Design and synthesis of novel pipernonaline derivatives as anti-austerity agents against human pancreatic cancer PANC-1 cells

Takuya Okada; Yuri Chino; Keita Yokoyama; Yuki Fujihashi; Nguyễn Duy Phan; Juthamart Maneenet; Lanke Prudhvi; Suresh Awale; Naoki Toyooka

doi:10.1016/j.bmc.2022.116963

Design and synthesis of novel pipernonaline derivatives as anti-austerity agents against human pancreatic cancer PANC-1 cells

Takuya Okada^*, Yuri Chino, Keita Yokoyama, Yuki Fujihashi, Nguyễn Duy Phan, Juthamart Maneenet, Lanke Prudhvi, Suresh Awale, Naoki Toyooka

^*Corresponding author for this work

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

7 Scopus citations

Abstract

Pipernonaline (1), one of the components of the spice pepper, preferentially reduced the survival of human pancreatic cancer PANC-1 cells under nutrient-deprived conditions with a PC₅₀ value of 7.2 μM, suggesting that 1 could potentially lead to the development of new anticancer agents based on the anti-austerity strategy. We have synthesized a total of 31 pipernonaline derivatives, revealing clear structure–activity relationships. Compound 9, which showed the strongest preferential cytotoxicity among synthesized derivatives, inhibited Akt activation and cancer cell migration, making it an extremely promising candidate compound for new pancreatic cancer agents based on the anti-austerity strategy.

Original language	English
Article number	116963
Journal	Bioorganic and Medicinal Chemistry
Volume	71
DOIs	https://doi.org/10.1016/j.bmc.2022.116963
State	Published - 2022/10/01

Keywords

Anti-austerity strategy
Pancreatic cancer
Pipernonaline
Structure-activity relationship

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmc.2022.116963

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title = "Design and synthesis of novel pipernonaline derivatives as anti-austerity agents against human pancreatic cancer PANC-1 cells",

abstract = "Pipernonaline (1), one of the components of the spice pepper, preferentially reduced the survival of human pancreatic cancer PANC-1 cells under nutrient-deprived conditions with a PC50 value of 7.2 μM, suggesting that 1 could potentially lead to the development of new anticancer agents based on the anti-austerity strategy. We have synthesized a total of 31 pipernonaline derivatives, revealing clear structure–activity relationships. Compound 9, which showed the strongest preferential cytotoxicity among synthesized derivatives, inhibited Akt activation and cancer cell migration, making it an extremely promising candidate compound for new pancreatic cancer agents based on the anti-austerity strategy.",

keywords = "Anti-austerity strategy, Pancreatic cancer, Pipernonaline, Structure-activity relationship",

author = "Takuya Okada and Yuri Chino and Keita Yokoyama and Yuki Fujihashi and {Duy Phan}, Nguyễn and Juthamart Maneenet and Lanke Prudhvi and Suresh Awale and Naoki Toyooka",

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doi = "10.1016/j.bmc.2022.116963",

language = "英語",

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journal = "Bioorganic and Medicinal Chemistry",

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TY - JOUR

T1 - Design and synthesis of novel pipernonaline derivatives as anti-austerity agents against human pancreatic cancer PANC-1 cells

AU - Okada, Takuya

AU - Chino, Yuri

AU - Yokoyama, Keita

AU - Fujihashi, Yuki

AU - Duy Phan, Nguyễn

AU - Maneenet, Juthamart

AU - Prudhvi, Lanke

AU - Awale, Suresh

AU - Toyooka, Naoki

PY - 2022/10/1

Y1 - 2022/10/1

N2 - Pipernonaline (1), one of the components of the spice pepper, preferentially reduced the survival of human pancreatic cancer PANC-1 cells under nutrient-deprived conditions with a PC50 value of 7.2 μM, suggesting that 1 could potentially lead to the development of new anticancer agents based on the anti-austerity strategy. We have synthesized a total of 31 pipernonaline derivatives, revealing clear structure–activity relationships. Compound 9, which showed the strongest preferential cytotoxicity among synthesized derivatives, inhibited Akt activation and cancer cell migration, making it an extremely promising candidate compound for new pancreatic cancer agents based on the anti-austerity strategy.

AB - Pipernonaline (1), one of the components of the spice pepper, preferentially reduced the survival of human pancreatic cancer PANC-1 cells under nutrient-deprived conditions with a PC50 value of 7.2 μM, suggesting that 1 could potentially lead to the development of new anticancer agents based on the anti-austerity strategy. We have synthesized a total of 31 pipernonaline derivatives, revealing clear structure–activity relationships. Compound 9, which showed the strongest preferential cytotoxicity among synthesized derivatives, inhibited Akt activation and cancer cell migration, making it an extremely promising candidate compound for new pancreatic cancer agents based on the anti-austerity strategy.

KW - Anti-austerity strategy

KW - Pancreatic cancer

KW - Pipernonaline

KW - Structure-activity relationship

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U2 - 10.1016/j.bmc.2022.116963

DO - 10.1016/j.bmc.2022.116963

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AN - SCOPUS:85135869167

SN - 0968-0896

VL - 71

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

M1 - 116963

ER -

Design and synthesis of novel pipernonaline derivatives as anti-austerity agents against human pancreatic cancer PANC-1 cells

Abstract

Keywords

ASJC Scopus subject areas

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