Synthesis of water-soluble 9,10-anthraquinone analogues with potent cyanobactericidal activity toward the musty-odor cyanobacterium Oscillatoria perornata.
A series of water-soluble 9,10-anthraquinone analogues were prepared and evaluated for their selective toxicity toward Oscillatoria perornata, which grows in catfish production ponds and causes "musty" off-flavor in channel catfish ( Ictalurus punctatus). Water-soluble mono- and dicationic salts were prepared by conjugating various small amines directly or through a methylene or ethylene bridge to the 9,10-anthraquinone nucleus. One of the dicationic salts, 2-[ N-(1'-methyl-4'- N, N-diethylaminobutyl)aminometyl]anthraquinone diphosphate, exhibited very high water solubility and potent selective toxicity toward O. perornata. However, the tendency of this compound to potentially bind to suspended sediments may be the reason for its limitations in controlling O. perornata in catfish production ponds. The monocationic salt, 2-[ N-(1'-methylethyl)]aminomethyl]anthraquinone monophosphate, showed good solubility and high selective toxicity toward O. perornata. Neutral water-soluble analogues prepared by conjugating terta- or pentaethylene glycol directly or by a methylene bridge to the 9,10-anthraquinone nucleus had less activity than the parent compound.
Nanayakkara
N P Dhammika
NP
Thad Cochran National Center for Natural Products Research, School of Pharmacy, Research Institute of Pharmaceutical Sciences, University of Mississippi, University, Mississippi 38677, USA. dhammika@olemiss.edu
Schrader
Kevin K
KK
D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D054300:Oscillatoria / Q000187:drug effects*; D012995:Solubility; D014867:Water
D000880:Anthraquinones; C042834:9,10-anthraquinone; D014867:Water