Singlet oxygen (1deltag) production by pterin derivatives in aqueous solutions

Six compounds of the pterin family (pterin, 6-carboxypterin, 6-formylpterin, folic acid, biopterin and neopterin) have been investigated for their efficiencies of singlet oxygen (O2(1deltag)) production and quenching in aqueous solutions. The quantum yields of 1O2 production (phidelta) have been determined by measurements of the 1O2 luminescence in the near-infrared (1270 nm) upon continuous excitation of the sensitizer. Under our experimental conditions, all studied compounds (except folic acid) are relatively efficient 1O2 sensitizers with phidelta values of up to 0.47. Results show that the nature of the substituent at position 6 on the pterin moiety, as well as the pH, affect considerably the capacity of pterins to produce 1O2. All compounds investigated are efficient 1O2 quenchers: the rate constant of 1O2 total quenching (kt) by folic acid (3.0(+/- 0.3) x 10(7) M(-1) s(-1)) is one order of magnitude larger than those for the other pterin derivatives investigated (1.4(+/- 0.1) x 10(6) M(-1) s(-1) to 2.9(+/- 0.3) x 10(6) M(-1) s(-1)).