title: Synthesis of cynaropicrin-d(4).
abstract: Cynaropicrin is a guaianolide sesquiterpene lactone, which has potent in vitro and in vivo inhibitory activity against Trypanosoma brucei, the protozoan parasite that causes human African trypanosomiasis (HAT; sleeping sickness). Herein, we describe the synthesis of cynaropicrin's deuterated derivative, cynaropicrin-d4, by the replacement of the side chain of natural cynaropicrin. The synthesized cynaropicrin-d4 could be employed as an internal standard for liquid chromatography-mass spectrometry (LC-MS) analysis, in the pharmacokinetic study of cynaropicrin. This could potentially advance the study of this therapeutic lead.
authors.affiliation: Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, Tokyo 102-8554, Japan.
authors.forename: Takuya
authors.initials: T
authors.lastname: Sato
authors.affiliation: Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, Tokyo 102-8554, Japan.
authors.forename: Shihori
authors.initials: S
authors.lastname: Hara
authors.affiliation: Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, Tokyo 102-8554, Japan.
authors.forename: Makiko
authors.initials: M
authors.lastname: Sato
authors.affiliation: Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, Tokyo 102-8554, Japan.
authors.forename: Keita
authors.initials: K
authors.lastname: Ogawa
authors.affiliation: Bacoba AG, Einsiedlerstrasse 25, CH-8820 Wädenswil, Switzerland.
authors.forename: Michael
authors.initials: M
authors.lastname: Adams
authors.affiliation: Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, Tokyo 102-8554, Japan. Electronic address: t-usuki@sophia.ac.jp.
authors.forename: Toyonobu
authors.initials: T
authors.lastname: Usuki
mesh_terms: D003903:Deuterium / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D014344:Trypanocidal Agents / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D007783:Lactones; D012717:Sesquiterpenes; D014344:Trypanocidal Agents; C000611188:cynaropicrin-d; D003903:Deuterium; C075687:cynaropicrin
keywords: Cynaropicrin; Deuterium; Guaianolide; Pharmacokinetic study; Trypanosoma brucei