Semi-synthesis of phenolic-amides and their cytotoxicity against THP-1, HeLa, HepG2 and MCF-7 cell lines

Jaggaiah N. Gorantla; Sunaree Choknud; Eko Suyanto; Htun Htun Win; Yanling Hua; Maniganda Santhi; Sirilak Wangngae; Anyanee Kamkaew; Mariena Ketudat-Cairns; Lalida Rojanathammanee; James R. Ketudat Cairns

doi:10.1080/14786419.2023.2241971

Semi-synthesis of phenolic-amides and their cytotoxicity against THP-1, HeLa, HepG2 and MCF-7 cell lines

Jaggaiah N. Gorantla^*
, Sunaree Choknud
, Eko Suyanto
, Htun Htun Win
, Yanling Hua
, Maniganda Santhi
, Sirilak Wangngae
, Anyanee Kamkaew
, Mariena Ketudat-Cairns
, Lalida Rojanathammanee
, James R. Ketudat Cairns

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

Abstract

In the present study, we derivatized several hydroxycinnamic and hydroxybenzoic acids to phenolic amides (PAMs) via one step BOP mediated amide coupling reactions. Fifteen PAMs were synthesized in >40% yields and were screened for their cytotoxic activities against four cancer cell lines: THP-1 (leukaemia), HeLa (cervical), HepG2 (liver), and MCF-7 (breast), in comparison to 5-flurouracil (5-FU). Four amides showed IC₅₀ ranging from 5 to 55 µM against all four cell lines. In contrast, tetradecyl-gallic-amide (13) affected only THP-1 leukaemia cells with IC₅₀ of 3.08 µM. The activities of these compounds support the promise of phenolic amides as anticancer agents.

Original language	English
Pages (from-to)	2069-2077
Number of pages	9
Journal	Natural Product Research
Volume	38
Issue number	12
DOIs	https://doi.org/10.1080/14786419.2023.2241971
Publication status	Published - 2024
Externally published	Yes

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

MTT assay
Phenolic acid
cytotoxicity
phenolic amides (PAMs)

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10.1080/14786419.2023.2241971

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Gorantla, J. N., Choknud, S., Suyanto, E., Win, H. H., Hua, Y., Santhi, M., Wangngae, S., Kamkaew, A., Ketudat-Cairns, M., Rojanathammanee, L., & Ketudat Cairns, J. R. (2024). Semi-synthesis of phenolic-amides and their cytotoxicity against THP-1, HeLa, HepG2 and MCF-7 cell lines. Natural Product Research, 38(12), 2069-2077. https://doi.org/10.1080/14786419.2023.2241971

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title = "Semi-synthesis of phenolic-amides and their cytotoxicity against THP-1, HeLa, HepG2 and MCF-7 cell lines",

abstract = "In the present study, we derivatized several hydroxycinnamic and hydroxybenzoic acids to phenolic amides (PAMs) via one step BOP mediated amide coupling reactions. Fifteen PAMs were synthesized in >40\% yields and were screened for their cytotoxic activities against four cancer cell lines: THP-1 (leukaemia), HeLa (cervical), HepG2 (liver), and MCF-7 (breast), in comparison to 5-flurouracil (5-FU). Four amides showed IC50 ranging from 5 to 55 µM against all four cell lines. In contrast, tetradecyl-gallic-amide (13) affected only THP-1 leukaemia cells with IC50 of 3.08 µM. The activities of these compounds support the promise of phenolic amides as anticancer agents.",

keywords = "MTT assay, Phenolic acid, cytotoxicity, phenolic amides (PAMs)",

author = "Gorantla, \{Jaggaiah N.\} and Sunaree Choknud and Eko Suyanto and Win, \{Htun Htun\} and Yanling Hua and Maniganda Santhi and Sirilak Wangngae and Anyanee Kamkaew and Mariena Ketudat-Cairns and Lalida Rojanathammanee and \{Ketudat Cairns\}, \{James R.\}",

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year = "2024",

doi = "10.1080/14786419.2023.2241971",

language = "English",

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T1 - Semi-synthesis of phenolic-amides and their cytotoxicity against THP-1, HeLa, HepG2 and MCF-7 cell lines

AU - Gorantla, Jaggaiah N.

AU - Choknud, Sunaree

AU - Suyanto, Eko

AU - Win, Htun Htun

AU - Hua, Yanling

AU - Santhi, Maniganda

AU - Wangngae, Sirilak

AU - Kamkaew, Anyanee

AU - Ketudat-Cairns, Mariena

AU - Rojanathammanee, Lalida

AU - Ketudat Cairns, James R.

PY - 2024

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N2 - In the present study, we derivatized several hydroxycinnamic and hydroxybenzoic acids to phenolic amides (PAMs) via one step BOP mediated amide coupling reactions. Fifteen PAMs were synthesized in >40% yields and were screened for their cytotoxic activities against four cancer cell lines: THP-1 (leukaemia), HeLa (cervical), HepG2 (liver), and MCF-7 (breast), in comparison to 5-flurouracil (5-FU). Four amides showed IC50 ranging from 5 to 55 µM against all four cell lines. In contrast, tetradecyl-gallic-amide (13) affected only THP-1 leukaemia cells with IC50 of 3.08 µM. The activities of these compounds support the promise of phenolic amides as anticancer agents.

AB - In the present study, we derivatized several hydroxycinnamic and hydroxybenzoic acids to phenolic amides (PAMs) via one step BOP mediated amide coupling reactions. Fifteen PAMs were synthesized in >40% yields and were screened for their cytotoxic activities against four cancer cell lines: THP-1 (leukaemia), HeLa (cervical), HepG2 (liver), and MCF-7 (breast), in comparison to 5-flurouracil (5-FU). Four amides showed IC50 ranging from 5 to 55 µM against all four cell lines. In contrast, tetradecyl-gallic-amide (13) affected only THP-1 leukaemia cells with IC50 of 3.08 µM. The activities of these compounds support the promise of phenolic amides as anticancer agents.

KW - MTT assay

KW - Phenolic acid

KW - cytotoxicity

KW - phenolic amides (PAMs)

UR - https://www.scopus.com/pages/publications/85166203475

U2 - 10.1080/14786419.2023.2241971

DO - 10.1080/14786419.2023.2241971

M3 - Article

C2 - 37526601

AN - SCOPUS:85166203475

SN - 1478-6419

VL - 38

SP - 2069

EP - 2077

JO - Natural Product Research

JF - Natural Product Research

IS - 12

ER -

Semi-synthesis of phenolic-amides and their cytotoxicity against THP-1, HeLa, HepG2 and MCF-7 cell lines

Abstract

UN SDGs

Keywords

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