Interaction of N1-substituted adenines with 1-methyladenine receptors of starfish oocytes in induction of maturation

Masatoshi Mita, Michiyasu Yoshikuni, Yoshitaka Nagahama, Minako Maekawa, Miho Saito, Mineo Saneyoshi

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3 Citations (Scopus)


Starfish oocytes are arrested naturally in the late G2 phase of the first meiotic division. In response to the natural maturation-inducing hormone, 1-methyladenine (1-MA), oocytes undergo reinitiation of meiosis with germinal vesicle breakdown. We tested 10 newly synthesized N1-substituted adenines that are 1-MA analogues to analyze the interaction between 1-MA and its stereo-specific receptors on the oocyte plasma membranes of the starfish Asterina pectinifera. Among these analogues, 1-(β-naphthylmethyl)adenine, 1-aminoadenine and 1-(p-nitrobenzyl)adenine played agonistic roles in the induction of oocyte maturation. 1-(o-Nitrobenzyl)adenine, 1-(m-nitrobenzyl)adenine, 1-phenethyladenine and 1-(p-nitrophenethyl)adenine had antagonist effects on 1-MA-induced oocyte maturation. These agonists and antagonists behaved competitively in the binding of [3H]1-MA to receptors in oocyte cortices. In contrast, 1-(α-naphthylmethyl)adenine, 1-(2,4-dinitrobenzyl)adenine and 1-(p-methoxybenzyl)adenine had no effects on oocyte maturation. Our results suggest that regional-specific sterical structures at the N1-site of adenine are important in the interaction between 1-MA and its receptors in oocytes. In addition, a negative charge at the N1-site of adenine is required for binding with the receptors.

Original languageEnglish
Pages (from-to)427-434
Number of pages8
JournalComparative Biochemistry and Physiology - B Biochemistry and Molecular Biology
Issue number3
Publication statusPublished - 2001
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physiology
  • Molecular Biology


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