) of synthesized compounds, the values of the quantum-mechanical descriptors were investigated computationally by the DFT method, and the obtained results were then compared with Cyclophosphamide (CY) as a standard anticancer drug. These results were in good accordance with those of in vitro investigation and molecular docking study. Antibacterial study of phosphoramides against Gram-negative (Escherichia coli) and Gram-positive bacteria (Staphylococcus aureus) was carried out MIC, MBC and DDA methods. Additionally, the molecular docking study was performed for the interaction between E. coli beta-lactamase (PDB: 4HBT) and S. aureus beta-lactamase (PDB: 1MWU) with target compounds, the obtained results showed that these compounds are appropriate ligands for antibacterial activity against Staphylococcus aureus and Escherichia coli bacteria. © 2023

2. Experimental and Theoretical Evaluation of Biological Properties of a Phosphoramide Functionalized Graphene Oxide, Biocatalysis and Agricultural Biotechnology (2023)

3. Design, Synthesis, Characterization, Enzymatic Inhibition Evaluations, and Docking Study of Novel Quinazolinone Derivatives, International Journal of Biological Macromolecules (2021)

Experts (# of related papers)

Bagher Larijani (1)

Mohammad Mahdavi (1)

Style	Citing Format
MLA	Gholivand K, et al.. "New Phosphoramides Containing 2-Amino-1,4-Naphthaquinone Moiety As Anticancer and Antibacterial Agents: Experimental and Theoretical Evaluations." Process Biochemistry, vol. 132, no. , 2023, pp. 97-109.
APA	Gholivand K, Faraghi M, Fallah N, Vahabirad M, Malekshah RE, Salimi F, Pournasirroudbaneh M (2023). New Phosphoramides Containing 2-Amino-1,4-Naphthaquinone Moiety As Anticancer and Antibacterial Agents: Experimental and Theoretical Evaluations. Process Biochemistry, 132(), 97-109.
Chicago	Gholivand K, Faraghi M, Fallah N, Vahabirad M, Malekshah RE, Salimi F, Pournasirroudbaneh M. "New Phosphoramides Containing 2-Amino-1,4-Naphthaquinone Moiety As Anticancer and Antibacterial Agents: Experimental and Theoretical Evaluations." Process Biochemistry 132, no. (2023): 97-109.
Harvard	Gholivand K et al. (2023) 'New Phosphoramides Containing 2-Amino-1,4-Naphthaquinone Moiety As Anticancer and Antibacterial Agents: Experimental and Theoretical Evaluations', Process Biochemistry, 132(), pp. 97-109.
Vancouver	Gholivand K, Faraghi M, Fallah N, Vahabirad M, Malekshah RE, Salimi F, et al.. New Phosphoramides Containing 2-Amino-1,4-Naphthaquinone Moiety As Anticancer and Antibacterial Agents: Experimental and Theoretical Evaluations. Process Biochemistry. 2023;132():97-109.
BibTex	@article{ author = {Gholivand K and Faraghi M and Fallah N and Vahabirad M and Malekshah RE and Salimi F and Pournasirroudbaneh M}, title = {New Phosphoramides Containing 2-Amino-1,4-Naphthaquinone Moiety As Anticancer and Antibacterial Agents: Experimental and Theoretical Evaluations}, journal = {Process Biochemistry}, volume = {132}, number = {}, pages = {97-109}, year = {2023} }
RIS	TY - JOUR AU - Gholivand K AU - Faraghi M AU - Fallah N AU - Vahabirad M AU - Malekshah RE AU - Salimi F AU - Pournasirroudbaneh M TI - New Phosphoramides Containing 2-Amino-1,4-Naphthaquinone Moiety As Anticancer and Antibacterial Agents: Experimental and Theoretical Evaluations JO - Process Biochemistry VL - 132 IS - SP - 97 EP - 109 PY - 2023 ER -

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