Study of pro- and anti-oxidative properties of D-penicillamine in a system comprising high-molar-mass hyaluronan, ascorbate, and cupric ions.
OBJECTIVE
The study presents results of pro- and anti-oxidative effects of D-penicillamine on hyaluronan degradation by ascorbate plus cupric ions.


METHODS
The well established degradative system comprising high-molar-mass hyaluronan and ascorbate plus Cu(II) ions was used. Primarily, the effects of replacement of ascorbic acid in this system by D-penicillamine were investigated. Then, D-penicillamine was added into the above degradative system before reaction onset or 1h after the reaction had started. To monitor hyaluronan degradation kinetics, rotational viscometry was applied.


RESULTS
No hyaluronan degradation occurred when ascorbate was replaced by D-penicillamine. The drug addition into the complete degradative system at the reaction onset caused a marked inhibition of hyaluronan degradation. However, the inhibitory effect turned to a pro-oxidative one within appr. 1 h.


CONCLUSIONS
The dual behavior of D-penicillamine on hyaluronan degradation can relate to: (i) the drug completely traps *OH radicals generated from ascorbate plus Cu(II) ions under aerobic conditions; (ii) thiyl radicals generated from D-penicillamine react with D-penicillamine anions resulting in novel radical reactive species, which e.g. by reducing dioxygen molecules can generate further *OH radicals.
Valachova
Katarina
K
Institute of Experimental Pharmacology, Slovak Academy of Sciences, Bratislava, Slovakia.
Hrabarova
Eva
E
Gemeiner
Peter
P
Soltes
Ladislav
L
D000975:Antioxidants / Q000737:chemistry*; D001205:Ascorbic Acid / Q000737:chemistry*; D002240:Carbohydrate Sequence; D003300:Copper / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D006820:Hyaluronic Acid / Q000737:chemistry*; D006861:Hydrogen Peroxide / Q000737:chemistry; D017665:Hydroxyl Radical / Q000737:chemistry; D007700:Kinetics; D008970:Molecular Weight; D016877:Oxidants / Q000737:chemistry; D010396:Penicillamine / Q000737:chemistry*; D014783:Viscosity
D000975:Antioxidants; D005609:Free Radicals; D016877:Oxidants; D017665:Hydroxyl Radical; D003300:Copper; D006820:Hyaluronic Acid; D006861:Hydrogen Peroxide; D010396:Penicillamine; D001205:Ascorbic Acid