5,5-dimethyl-1-pyrroline-N-oxide alone enhances the spontaneous superoxide generation by primaquine

L. Prónai, Kohji Ichimori, Yoshinori Saigusa, Hiroe Nakazawa

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Primaquine (PQ), a well-known antimalarial drug, has been reported to generate superoxide (O2 -) in the presence of reducing agents such as NADPH. In the present study, chemiluminescence was detected by adding only PQ to aqueous 2-methyl-6-[p-methoxyphenyl]-3,7-dihydroimidazo-[1,2-α]pyrazin-3-one (MCLA), which is a specific chemiluminescent probe for O2 -, and was quenched by superoxide dismutase (SOD), indicating that PQ alone can generate O2 - in aerobic conditions. Furthermore, 5,5-dimethyl-1-pyrroline-N-oxide (DMPO) enhanced the O2 - generation by PQ. Superoxide spin adduct, DMPO-OOH, was also detected by ESR both in aqueous solutions and in dimethyl sulfoxide with DMPO. The level of O2 - generation showed a linear correlation with the DMPO concentration, and SOD competitively inhibited the DMPO-OOH formation. The results suggested that in aerobic conditions PQ is autoxidized to 5-hydroxy-PQ, which generates O2 -, and DMPO accelerates the autoxidation process by trapping O2 -. DMPO or M4PO alone enhances the spontaneous O2 - generation by PQ, therefore cautious evaluation is necessary in all studies using the ESR/spin trapping technique to elucidate the mechanism of PQ-related radical generation.

Original languageEnglish
Pages (from-to)276-281
Number of pages6
JournalArchives of Biochemistry and Biophysics
Volume288
Issue number1
DOIs
Publication statusPublished - 1991

Fingerprint

Primaquine
Superoxides
Oxides
Superoxide Dismutase
Paramagnetic resonance
Spin Trapping
Chemiluminescence
5,5-dimethyl-1-pyrroline-1-oxide
Reducing Agents
Antimalarials
Dimethyl Sulfoxide
Luminescence
NADP
pyrroline

ASJC Scopus subject areas

  • Biochemistry
  • Biophysics
  • Molecular Biology

Cite this

5,5-dimethyl-1-pyrroline-N-oxide alone enhances the spontaneous superoxide generation by primaquine. / Prónai, L.; Ichimori, Kohji; Saigusa, Yoshinori; Nakazawa, Hiroe.

In: Archives of Biochemistry and Biophysics, Vol. 288, No. 1, 1991, p. 276-281.

Research output: Contribution to journalArticle

Prónai, L. ; Ichimori, Kohji ; Saigusa, Yoshinori ; Nakazawa, Hiroe. / 5,5-dimethyl-1-pyrroline-N-oxide alone enhances the spontaneous superoxide generation by primaquine. In: Archives of Biochemistry and Biophysics. 1991 ; Vol. 288, No. 1. pp. 276-281.
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