Abuelizz Hatem A, Taie Hanan A A, Bakheit Ahmed H, Mostafa Gamal A E, Marzouk Mohamed, Rashid Harunor, Al-Salahi Rashad
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia.
Department of Plant Biochemistry, Agriculture and Biological Research Institute, National Research Centre, 33 El-Bohouth St. (Former El-Tahrir St.), Dokki, Cairo 12622, Egypt.
ACS Omega. 2021 Nov 17;6(47):31993-32004. doi: 10.1021/acsomega.1c04772. eCollection 2021 Nov 30.
Hydrazinobenzoic acid derivatives with isothiocyanate, benzylidene, and acid anhydride core units (-) were previously synthesized and fully characterized. Targets - were investigated for their antioxidant activities using different in vitro assays such as 1,1-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging, 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonate) (ABTS), ferric reducing antioxidant power (FRAP), and reducing power capability. All derivatives showed antioxidant properties in relation to the standard butylated hydroxylanisole (BHA). Superior antioxidant activities was observed for compounds and at a concentration of 20 μg/mL (70-72%) when tested by the DPPH method in comparison to BHA (92%), and compounds showed the highest free radical quenching activity (80-85%) when examined by ABTS at 20 μg/mL in relation to BHA (85%). Density function theory (DFT) studies were carried out using the B3LYP/6-311G(d,p) level of theory. Several antioxidant descriptors were calculated for targets - compared with BHA. Targets - were proposed to exhibit their antioxidant activities via the following three proposed antioxidant mechanisms: single electron transfer (SET), hydrogen atom transfer (HAT), and sequential proton loss electron transfer (SPLET). The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energies and electron levels for - were also determined.
先前已合成并全面表征了具有异硫氰酸酯、亚苄基和酸酐核心单元（-）的肼基苯甲酸衍生物。使用不同的体外试验，如1,1-二苯基-2-苦基肼基（DPPH）自由基清除、2,2'-联氮-双-（3-乙基苯并噻唑啉-6-磺酸）（ABTS）、铁还原抗氧化能力（FRAP）和还原能力，对目标物进行了抗氧化活性研究。与标准丁基化羟基茴香醚（BHA）相比，所有衍生物均表现出抗氧化性能。通过DPPH法在20μg/mL浓度下测试时，化合物 和 观察到优于BHA（92%）的抗氧化活性（70 - 72%），并且在20μg/mL下通过ABTS检测时，化合物 相对于BHA（85%）表现出最高的自由基猝灭活性（80 - 85%）。使用B3LYP/6 - 311G(d,p)理论水平进行了密度泛函理论（DFT）研究。与BHA相比，为目标物 - 计算了几个抗氧化描述符。目标物 - 被认为通过以下三种提出的抗氧化机制表现出其抗氧化活性：单电子转移（SET）、氢原子转移（HAT）和顺序质子损失电子转移（SPLET）。还确定了 - 的最高占据分子轨道（HOMO）和最低未占据分子轨道（LUMO）能量以及电子水平。
