Synthesis and evaluation of chalcone derivatives as inhibitors of neutrophils' chemotaxis, phagocytosis and production of reactive oxygen species

Chemical Biology and Drug Design

Volumn 83, Issue 2, 2014, Pages 198-206

  Bukhari, Syed N A ^a   Tajuddin, Yasmin ^a   Benedict, Vannessa J ^a   Lam, Kok W ^a   Jantan, Ibrahim ^a   Jalil, Juriyati ^a   Jasamai, Malina ^a  

^a UNIVERSITI KEBANGSAAN MALAYSIA   (Malaysia)

Author keywords

chalcones; chemotaxis; inhibitors; phagocytosis; reactive oxygen species; structure activity relationship

Indexed keywords

1,1,5 TRIPHENYL 3 HEXEN 2 ONE; 2',4',6' TRIMETHOXY 4 (2,3 DIMETHOXY) CHALCONE; 2',4',6' TRIMETHOXY 4 METHYLAMINOETHANOL CHALCONE; 3 (2,4 DIMETHOXYPHENYL) 1 DIPHENYL 2 PROPEN 1 ONE; 3 (4 DIETHYLAMINOPHENYL) 1 DIPHENYL 2 PROPEN 1 ONE; 3 (4 METHYAMINOETHANOLPHENYL) 1 (2 FURYL) 2 PROPEN 1 ONE; 3 (4 METHYAMINOETHANOLPHENYL) 1 (5 METHYL 2 FURYL) 2 PROPEN1 ONE; 3 (4 METHYAMINOETHANOLPHENYL) 1 (NAPHTHALEN 1 YL) 2 PROPEN 1 ONE; 3 (4 METHYAMINOETHANOLPHENYL) 1 DIPHENYL 2 PROPEN 1 ONE; 3 (4 TERT BUTYL PHENYL) 1 (NAPHTHALEN 1 YL) 2 PROPEN 1 ONE; 3 (5 METHYL 2 FURYL) 1 (NAPHTHALEN 1 YL) 2 PROPEN 1 ONE; ACETYLSALICYLIC ACID; CHALCONE DERIVATIVE; CHEMOTAXIS INHIBITOR; IBUPROFEN; IMMUNOMODULATING AGENT; LUCIGENIN; LUMINOL; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG;

ARTICLE; CELL MIGRATION; CELL PHAGOCYTOSIS; CELL VIABILITY; CHEMOLUMINESCENCE; CHEMOTAXIS ASSAY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; NEUTROPHIL; NEUTROPHIL CHEMOTAXIS; PHAGOCYTOSIS; PRIORITY JOURNAL;

CHALCONES; CHEMOTAXIS; INHIBITORS; PHAGOCYTOSIS; REACTIVE OXYGEN SPECIES; STRUCTURE-ACTIVITY RELATIONSHIP;

ANTI-INFLAMMATORY AGENTS; CELL SURVIVAL; CHALCONE; CHEMOTAXIS, LEUKOCYTE; ETHANOLAMINES; HUMANS; IMMUNOSUPPRESSIVE AGENTS; NEUTROPHILS; PHAGOCYTOSIS; REACTIVE OXYGEN SPECIES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84892497471     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/cbdd.12226     Document Type: Article

References (30)

1. Van Haastert P.J.M., Devreotes P.N., (2004) Chemotaxis: signalling the way forward. Nat Rev Mol Cell Bio; 5: 626-634.
2. McKenzie S.E., Schreiber A.D., (1998) Fc gamma receptors in phagocytes. Curr Opin Hematol; 5: 16-21.
3. Smith J.A., (1994) Neutrophils, host defense and inflammation: a double sword. J Leukocyte Biol; 56: 672-686.
4. Babior B.M., (1992) The respiratory burst oxidase. Adv Enzymol; 65: 49-95.
5. Weiss S.J., (1989) Tissue destruction by neutrophils. N Eng J Med; 320: 365-376.
6. Robinson J., Watson F., Bucknall R.C., Edwards S.W., (1992) Activation of neutrophil reactive oxidant production by synovial fluid from patients with inflammatory joint disease: soluble and insoluble immunoglobulin aggregates activate different pathways in primed and unprimed cells. Biochem J; 286: 345-351.
7. Opdenakker G., Van Damme J., (1992) Cytokines and proteases in invasive processes: molecular similarities between inflammation and cancer. Cytokine; 4: 251-258.
8. Scaccini C., Jialah I., (1994) LDL modification by activated polymorphonuclear leukocytes: a cellular model of mild oxidative stress. Free Radicals Biol Med; 16: 49-55.
9. Wallace J.L., Keenan C.M., Granger D.N., (1990) Gastric ulceration induced by nonsteroidal anti-inflammatory drugs is a neutrophil-dependent process. Am J Physiol-Gastr L; 259: 462-467.
10. Staatz C.E., Tett S.E., (2005) Pharmacokinetic considerations relating to tacrolimus dosing in the elderly. Drug Aging; 22: 541-557.
11. Gerhauser C., Alt A., Heiss E., Gamal-Eldeen A., Klimo K., Knauft J., Neumann I., Scherf H.R., Frank N., Bartsch H., Becker H., (2002) Cancer chemopreventive activity of xanthohumol, a natural product derived from hop. Mol Cancer Ther; 1: 959-969.
12. CIP1/WAF1 expression in human lung cancer cells by isoliquiritigenin. Cancer Lett; 207: 27-35.
13. Song N.J., Yoon H.J., Kim K.H., Jung S.R., Jang W.S., Seo C.R., Lee Y.M., Kweon D.H., Hong J.W., Lee J.S., Park K.M., Lee K.R., Park K.W., (2013) Butein is a novel anti-adipogenic compound. J Lipid Res; 54: 1385-1396.
14. Won S.J., Liu C.T., Tsao L.T., Weng J.R., Ko H.H., Wang J.P., Lin C.N., (2005) Synthetic chalcones as potential anti-inflammatory and cancer chemopreventive agents. Eur J Med Chem; 40: 103-112.
15. Nowakowska Z., Kȩdzia B., Schroeder G., (2008) Synthesis, physicochemical properties and antimicrobial evaluation of new (E)-chalcones. Eur J Med Chem; 43: 707-713.
16. Tomar V., Bhattacharjee G., Kumar K., Kumar A., (2007) Synthesis and antimicrobial evaluation of new chalcones containing piperazine or 2,5-dichlorothiophene moiety. Bioorgan Med Chem; 17: 5321-5324.
17. Katsori A.M., Hadjipavlou-Litina D., (2009) Chalcones in cancer: understanding their role in terms of QSAR. Curr Med Chem; 16: 1062-1081.
18. Abbas Bukhari S.N., Jantan I., Jasamai M., (2013) Anti-inflammatory trends of 1,3-diphenyl-2-propen-1-one derivatives. Mini-Rev Med Chem; 13: 87-94.
19. Sawle P., Moulton B.E., Jarzykowska M., Green C.J., Foresti R., Fairlamb I.J.S., Motterlini R., (2008) Structure-Activity Relationships of Methoxychalcones as Inducers of Heme Oxygenase-1. Chem Res Toxicol; 21: 1484-1494.
20. Chiaradia L.D., dos Santos R., Vitor C.E., Vieira A.A., Leal P.C., Nunes R.J., Calixto J.B., Yunes R.A., (2008) Synthesis and pharmacological activity of chalcones derived from 2,4,6-trimethoxyacetophenone in RAW 264.7 cells stimulated by LPS: Quantitative structure-activity relationships. Bioorgan Med Chem; 16: 658-667.
21. Jin F., Jin X.Y., Jin Y.L., Sohn D.W., Kim S.A., Sohn D.H., Kim Y.C., Kim H.S., (2007) Structural requirements of 2′,4′,6′- tris(methoxymethoxy) chalcone derivatives for anti-inflammatory activity: the importance of a 2′-hydroxy moiety. Arch Pharm Res; 30: 1359-1367.
22. Lam K.W., Uddin R., Liew C.Y., Tham C.L., Israf D.A., Syahida A., Abdul Rahman B.S., Ul-Haq Z., Lajis N.H., (2012) Synthesis and QSAR analysis of chalcone derivatives as nitric oxide inhibitory agent. Med Chem Res; 21: 1953-1966.
23. Misra S.S., Tewari R.S., (1971) Antibacterial agents V. Naphthalene chalcone analogs. Indian J App Chem; 34: 211-213.
24. Jantan I., Abbas Bukhari S.N., Lajis N.H., Abas F., Wai L.K., Jasamai M., (2012) Effects of diarylpentanoid analogues of curcumin on chemiluminescence and chemotactic activities of phagocytes. J Pharm Pharmacol; 64: 404-412.
25. Operators Manual Phagotest®, 7/96, 1-8.
26. Pavia D.L., Lampman G.M., Kriz G.S., Vyvyan J.R., (2009) Introduction to Spectroscopy. Belmont: Brooks/Cole.
27. Stuhlmeier K.M., Li H., Kao J.J., (1999) Ibuprofen: new explanation for an old phenomenon. Biochem Pharmacol; 57: 313-320.
28. Parij N., Nagy A.M., Fondu P., Nève J., (1998) Effects of non-steroidal anti-inflammatory drugs on the luminol and lucigenin amplified chemiluminescence of human neutrophils. Eur J Phamacol; 352: 299-305.
29. Lipinski C.A., Lombardo F., Dominy B.W., Feeney P.J., (1997) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Delivery Rev; 23: 3-25.
30. Ertl P., Rohde B., Selzer P., (2000) Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties. J Med Chem; 43: 3714-3717.