Design, Synthesis, and Characterization of Cinnamic Acid Derivatives with Two Novel Acrylohydrazones on HeLa and CHO-1 Cancer Cell Lines: The Experimental and Computational Perspective

Ogunlakin, Akingbolabo Daniel; Sonibare, Mubo Adeola; Yeye, Oloruntoba Emmanuel; Jabeen, Almas; Shah, Syeda Farah; Ojo, Oluwafemi Adeleke; Gyebi, Gideon Ampoma; Ayokunle, Damilare IyinKristi

doi:10.1007/s42250-023-00770-9

Cited by 1 publication

(4 citation statements)

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“…KAD-7 (N -(2,4-dichlorobenzylidene)-3-(4-methoxyphenyl) acrylohydrazide), synthesized from cinnamic acid by Ogunlakin [5], was used in this study. Quercetin was made by SantaCruz Biotechnology, which is based in Heidelberg, Germany.…”

Section: Chemicalsmentioning

confidence: 99%

“…Among its other pharmacological properties, cinnamic acid and its derivatives are reported to ameliorate diabetes and its complications as they are reported to exhibit hypoglycemic and antioxidant activities. The mechanism of its antidiabetic action includes gluconeogenesis inhibition, stimulation of insulin secretion, stimulation of glucose absorption, and delay of carbohydrate digestion, among others [3,5]. These compounds demonstrate their antioxidant activity by preventing the cleavage of hydrogen ions, which results in the neutralization of free radicals [3,5].…”

Section: Introductionmentioning

confidence: 99%

“…The mechanism of its antidiabetic action includes gluconeogenesis inhibition, stimulation of insulin secretion, stimulation of glucose absorption, and delay of carbohydrate digestion, among others [3,5]. These compounds demonstrate their antioxidant activity by preventing the cleavage of hydrogen ions, which results in the neutralization of free radicals [3,5]. Ogunlakin et al [5] reported the effect of KAD-7, a derivative of cinnamic acid, on the proliferation of the CHO-1 and HeLa cell lines (with abnormal p53 tumour suppressor gene).…”

Section: Introductionmentioning

confidence: 99%

“…These compounds demonstrate their antioxidant activity by preventing the cleavage of hydrogen ions, which results in the neutralization of free radicals [3,5]. Ogunlakin et al [5] reported the effect of KAD-7, a derivative of cinnamic acid, on the proliferation of the CHO-1 and HeLa cell lines (with abnormal p53 tumour suppressor gene). The backbone structure of KAD-7 (Figures S1 and S2), which has hydrazones, has been the focus of substantial investigation in recent years due to its numerous features and possible uses in the areas of pharmaceutical, chemical, and analytical chemistry [6].…”

Section: Introductionmentioning

confidence: 99%

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Therapeutic Study of Cinnamic Acid Derivative for Oxidative Stress Ablation: The Computational and Experimental Answers

Ojo,

Ogunlakin,

Maimako

et al. 2023

Molecules

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This study aimed to examine the therapeutic activity of the cinnamic acid derivative KAD-7 (N′-(2,4-dichlorobenzylidene)-3-(4-methoxyphenyl) acrylohydrazide) on Fe2+-induced oxidative hepatic injury via experimental and computational models. In addition, the role of ATPase and ectonucleoside triphosphate diphosphohydrolase (ENTPDase) in the coordination of cellular signals is speculated upon to proffer suitable therapeutics for metabolic stress disorder upon their inhibition. While we know little about therapeutics with flexible dual inhibitors for these protein targets, this study was designed to screen KAD-7’s (N′-(2,4-dichlorobenzylidene)-3-(4-methoxyphenyl) acrylohydrazide) inhibitory potential for both protein targets. We induced oxidative hepatic damage via the incubation of hepatic tissue supernatant with 0.1 mM FeSO4 for 30 min at 37 °C. We achieved the treatment by incubating the hepatic tissues with KAD-7 under the same conditions. The catalase (CAT), glutathione (GSH), malondialdehyde (MDA), ATPase, and ENTPDase activity were all measured in the tissues. We predicted how the drug candidate would work against ATPase and ENTPDase targets using molecular methods. When hepatic injury was induced, there was a significant decrease in the levels of the GSH, CAT, and ENTPDase (p < 0.05) activities. In contrast, we found a noticeable rise in the MDA levels and ATPase activity. KAD-7 therapy resulted in lower levels of these activities overall (p < 0.05), as compared to the control levels. We found the compound to have a strong affinity for ATPase (−7.1 kcal/mol) and ENTPDase (−7.4 kcal/mol), and a better chemical reactivity than quercetin. It also met all drug-likeness parameters. Our study shows that KAD-7 can protect the liver from damage caused by FeSO4 by reducing oxidative stress and purinergic actions. Our studies indicate that KAD-7 could be developed as a therapeutic option since it can flexibly inhibit both ATPase and ENTPDase.

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Section: Chemicalsmentioning

confidence: 99%