Volume 64, Issue 3 pp. 404-412

Effects of diarylpentanoid analogues of curcumin on chemiluminescence and chemotactic activities of phagocytes

Ibrahim Jantan

Corresponding Author

Ibrahim Jantan

Drug and Herbal Research Center, Faculty of Pharmacy, Universiti Kebangsaan Malaysia, Kuala Lumpur

Ibrahim Jantan, Drug and Herbal Research Center, Faculty of Pharmacy, Universiti Kebangsaan Malaysia, Jalan Raja Muda Abdul Aziz, 50300 Kuala Lumpur, Malaysia. E-mail: [email protected]Search for more papers by this author
Syed Nasir Abbas Bukhari

Syed Nasir Abbas Bukhari

Drug and Herbal Research Center, Faculty of Pharmacy, Universiti Kebangsaan Malaysia, Kuala Lumpur

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Nordin Haji Lajis

Nordin Haji Lajis

Institute of Bioscience, Universiti Putra Malaysia, Selangor, Malaysia

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Faridah Abas

Faridah Abas

Institute of Bioscience, Universiti Putra Malaysia, Selangor, Malaysia

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Lam Kok Wai

Lam Kok Wai

Drug and Herbal Research Center, Faculty of Pharmacy, Universiti Kebangsaan Malaysia, Kuala Lumpur

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Malina Jasamai

Malina Jasamai

Drug and Herbal Research Center, Faculty of Pharmacy, Universiti Kebangsaan Malaysia, Kuala Lumpur

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First published: 16 December 2011
Citations: 25

Abstract

Objectives A series of 43 curcumin diarylpentanoid analogues were synthesized and evaluated for their inhibitory effects on the chemiluminescence and chemotactic activity of phagocytes in vitro.

Methods The effects of the compounds on the respiratory burst of human whole blood and isolated human polymorphonuclear leukocytes (PMNs) were evaluated using a luminol-based chemiluminescence assay and their effect on chemotactic migration of PMNs was investigated using the Boyden chamber technique.

Key findings Compounds 6, 17, 25 and 30 exhibited significant inhibitory activity on the oxidative burst of PMNs. The presence of methoxy groups at positions 2 and 5, and methoxylation and fluorination at positions 4 and 2 of both phenyl rings, respectively, may contribute significantly to their reactive oxygen species inhibition activity. Compounds 7, 17, 18, 24 and 32 showed strong inhibition of the chemotaxis migration of PMNs. Chlorination at various positions of both phenyl rings of cyclohexanone diarylpentanoid resulted in compounds with potent inhibitory effects on PMN migration.

Conclusions The results suggest that some of these diarylpentanoid analogues are able to modulate the innate immune response of phagocytes at different steps, emphasizing their potential as a source of new immunomodulatory agents.

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