In-vitro cytotoxic activities of the major bromophenols of the red alga Polysiphonia lanosa and some novel synthetic isomers.
Bioassay-guided fractionation was applied to the cytotoxic chloroform fraction of the red alga Polysiphonia lanosa. The major compounds of the most active fraction were identified using GLC-MS analysis as lanosol (1), methyl, ethyl, and n-propyl ethers of lanosol (1a, 1b, and 1c, respectively), and aldehyde of lanosol (2), although 1b appears to be an artifact arising during the fractionation procedure. These compounds and other known bromophenols were synthesized in addition to four novel isomers (3, 3a-c). The cytotoxic activities of all the synthetic compounds were determined against DLD-1 cells using the MTT assay. Compounds with IC(50) < 20 micromol were also tested against HCT-116 cells. Compound 3c (2,5-dibromo-3,4-dihydroxybenzyl n-propyl ether) was the most active compound against both cell lines (IC(50) = 1.72 and 0.80 micromol, respectively), and its effect on the cell cycle was studied using flow cytometry.
Shoeib
Nagwa A
NA
The School of Pharmacy and Tom Connors Cancer Research Centre, University of Bradford, West Yorkshire, BD7 1DP, UK.
Bibby
Michael C
MC
Blunden
Gerald
G
Linley
Peter A
PA
Swaine
David J
DJ
Wheelhouse
Richard T
RT
Wright
Colin W
CW
D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D004739:England; D006842:Hydrocarbons, Brominated / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D007536:Isomerism; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010636:Phenols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000461:Rhodophyta; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D006842:Hydrocarbons, Brominated; D010636:Phenols