Syntheses and Cytotoxic Properties of the Curcumin Analogs 2,6-Bis(benzylidene)-4-phenylcyclohexanones

Fifteen curcumin analogs were synthesized and tested for in‐vitro cytotoxicity towards B16 and L1210 murine cancer cell lines using an MTT assay. Significant activity was discovered for two analogs: 8 (B16 IC50 = 1.6 μM; L1210 IC50 = 0.35 μM) and 9 (B16 IC50 = 0.51 μM; L1210 IC50 = 1.2 μM). Several...

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Published in:Archiv der Pharmazie (Weinheim) 2008-07, Vol.341 (7), p.440-445
Main Authors: Davis, Ryan, Das, Umashankar, Mackay, Hilary, Brown, Toni, Mooberry, Susan L., Dimmock, Jonathan R., Lee, Moses, Pati, Hari
Format: Article
Language:English
Subjects:
Animals
Antineoplastic Agents - administration & dosage
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - pharmacology
B16
Cell Line, Tumor
Curcumin - analogs & derivatives
Curcumin analogs
Cyclohexanones - administration & dosage
Cyclohexanones - chemical synthesis
Cyclohexanones - pharmacology
Drug Screening Assays, Antitumor
Inhibitory Concentration 50
L1210
Mice
Microtubules
Microtubules - drug effects
Quantitative Structure-Activity Relationship
Structure-activity relationships
Tubulin - drug effects
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cited_by cdi_FETCH-LOGICAL-c4768-6e42df1270c5def48a439d24af8e26f7ab9ace7952c45e2854dc7940e4a0a71c3
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container_issue 7
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container_title Archiv der Pharmazie (Weinheim)
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creator Davis, Ryan
Das, Umashankar
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Lee, Moses
Pati, Hari
description Fifteen curcumin analogs were synthesized and tested for in‐vitro cytotoxicity towards B16 and L1210 murine cancer cell lines using an MTT assay. Significant activity was discovered for two analogs: 8 (B16 IC50 = 1.6 μM; L1210 IC50 = 0.35 μM) and 9 (B16 IC50 = 0.51 μM; L1210 IC50 = 1.2 μM). Several other analogs exhibited notable cytotoxicity. The data from quantitative structure‐activity relationships suggest that large electron‐withdrawing substituents placed in the meta‐position of the arylidene aryl rings enhance potencies. Compounds 8 and 9 were found using a cell‐based assay to have virtually no effects on microtubules at concentrations up to 40 μM. These results suggest that tubulin inhibition is not the principal mechanism by which the curcumin analogs act.
doi_str_mv 10.1002/ardp.200800028
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subjects Animals
Antineoplastic Agents - administration & dosage
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - pharmacology
B16
Cell Line, Tumor
Curcumin - analogs & derivatives
Curcumin analogs
Cyclohexanones - administration & dosage
Cyclohexanones - chemical synthesis
Cyclohexanones - pharmacology
Drug Screening Assays, Antitumor
Inhibitory Concentration 50
L1210
Mice
Microtubules
Microtubules - drug effects
Quantitative Structure-Activity Relationship
Structure-activity relationships
Tubulin - drug effects
title Syntheses and Cytotoxic Properties of the Curcumin Analogs 2,6-Bis(benzylidene)-4-phenylcyclohexanones
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