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

Ibrahim Jantan, Bukhari Syed Nasir Abbas, Nordin Haji Lajis, Faridah Abas, Kok Wai Lam, Malina Jasamai

Research output: Contribution to journalArticle

21 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)404-412
Number of pages9
JournalJournal of Pharmacy and Pharmacology
Volume64
Issue number3
DOIs
Publication statusPublished - Mar 2012

Fingerprint

Curcumin
Respiratory Burst
Halogenation
Phagocytes
Luminescence
Cell Migration Inhibition
Luminol
Innate Immunity
Reactive Oxygen Species
Neutrophils
compound 17
compound 30
cyclohexanone
In Vitro Techniques

Keywords

  • chemiluminescence
  • chemotactic activity
  • curcumin diarylpentanoid analogues
  • immunomodulatory
  • polymorphonuclear leukocytes

ASJC Scopus subject areas

  • Pharmacology
  • Pharmaceutical Science

Cite this

Effects of diarylpentanoid analogues of curcumin on chemiluminescence and chemotactic activities of phagocytes. / Jantan, Ibrahim; Syed Nasir Abbas, Bukhari; Lajis, Nordin Haji; Abas, Faridah; Lam, Kok Wai; Jasamai, Malina.

In: Journal of Pharmacy and Pharmacology, Vol. 64, No. 3, 03.2012, p. 404-412.

Research output: Contribution to journalArticle

Jantan, Ibrahim ; Syed Nasir Abbas, Bukhari ; Lajis, Nordin Haji ; Abas, Faridah ; Lam, Kok Wai ; Jasamai, Malina. / Effects of diarylpentanoid analogues of curcumin on chemiluminescence and chemotactic activities of phagocytes. In: Journal of Pharmacy and Pharmacology. 2012 ; Vol. 64, No. 3. pp. 404-412.
@article{0decdf8d13164bb6ad49ade821ea8574,
title = "Effects of diarylpentanoid analogues of curcumin on chemiluminescence and chemotactic activities of phagocytes",
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.",
keywords = "chemiluminescence, chemotactic activity, curcumin diarylpentanoid analogues, immunomodulatory, polymorphonuclear leukocytes",
author = "Ibrahim Jantan and {Syed Nasir Abbas}, Bukhari and Lajis, {Nordin Haji} and Faridah Abas and Lam, {Kok Wai} and Malina Jasamai",
year = "2012",
month = "3",
doi = "10.1111/j.2042-7158.2011.01423.x",
language = "English",
volume = "64",
pages = "404--412",
journal = "Journal of Pharmacy and Pharmacology",
issn = "0022-3573",
publisher = "Pharmaceutical Press",
number = "3",

}

TY - JOUR

T1 - Effects of diarylpentanoid analogues of curcumin on chemiluminescence and chemotactic activities of phagocytes

AU - Jantan, Ibrahim

AU - Syed Nasir Abbas, Bukhari

AU - Lajis, Nordin Haji

AU - Abas, Faridah

AU - Lam, Kok Wai

AU - Jasamai, Malina

PY - 2012/3

Y1 - 2012/3

N2 - 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.

AB - 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.

KW - chemiluminescence

KW - chemotactic activity

KW - curcumin diarylpentanoid analogues

KW - immunomodulatory

KW - polymorphonuclear leukocytes

UR - http://www.scopus.com/inward/record.url?scp=84857059699&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84857059699&partnerID=8YFLogxK

U2 - 10.1111/j.2042-7158.2011.01423.x

DO - 10.1111/j.2042-7158.2011.01423.x

M3 - Article

C2 - 22309272

AN - SCOPUS:84857059699

VL - 64

SP - 404

EP - 412

JO - Journal of Pharmacy and Pharmacology

JF - Journal of Pharmacy and Pharmacology

SN - 0022-3573

IS - 3

ER -