Cytotoxic Effects of Gallic Acid Derivatives on Hormone Dependent Breast Cancer MCF-7

Dorothea, Maya; Arsianti, Ade; Liwang, Ferry; Christian, Hans; Panjaitan, H. P.B.

doi:10.1093/annonc/mdw523.032

Cited by 4 publications

(3 citation statements)

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“…Dorothea et al ., (2016) concluded that increasing the potential for cytotoxicity to MCF7 breast cancer cells, lipophilicity must be achieved by modifying the structure of gallic acid by adding a lipophilic group to make it more hydrophobic. 15 According to in silico study, gallic acid and its derivatives (alkyl ester) can be BRAF inhibitor of colorectal cancer, 16 as well as inhibitor of the anti-apoptosis protein Bcl-xL in breast cancer. 17 , 18 In addition, gallic acid derivative compounds (N-alkyl gallamide) have strong cytotoxic activity on MCF7 breast cancer cells, and colorectal cancer cells, HCT 116.…”

Section: Introductionmentioning

confidence: 99%

Molecular docking, ADMET profiling of gallic acid and its derivatives (N-alkyl gallamide) as apoptosis agent of breast cancer MCF-7 Cells

Arsianti,

Nur Azizah,

Erlina

2024

F1000Res

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Background In 2020, breast cancer has become the most common cancer in the world and in Indonesia. Searching for anticancer drugs using computational methods is considered more effective and selective than other methods. Gallic acid and its derivatives (esters and amides) are compounds that have biological activities such as anticancer effects. The purpose of this study was to analyse the molecular modelling and ADMET (Adsorption, Distribution, Metabolism, Excretion and Toxicity) profile of gallic acid derivative compounds (N-alkyl gallamides) as anticancer agents. Methods Target proteins were selected by analysis of protein-protein and drug-protein interactions. Molecular modelling was done by molecular docking and molecular dynamic simulation. Predictive analysis of the ADMET profile of gallic acid and its derivatives (N-alkyl gallamide) was conducted using Marvin Sketch, Swissadme, protox II, and pkCSM pharmacokinetics. The selected target proteins were JUN, AKT1, CASP3, and CASP7. Results Compounds N-octyl gallamide, N-ters-butyl gallamide, and N-isoamil gallamide were the three best gallic acid derivatives based on molecular modelling analysis of target proteins associated with breast cancer. The ADMET profile of the N-alkyl gallamide compound is predictable and shows a good profile as a candidate for anticancer drugs. Conclusion N-octyl gallamide, N-ters-butyl gallamide, and N-isoamil gallamide have potential as anti-breast cancer agents.

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Section: Introductionmentioning

confidence: 99%

Molecular docking, ADMET profiling of gallic acid and its derivatives (N-alkyl gallamide) as apoptosis agent of breast cancer MCF-7 Cells

Arsianti,

Nur Azizah,

Erlina

2024

F1000Res

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“…Dorothea et al, (2016) concluded that increasing the potential for cytotoxicity to MCF7 breast cancer cells, lipophilicity must be achieved by modifying the structure of gallic acid by adding a lipophilic group to make it more hydrophobic. 15 According to in silico study, gallic acid and its derivatives (alkyl ester) can be BRAF inhibitor of colorectal cancer, 16 as well as inhibitor of the anti-apoptotic protein Bcl-xL in breast cancer. 17,18 In addition, gallic acid derivative compounds (N-alkyl gallamide) have strong cytotoxic activity on MCF7 breast cancer cells, and colorectal cancer cells, HCT 116.…”

Section: Introductionmentioning

confidence: 99%

Molecular docking, ADMET profiling of gallic acid and its derivatives (N-alkyl gallamide) as an anti-breast cancer agent

2022

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Background In 2020, breast cancer has become the most common cancer in the world and in Indonesia. Searching for anticancer drugs using computational methods is considered more effective and selective than other methods. Gallic acid and its derivatives (esters and amides) are compounds that have biological activities such as anticancer effects. The purpose of this study was to analyse the molecular modelling and ADMET (Adsorption, Distribution, Metabolism, Excretion and Toxicity) profile of gallic acid derivative compounds (N-alkyl gallamides) as anticancer agents. Methods Target proteins were selected by analysis of protein-protein and drug-protein interactions. Molecular modelling was done by molecular docking. Predictive analysis of the ADMET profile of gallic acid and its derivatives (N-alkyl gallamide) was conducted using Marvin Sketch, Swissadme, protox II, and pkCSM pharmacokinetics. The selected target proteins were JUN, AKT1, CASP3, and CASP7. Results Compounds N-octyl gallamide, N-ters-butyl gallamide, and N-isoamil gallamide were the three best gallic acid derivatives based on molecular modelling analysis of target proteins associated with breast cancer. The ADMET profile of the N-alkyl gallamide compound is predictable and shows a good profile as a candidate for anticancer drugs. Conclusion N-octyl gallamide, N-ters-butyl gallamide, and N-isoamil gallamide have potential as anti-breast cancer agents.

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“…A study has concluded that an increase in potential cytotoxicity and lipophilicity can be done by modifying the structure of gallic acid by the addition of lipophilic groups. 13 In the present study, we have done the synthesis of gallic acid derivatives as anti-hepatitis C virus agents.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anticancer Effect of 3,4,5-N-Alkyl-Benzamides on Colon Carcinoma HCT- 116 Cells

Chan

Arsianti²,

Marcelia

et al. 2018

Orient. J. Chem

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The natural phenolic gallic acid has demonstrated a significant inhibition of cell proliferation in a series of cancer cell lines, as well as induced apoptosis in HCT-116 colon cancer cells. This research aims to synthesize six compounds of 3,4,5-trihydroxy-N-alkyl-benzamide derivatives of gallic acid, and investigate its anticancer effect on colon carcinoma HCT-116 cells.Six compounds of 3,4,5-trihydroxy-N-alkyl-benzamide, namely 3,4,5-trihydroxy-N-methyl-benzamide (2); 3,4,5-trihydroxy-N-ethyl-benzamide (3); 3,4,5-trihydroxy-N-butyl-benzamide (4); 3,4,5-trihydroxy-N-sec-butyl-benzamide (5); 3,4,5-trihydroxy-N-tert-butyl-benzamide (6) and 3,4,5-trihydroxy-Nhexyl-benzamide (7), have been successfully synthesized by amidation of carboxyl group of gallic acid with six corresponding alkylamines, respectively. Furthermore, anticancer effect of these six synthesized derivatives on colon HCT-116 cells were examined by MTT assay. Data were analyzed by linear regression method to generate IC 50 value. The results will be compared with gallic acid as an original compound and doxorubicine as a positive control.Amidation of gallic acid with six corresponding alkylamines gave desired -N-methyl-, -N-ethyl-, -N-butyl-, -N-sec-butyl-, -N-ters-butyl-, and -N-hexyl benzamide with yield ranging from 18% to 84%. Compared to gallic acid (IC 50 : 0.05 µM) and doxorubicine (IC 50 : 0.001 µM), all these six synthesized derivatives showed a lower anticancer effect on colon HCT-116 cells. The strongest anticancer and inhibitory effect on HCT-116 cells has shown by 3,4,5-trihydroxy-N-hexyl benzamide (7) with IC 50 value of 0.07 µM. Our results suggested that 3,4,5-trihydroxy-N-hexyl benzamide (7) is a potential to be developed as a promising anti-colon cancer agent.

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Cytotoxic Effects of Gallic Acid Derivatives on Hormone Dependent Breast Cancer MCF-7

Cited by 4 publications

References 0 publications

Molecular docking, ADMET profiling of gallic acid and its derivatives (N-alkyl gallamide) as apoptosis agent of breast cancer MCF-7 Cells

Molecular docking, ADMET profiling of gallic acid and its derivatives (N-alkyl gallamide) as apoptosis agent of breast cancer MCF-7 Cells

Molecular docking, ADMET profiling of gallic acid and its derivatives (N-alkyl gallamide) as an anti-breast cancer agent

Synthesis and Anticancer Effect of 3,4,5-N-Alkyl-Benzamides on Colon Carcinoma HCT- 116 Cells

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