Biochemical and Biophysical Research Communications, Vol.297, No.5, 1238-1244, 2002
Nitration and chlorination of folic acid by peroxynitrite and hypochlorous acid, and the selective binding of 10-nitro-folate to folate receptor beta
The aim of this work was to characterize folates modified by ONOO- and HOCl and to evaluate the binding capacity of folates modified by ONOO-to folate receptor alpha and beta. For the modification of folate by ONOO-, folic acid was reacted with the combination of PMA activated PMN and PAPA NONOate or chemically synthesized ONOO-. For the modification of folate by HOCl, folic acid was reacted with the combination of MPO and H2O2 or NaOCl The structures of products were determined by H-1-NMR and MALDI-TOF mass. Nitrated folate species were identified as 10-nitro-folate and 12-nitro-folate, and chlorinated folate was identified as 12-chloro-folate. The 10-nitro-folate showed the selective binding to FR-beta, compared to folic acid. (C) 2002 Elsevier Science (USA). All rights reserved.
Keywords:folic acid;peroxynitrite;nitration;hypochlorous acid;chlorination;reactivity indices;frontier theory;binding capacity;folate receptor beta