Binding Mode of Phospholipase A2 with a New Type of Phospholipid Analog Having an Oxazolidinone Ring.

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概要

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• Inhibition of phospholipases A2 (PLA2s) by a new type of monodispersed phospholipid analog, 3-dodecanoyl-4-phosphatidylcholinohydroxymethyl-2-oxazolidinone (oxazolidinone-PC), was investigated by the pH stat assay method using monodispersed 1, 2-dihexanoyl-sn-glycero-3-phosphorylcholine (diC6PC) as the substrate. The PLA2s used were those from bovine pancreas and cobra (Naja naja atra) venom (Group I) and from Japanese mamushi (Agkistrodon halys blomhoffii) venom (Group II). This new-type substrate analog was shown to inhibit competitively both types of venom and bovine pancreatic enzymes by binding to the active site in a similar manner to the carboxamide-type analog 2-dodecanoyl-amino-1-hexanol-phosphocholine (amide-PC). The binding of a stereoisomer, (R) -amide-PC, to N. naja atra (Group I) and A. halys blomhoffii (Group II) PLA2s was facilitated by the binding of Ca2+ to the enzymes. On the other hand, the binding of (R) -oxazolidinone-PC to the N. naja atra (Group I) enzyme was found to be independent of Ca2+ binding, while its binding to the A. halys blomhoffii (Group II) enzyme was markedly facilitated by the binding of Ca2+ to the enzyme. The binding of (R)-amide-PC to N. naja atra PLA2 (Group I) was markedly influenced by the ionization state of the catalytic residue His 48, whereas the binding of (R)-oxazolidinone-PC was found to be practically independent of the ionization state of this residue. The Ca2+ dependency and participation of the catalytic group His 48 in the binding of genuine substrate to both types of PLA2s were found to be very similar to those for the oxazolidinone-PC, but differed greatly from those for the amide-PC, indicating that the binding mode of oxazolidinone-PC is very similar to that of the genuine substrate, but very different from that of the amide-PC.

• 社団法人 日本生化学会の論文

著者

• IWAMA Seiji

  Faculty of Science, Kwansei Gakuin University

• KATSUMURA Shigeo

  Faculty of Engineering, Mie University

• TANI Takeshi

  Department of Biochemistry, Osaka University of Pharmaceutical Sciences

• Ikeda Kiyoshi

  Department Of Biochemistry Osaka University Of Pharmaceutical Sciences

• Hayashi Kyozo

  Department Of Biochemistry Osaka University Of Pharmaceutical Sciences

• Fujii Shinobu

  Department Of Dermatology Osaka Red Cross Hospital

• Samejima Yuji

  Department Of Hyginic Chemistry Faculty Of Pharmacy Hoshi University

• Matsuda Takeshi

  Faculty Of Science Kwansei Gakuin University

• Inoue Seiji

  Department of Applied Electronics, Tokyo University of Science

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