Publications by authors named "Ateyatallah Aljuhani"

6 Publications

  • Page 1 of 1

Design of molecular hybrids of phthalimide-triazole agents with potent selective MCF-7/HepG2 cytotoxicity: Synthesis, EGFR inhibitory effect, and metabolic stability.

Bioorg Chem 2021 Jun 22;111:104835. Epub 2021 Mar 22.

Pharmacognosy and Pharmaceutical Chemistry Department, College of Pharmacy, Taibah University, Al-Madinah Al-Munawarah, Saudi Arabia; Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Al-Azhar University, 11884 Nasr City, Cairo, Egypt.

This study reports an efficient and convenient click chemistry synthesis of a novel series of phthalimide scaffold linked to 1,2,3 triazole ring and terminal lipophilic fragments. Structures of newly synthesized compounds were well characterized by different spectroscopic tools. In vitro MTT cytotoxicity assay was performed comparing the cytotoxic effects of newly synthesized compounds to staurosporine using three different types: human liver cancer cell line (HepG2), Michigan cancer foundation-7 (MCF-7) and human colorectal carcinoma cell line (HCT116). The initial screening showed excellent to moderate anticancer activity for these newly synthesized compounds with high degree of cell line selectivity with micromolar (µM) half maximal inhibitory concentration (IC) values against tumor cells. The SAR analysis of these derivatives confirmed the role of molecular fragments including phthalimide, linker, triazole, and terminal tails in correlation to activity. In addition, enzymatic inhibitory assay against wild type EGFR was performed for the most active compounds to get more details about their mechanism of action. In order to further explore their binding affinities, molecular docking simulation was studied against EGFR site. The results obtained from molecular docking study and those obtained from cytotoxic screening were correlated. One of the most prominent analogs is (6f) with terminal disubstituted ring and amide linker showed selective MCF-7 cytotoxicity profile with IC 0.22 µM and 79 nM to EGFR target. Extensive structure activity relationship (SAR) analyses were also carried out. The pharmacokinetic profile of (6f) was studied showing good metabolic stability and long duration behavior. This design offered a potent selective anticancer phthalimide-triazole leads for further optimization in cancer drug discovery.
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http://dx.doi.org/10.1016/j.bioorg.2021.104835DOI Listing
June 2021

Novel Hexadeca-Substituted Metal Free and Zinc(II) Phthalocyanines; Design, Synthesis and Photophysicochemical Properties.

Molecules 2018 Dec 26;24(1). Epub 2018 Dec 26.

Department of Chemistry, Taibah University, Al-Madinah Al Munawrah, P.O. Box 344, Saudi Arabia.

The syntheses of a novel 1,4,8,11,15,18,22,25-octahexyloxy-2,3,9,10,16,17,23,24-octa-(4-trifluoromethoxyphenyl) phthalocyanine () and its zinc(II) phthalocyanine derivative () have been described and characterized by elemental analysis,¹H NMR, C NMR, F NMR, mass, UV-Vis and FT-IR. The newly prepared metal-free phthalocyanine and its zinc(II) counterpart are soluble in most organic solvents. The photophysical and photochemical properties such as aggregation, fluorescence, singlet oxygen generation and photodegradation under light irradiation of these phthalocyanines have been investigated in DMF. The hexadeca-substituted phthalocyanines ( and ) showed longer absorption and emission wavelength values when compared to that of reported phthalocyanine derivatives due to substitution of the all possible positions in the phthalocyanine framework. The zinc(II) phthalocyanine derivative does not only have a good singlet oxygen generation but also has other photophysicochemical properties that enables this phthalocyanine to be useful as a photosensitizer for cancer treatment using photodynamic therapy.
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http://dx.doi.org/10.3390/molecules24010077DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6337579PMC
December 2018

Chitosan-MgO Nanocomposite: One Pot Preparation and Its Utility as an Ecofriendly Biocatalyst in the Synthesis of Thiazoles and [1,3,4]thiadiazoles.

Nanomaterials (Basel) 2018 Nov 8;8(11). Epub 2018 Nov 8.

Department of Chemistry, Faculty of Science, Taibah University, Al-Madinah Al-Mounawrah 30002, Saudi Arabia.

A chitosan-MgO hybrid nanocomposite was prepared using a simple chemical precipitation method and characterized using Fourier transform spectroscopy (FTIR), elemental analysis (EDX), and scanning electron microscopy (SEM). The nanocomposite was served as a powerful ecofriendly basic catalyst under microwave irradiation in the synthesis of two novel series of 5-arylazo-2-hydrazonothiazoles ⁻ and 2-hydrazono[1,3,4]thiadiazoles ⁻, incorporating a sulfonamide group. The structures of the synthesized products were elucidated by spectral data and elemental analyses. Also, their yield percentages were calculated using triethylamine (as a traditional catalyst) and chitosan-MgO nanocomposite (as a green recyclable catalyst) in a comparative study.
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http://dx.doi.org/10.3390/nano8110928DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6266359PMC
November 2018

Molybdenum Trioxide: Efficient Nanosorbent for Removal of Methylene Blue Dye from Aqueous Solutions.

Molecules 2018 Sep 8;23(9). Epub 2018 Sep 8.

Chemistry Department, College of Science, Taibah University, Al-Madinah 30002, Saudi Arabia.

Nano Molybdenum trioxide (α-MoO₃) was synthesized in an easy and efficient approach. The removal of methylene blue (MB) in aqueous solutions was studied using this material. The effects of various experimental parameters, for example contact time, pH, temperature and initial MB concentration on removal capacity were explored. The removal of MB was significantly affected by pH and temperature and higher values resulted in increase of removal capacity of MB. The removal efficiency of Methylene blue was 100% at pH = 11 for initial dye concentrations lower than 150 ppm, with a maximum removal capacity of 152 mg/g of MB as gathered from Langmuir model. By comparing the kinetic models (pseudo first-order, pseudo second-order and intraparticle diffusion model) at various conditions, it has been found that the pseudo second-order kinetic model correlates with the experimental data well. The thermodynamic study indicated that the removal was endothermic, spontaneous and favorable. The thermal regeneration studies indicated that the removal efficiency (99%) was maintained after four cycles of use. Fourier Transform Infrared (FTIR) and Scanning Electron Microscopy (SEM) confirmed the presence of the MB dye on the α-MoO₃ nanoparticles after adsorption and regeneration. The α-MoO₃ nanosorbent showed excellent removal efficiency before and after regeneration, suggesting that it can be used as a promising adsorbent for removing Methylene blue dye from wastewater.
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http://dx.doi.org/10.3390/molecules23092295DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6225373PMC
September 2018

Microwave-Assisted Synthesis of Some Potential Bioactive Imidazolium-Based Room-Temperature Ionic Liquids.

Molecules 2018 Jul 15;23(7). Epub 2018 Jul 15.

Department of Chemistry, Taibah University, Al-Madina Al-Mounawara 30002, Saudi Arabia.

An environmentally-friendly and easy synthesis of a series of novel functionalized imidazolium-based ionic liquids (ILs) is described under both the conventional procedure and microwave irradiation. The structures of newly synthesized room-temperature ionic liquids (RTILs) were established by different spectral analyses. All ILs (⁻) were screened for their in vitro antimicrobial activity against a panel of clinically isolated bacteria. The results of the minimum inhibitory concentration (MIC) and the minimum bactericidal concentration (MBC) showed that some of the tested ILs are very promising anti-bacterial agents especially those containing an alkyl chain with a phenyl group (most notably , , , and ).
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http://dx.doi.org/10.3390/molecules23071727DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6099736PMC
July 2018

Introducing novel potent anticancer agents of 1H-benzo[f]chromene scaffolds, targeting c-Src kinase enzyme with MDA-MB-231 cell line anti-invasion effect.

J Enzyme Inhib Med Chem 2018 Dec;33(1):1074-1088

c Chemistry Department, Faculty of Science , Al-Azhar University , Cairo , Egypt.

In our effort to develop novel and powerful agents with anti-proliferative activity, two new series of 1H-benzo[f]chromene derivatives, 4a-h and 6a-h, were synthesised using heterocyclocondensation methodologies under microwave irradiation condition. The structures of the target compounds were established on the basis of their spectral data, IR, H NMR,  C NMR,  C NMR-DEPT/APT, and MS data. The new compounds have been examined for their anti-proliferative activity against three cancer cell lines, MCF-7, HCT-116, and HepG-2. Vinblastine and Doxorubicin have been used as positive controls in the viability assay. The obtained results confirmed that most of the tested molecules revealed strong and selective cytotoxic activity against the three cancer cell lines. Moreover, these molecules exhibited weak cytotoxicity on the HFL-1 line, which suggested that they might be ideal anticancer candidates. The SAR study of the new benzochromene compounds verified that the substituents on the phenyl ring of 1H-benzo[f]chromene nucleus, accompanied with the presence of bromine atom or methoxy group at the 8-position, increases the ability of these molecules against the different cell lines. Due to their high anti-proliferative activity, compounds 4c and 6e were selected to be examined their proficiency to inhibit the invasiveness of the highly sensitive and invasive breast cancer cell line, MDA-MB-231. The anti-invasion behaviour of these molecules against the highly sensitive, non-oestrogen, and progesterone MDA-MB-231 cell line gave rise to their decreasing metastatic effect compared to the reference drug. Furthermore, this report explores the apoptotic mechanistic pathway of the cytotoxicity of the target compounds and reveals that most of these compounds enhance the Caspase 3/7 activity that could be considered as potential anticancer agents.
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http://dx.doi.org/10.1080/14756366.2018.1476503DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6022228PMC
December 2018
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