Structure-activity relationship study of growth inhibitory 2-styrylchromones against carcinoma cells

Chen Lin; Pei Jung Lu; Chia Ning Yang; Christopher Hulme; Arthur Y. Shaw

doi:10.1007/s00044-012-0232-6

Structure-activity relationship study of growth inhibitory 2-styrylchromones against carcinoma cells

Chen Lin, Pei Jung Lu, Chia Ning Yang, Christopher Hulme, Arthur Y. Shaw

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

13 Scopus citations

Abstract

The structure-activity relationship study of 2-styrylchromones against carcinoma cell growth is discussed in the present report. Taking advantage of 2-styrylchromone as a molecular template, a series of structural modifications was carried out and examined on several carcinoma cell lines. Interestingly, AGS cells exhibited more sensitivity in response to methoxy-bearing compounds, of which compound 23 (3,4,5-trimethoxy group on ring B) showed the most potent activity with a GI₅₀ value of 1.3 μM. Surprisingly, as methoxy groups in 12 and 24-27 were demethylated to generate their hydroxyl counterparts 28-32, none of them displayed appreciable activity against all carcinoma cells. We further confirmed the pivotal role of rigidity for growth inhibitory activity between the rigid 12 and its flexible counterpart 33. Taken together, in the present report, we have clearly demonstrated the structure-activity relationship study of 2-styrylchromones targeting carcinoma cell growth.

Original language	English (US)
Pages (from-to)	2385-2394
Number of pages	10
Journal	Medicinal Chemistry Research
Volume	22
Issue number	5
DOIs	https://doi.org/10.1007/s00044-012-0232-6
State	Published - May 2013

Keywords

2-Styrylchromone
Carcinoma cells
Growth inhibition
Structure-activity relationship study

ASJC Scopus subject areas

General Pharmacology, Toxicology and Pharmaceutics
Organic Chemistry

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10.1007/s00044-012-0232-6

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title = "Structure-activity relationship study of growth inhibitory 2-styrylchromones against carcinoma cells",

abstract = "The structure-activity relationship study of 2-styrylchromones against carcinoma cell growth is discussed in the present report. Taking advantage of 2-styrylchromone as a molecular template, a series of structural modifications was carried out and examined on several carcinoma cell lines. Interestingly, AGS cells exhibited more sensitivity in response to methoxy-bearing compounds, of which compound 23 (3,4,5-trimethoxy group on ring B) showed the most potent activity with a GI50 value of 1.3 μM. Surprisingly, as methoxy groups in 12 and 24-27 were demethylated to generate their hydroxyl counterparts 28-32, none of them displayed appreciable activity against all carcinoma cells. We further confirmed the pivotal role of rigidity for growth inhibitory activity between the rigid 12 and its flexible counterpart 33. Taken together, in the present report, we have clearly demonstrated the structure-activity relationship study of 2-styrylchromones targeting carcinoma cell growth.",

keywords = "2-Styrylchromone, Carcinoma cells, Growth inhibition, Structure-activity relationship study",

author = "Chen Lin and Lu, {Pei Jung} and Yang, {Chia Ning} and Christopher Hulme and Shaw, {Arthur Y.}",

note = "Funding Information: Acknowledgments Financial support from the National Science Council of the Republic of China and Tamkang University to A. Y. Shaw is gratefully acknowledged.",

year = "2013",

month = may,

doi = "10.1007/s00044-012-0232-6",

language = "English (US)",

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pages = "2385--2394",

journal = "Medicinal Chemistry Research",

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T1 - Structure-activity relationship study of growth inhibitory 2-styrylchromones against carcinoma cells

AU - Lin, Chen

AU - Lu, Pei Jung

AU - Yang, Chia Ning

AU - Hulme, Christopher

AU - Shaw, Arthur Y.

N1 - Funding Information: Acknowledgments Financial support from the National Science Council of the Republic of China and Tamkang University to A. Y. Shaw is gratefully acknowledged.

PY - 2013/5

Y1 - 2013/5

N2 - The structure-activity relationship study of 2-styrylchromones against carcinoma cell growth is discussed in the present report. Taking advantage of 2-styrylchromone as a molecular template, a series of structural modifications was carried out and examined on several carcinoma cell lines. Interestingly, AGS cells exhibited more sensitivity in response to methoxy-bearing compounds, of which compound 23 (3,4,5-trimethoxy group on ring B) showed the most potent activity with a GI50 value of 1.3 μM. Surprisingly, as methoxy groups in 12 and 24-27 were demethylated to generate their hydroxyl counterparts 28-32, none of them displayed appreciable activity against all carcinoma cells. We further confirmed the pivotal role of rigidity for growth inhibitory activity between the rigid 12 and its flexible counterpart 33. Taken together, in the present report, we have clearly demonstrated the structure-activity relationship study of 2-styrylchromones targeting carcinoma cell growth.

AB - The structure-activity relationship study of 2-styrylchromones against carcinoma cell growth is discussed in the present report. Taking advantage of 2-styrylchromone as a molecular template, a series of structural modifications was carried out and examined on several carcinoma cell lines. Interestingly, AGS cells exhibited more sensitivity in response to methoxy-bearing compounds, of which compound 23 (3,4,5-trimethoxy group on ring B) showed the most potent activity with a GI50 value of 1.3 μM. Surprisingly, as methoxy groups in 12 and 24-27 were demethylated to generate their hydroxyl counterparts 28-32, none of them displayed appreciable activity against all carcinoma cells. We further confirmed the pivotal role of rigidity for growth inhibitory activity between the rigid 12 and its flexible counterpart 33. Taken together, in the present report, we have clearly demonstrated the structure-activity relationship study of 2-styrylchromones targeting carcinoma cell growth.

KW - 2-Styrylchromone

KW - Carcinoma cells

KW - Growth inhibition

KW - Structure-activity relationship study

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JO - Medicinal Chemistry Research

JF - Medicinal Chemistry Research

IS - 5

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Structure-activity relationship study of growth inhibitory 2-styrylchromones against carcinoma cells

Abstract

Keywords

ASJC Scopus subject areas

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