Antimalarial activity of 6-(1,2,6,7-tetraoxaspiro[7.11]nonadec-4-yl)hexan-1-ol (N-251) and its carboxylic acid derivatives

Akira Sato, Satoru Kawai, Akiko Hiramoto, Masayuki Morita, Natsuki Tanigawa, Yukari Nakase, Yuka Komichi, Masahiro Matsumoto, Osamu Hiraoka, Kazuyuki Hiramoto, Hidekazu Tokuhara, Araki Masuyama, Masatomo Nojima, Kazutaka Higaki, Hikoya Hayatsu, Yusuke Wataya, Hye-Sook Kim

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Malaria is one of the world's deadliest diseases and is becoming an increasingly serious problem as malaria parasites develop resistance to most of the antimalarial drugs used today. We previously reported the in vitro and in vivo antimalarial potencies of 1,2,6,7-tetraoxaspiro[7.11]nonadecane (N-89) and 6-(1,2,6,7-tetraoxaspiro[7.11]nonadec-4-yl)hexan-1-ol (N-251) against Plasmodium falciparum and Plasmodium berghei parasites. To improve water-solubility for synthetic peroxides, a variety of cyclic peroxides having carboxyl functionality was prepared based on the antimalarial candidate, N-251, and their antimalarial activities were determined. The reactions of N-89 and its derivatives with Fe(II) demonstrated a highly efficient formation of the corresponding carbon radical which may be suspected as a key for the antiparasitic activity.

Original languageEnglish
Pages (from-to)488-492
Number of pages5
JournalParasitology International
Volume60
Issue number4
DOIs
Publication statusPublished - Dec 2011

Fingerprint

Antimalarials
Carboxylic Acids
Peroxides
Malaria
Parasites
Antiparasitic Agents
Plasmodium berghei
Plasmodium falciparum
Solubility
Carbon
6-(1,2,6,7-tetraoxaspiro(7.11)nonadec-4-yl)hexan-1-ol
Water

Keywords

  • 6-(1,2,6,7-tetraoxaspiro[7.11]nonadec-4-yl)hexan-1-ol
  • Antimalarial activity
  • Carbon radical
  • N-251
  • Plasmodium berghei
  • Plasmodium falciparum

ASJC Scopus subject areas

  • Parasitology
  • Infectious Diseases

Cite this

Antimalarial activity of 6-(1,2,6,7-tetraoxaspiro[7.11]nonadec-4-yl)hexan-1-ol (N-251) and its carboxylic acid derivatives. / Sato, Akira; Kawai, Satoru; Hiramoto, Akiko; Morita, Masayuki; Tanigawa, Natsuki; Nakase, Yukari; Komichi, Yuka; Matsumoto, Masahiro; Hiraoka, Osamu; Hiramoto, Kazuyuki; Tokuhara, Hidekazu; Masuyama, Araki; Nojima, Masatomo; Higaki, Kazutaka; Hayatsu, Hikoya; Wataya, Yusuke; Kim, Hye-Sook.

In: Parasitology International, Vol. 60, No. 4, 12.2011, p. 488-492.

Research output: Contribution to journalArticle

Sato, A, Kawai, S, Hiramoto, A, Morita, M, Tanigawa, N, Nakase, Y, Komichi, Y, Matsumoto, M, Hiraoka, O, Hiramoto, K, Tokuhara, H, Masuyama, A, Nojima, M, Higaki, K, Hayatsu, H, Wataya, Y & Kim, H-S 2011, 'Antimalarial activity of 6-(1,2,6,7-tetraoxaspiro[7.11]nonadec-4-yl)hexan-1-ol (N-251) and its carboxylic acid derivatives', Parasitology International, vol. 60, no. 4, pp. 488-492. https://doi.org/10.1016/j.parint.2011.08.017
Sato, Akira ; Kawai, Satoru ; Hiramoto, Akiko ; Morita, Masayuki ; Tanigawa, Natsuki ; Nakase, Yukari ; Komichi, Yuka ; Matsumoto, Masahiro ; Hiraoka, Osamu ; Hiramoto, Kazuyuki ; Tokuhara, Hidekazu ; Masuyama, Araki ; Nojima, Masatomo ; Higaki, Kazutaka ; Hayatsu, Hikoya ; Wataya, Yusuke ; Kim, Hye-Sook. / Antimalarial activity of 6-(1,2,6,7-tetraoxaspiro[7.11]nonadec-4-yl)hexan-1-ol (N-251) and its carboxylic acid derivatives. In: Parasitology International. 2011 ; Vol. 60, No. 4. pp. 488-492.
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