Design and synthesis of novel caffeic acid phenethyl ester (CAPE) derivatives and their biological activity studies in glioblastoma multiforme (GBM) cancer cell lines

Sucu, Bilgesu Onur; Koc, Elif Beyza; İpek, Özgecan Şavluğ; Mirat, Afranur; Almas, Furkan; Guzel, Melike Aybala; Doğan, Berna; Uludağ, Damla; Karakaş, Nihal; Durdağı, Serdar; Güzel, Mustafa

doi:10.1016/j.jmgm.2022.108160

Cited by 12 publications

(9 citation statements)

References 43 publications

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“…The results showed that compared with CAPE, compound 72 ( Figure 5 ) up to 50 μM significantly reduced the viability of T98G and LN229 cells with IC 50 values of 46.42 and 14.23 μM, respectively. Furthermore, the same concentration of compound 72 was not cytotoxic to healthy human cells (fibroblast-like mesenchymal stem cells) 75 .…”

Section: Oxadiazolementioning

confidence: 93%

Research progress on the synthesis and pharmacology of 1,3,4-oxadiazole and 1,2,4-oxadiazole derivatives: a mini review

Wang

Sun

Jia

et al. 2022

Journal of Enzyme Inhibition and Medicinal Chemistry

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Oxadiazole is a five-membered heterocyclic compound containing two nitrogen atoms and one oxygen atom. The 1,3,4-oxadiazole and 1,2,4-oxadiazole have favourable physical, chemical, and pharmacokinetic properties, which significantly increase their pharmacological activity via hydrogen bond interactions with biomacromolecules. In recent years, oxadiazole has been demonstrated to be the biologically active unit in a number of compounds. Oxadiazole derivatives exhibit antibacterial, anti-inflammatory, anti-tuberculous, anti-fungal, anti-diabetic and anticancer activities. In this paper, we report a series of compounds containing oxadiazole rings that have been published in the last three years only (2020–2022) as there was no report or their activities described in any article in 2019, which will be useful to scientists in research fields of organic synthesis, medicinal chemistry, and pharmacology.

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Section: Oxadiazolementioning

confidence: 93%

Research progress on the synthesis and pharmacology of 1,3,4-oxadiazole and 1,2,4-oxadiazole derivatives: a mini review

Wang

Sun

Jia

et al. 2022

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…A recent survey showed that around 3.2 cases per 1 lakh of population per year suffering from GBM and also showed a remarkably poor prognosis with only 26-33 % survival rate in 2 years and around 5 % survival in 5 years. [1][2][3][4][5][6][7][8][9][10][11][12] A significant progress has been made in making drugs for brain cancer or similar cancer through radiation therapy, resection techniques and chemotherapy but the survival of the median patient is significantly lower. [9,17] This short survival rate under modern medication forces us to further study the process of Glioblastoma Malignant with a better understanding.…”

Section: Introductionmentioning

confidence: 99%

“…The World Health Organization (WHO) classifies glioblastoma multiforme (GBM) become the most prevalent and fatal subset of brain tumours as a grade IV astrocytoma. A recent survey showed that around 3.2 cases per 1 lakh of population per year suffering from GBM and also showed a remarkably poor prognosis with only 26–33 % survival rate in 2 years and around 5 % survival in 5 years [1–12] . A significant progress has been made in making drugs for brain cancer or similar cancer through radiation therapy, resection techniques and chemotherapy but the survival of the median patient is significantly lower [9,17] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, Molecular Docking and in vitro Anticancer Screening of Some Novel Thiophene Derivatives

Patel

et al. 2023

ChemistrySelect

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One of the diseases in the 21 st century is still cancer and there is significant research being done all over the world to find a medicine that is more effective and has fewer adverse effects. More than 19 million new cases of cancer have been reported by global statistics and an estimated 10 million people have died from it in 2020. We continue to work on the development of new pharmacological entities because we are motivated in the research area. We have created novel thiophene derivatives and have screened them against the U87-MG cell line to see whether they have any anticancer properties. It was observed that the AP-C12 extract showed the highest inhibition in the U87-MG cell line (EC 50 : 9.1 μM) which was a very good comparison to Temozolomide (EC 50 : 61.2 μM). Similarly, AP-C7 exhibited considerable potency against the U87-MG cell line with EC 50 values of 12.3 μM.

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“…The phenylpropanoid scaffold of CA and FA is used to synthesize many biologically active molecules [25] . We have shown in our initial studies that the compounds in which we replaced the acid/ester group with the heterocyclic core gave more active results against GB cell lines [26] . Based on the results of this study, we have examined the activity relationship by deriving compounds containing oxadiazoles and obtained active results against different cell lines [27] .…”

Section: Introductionmentioning

confidence: 99%

“…[25] We have shown in our initial studies that the compounds in which we replaced the acid/ester group with the heterocyclic core gave more active results against GB cell lines. [26] Based on the results of this study, we have examined the activity relationship by deriving compounds containing oxadiazoles and obtained active results against different cell lines. [27] When the structure-activity results of the derivatives are examined, it is predicted that various heterocyclic structures will increase the activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antiproliferative Evaluation of New 1,3,5‐Trisubstituted 1,2,4‐Triazole Derivatives against Glioblastoma Cell Lines

Koc

Sucu

2023

ChemistrySelect

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A series of novel 1,3,5-trisubstituted-1,2,4-triazole derivatives were successfully synthesized from the starting materials of caffeic acid (CA) and ferulic acid (FA) in moderate to good yields (45-71 %). All novel compounds were screened for antiproliferative activity against three glioblastoma (GB) cell lines. Several compounds exhibited improved cytotoxic activities compared to the caffeic acid phenethyl ester (CAPE). Among the novel derivatives, 4-(2-(1-benzyl-3-phenyl-1H-1,2,4triazol-5-yl)vinyl)-2-methoxyphenol (4) exhibited the most potent activity against the U87G, T98G and LN229 cell lines.Western blot results showed significantly reduced poly(ADPribose) polymerase (PARP) and increased the Bcl-2-associated X (Bax) protein levels in T98G cells. Also, flow cytometry results using Annexin-V/Propidium Iodide (PI) staining indicated that apoptosis was induced in T98G cells. It was found to be a promising drug candidate with strong physicochemical and bioavailability properties as a result of SwissADME calculations. These results show that novel compounds containing a 1,2,4triazole moiety have a good antiproliferative activity on GB cells.

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Design and synthesis of novel caffeic acid phenethyl ester (CAPE) derivatives and their biological activity studies in glioblastoma multiforme (GBM) cancer cell lines

Cited by 12 publications

References 43 publications

Research progress on the synthesis and pharmacology of 1,3,4-oxadiazole and 1,2,4-oxadiazole derivatives: a mini review

Research progress on the synthesis and pharmacology of 1,3,4-oxadiazole and 1,2,4-oxadiazole derivatives: a mini review

Synthesis, Characterization, Molecular Docking and in vitro Anticancer Screening of Some Novel Thiophene Derivatives

Synthesis and Antiproliferative Evaluation of New 1,3,5‐Trisubstituted 1,2,4‐Triazole Derivatives against Glioblastoma Cell Lines

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