Radiolabeling of ginkgolide B with <sup>18</sup>F

Suehiro, Makiko; Simpson, Norman R.; Heertum, Ronald Van

doi:10.1002/jlcr.836

Cited by 7 publications

(3 citation statements)

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“…The radiosyntheses of the 18 F-labeled GB, 7-18 FGB, and 3 HGB are described elsewhere [11], [12]. The animal experiments were performed according to the animal protocol approved by the Columbia University Medical Center Institutional Animal Care and Use Committee.…”

Section: Methodsmentioning

confidence: 99%

“…However, their in vivo behavior in the living body has not been reported. Visualization of their in vivo dynamic distribution by means of an imaging technique such as positron emission tomography (PET) with an analogue of ginkgolides labeled with a positron emitter such as 11 C or 18 F provides unique information which sheds light on the role of ginkgolides in both physiological and pathological conditions. We report here the in vivo behavior of 18 F-labeled ginkgolide B in the rodent visualized by the PET technique for small animals, microPET.…”

Section: Introductionmentioning

confidence: 99%

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In vivoBiodistribution of Ginkgolide B, a Constituent ofGinkgo biloba, Visualized by MicroPET

Suehiro¹,

Simpson²,

Underwood³

et al. 2005

Planta med

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The in vivo dynamic behavior of ginkgolide B (GB), a terpene lactone constituent of the Ginkgo biloba extracts, in the living animal was visualized by positron emission tomographic (PET) imaging using a GB analogue labeled with the positron emitter (18)F. The in vivo imaging studies, combined with ex vivo dissection experiments, reveal that GB exists in 2 forms in the body: the original GB with its lactone rings closed and a second form with one of the rings open. The original GB in plasma is taken up rapidly by various organs including the liver, the intestine and possibly the stomach. Consequently, in plasma, the proportion of the ionized form of GB increases dramatically with time. Thereafter the ratio between the 2 forms appears to shift slowly towards equilibrium. The results suggest that more attention needs to be focused on in vivo dynamics between the 2 forms of GB.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

In vivoBiodistribution of Ginkgolide B, a Constituent ofGinkgo biloba, Visualized by MicroPET

Suehiro¹,

Simpson²,

Underwood³

et al. 2005

Planta med

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“…In an attempt to search for novel targets for ginkgolides, radiolabeled versions of ginkgolides have been prepared including [ 3 H]- and [ 18 F]-labeled GB. , Although biodistribution studies in rats using [ 3 H]-GB showed that GB ( 2 ) entered the brain, the amounts detected in the brain by positron emission tomography (PET) using [ 18 F]-GB was too low to be unambiguously determined . Instead, the first indication of a direct interaction between ginkgolides and important targets in the brain was discovered, when ginkgolides were shown to be potent and highly selective antagonists of the inhibitory strychnine-sensitive glycine receptor (GlyR). − The GlyRs are ligand-gated ion channels found primarily in the spinal cord and brain stem, but also in higher brain regions such as the hippocampus and developing cortex.…”

Section: Introductionmentioning

confidence: 99%

Probing the Pharmacophore of Ginkgolides as Glycine Receptor Antagonists

et al. 2007

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Ginkgolides are antagonists of the inhibitory ligand-gated ion channels for the neurotransmitters glycine and gamma-aminobutyric acid (GABA). In this study the ginkgolide structure was modified in order to investigate the minimum structural requirements for glycine receptor antagonism. The five native ginkgolides and a series of 29 ginkgolide derivatives were characterized at the three glycine receptor subtypes alpha1, alpha1beta, and alpha2, which revealed that only minor changes in the ginkgolide skeleton were allowed for maintaining glycine receptor antagonism. A pharmacophore model was generated and applied in a virtual screening of a compound database (300000 compounds), resulting in the identification of 31 hits. Twenty-seven of these hits were screened for biological activity, but none displayed antagonist activity at the glycine receptors. This strongly suggests the importance of other pharmacophore components in the binding of ginkgolides to glycine receptors, and we propose that the structural rigidity of the ginkgolide molecule may be crucial for its glycine receptor activity.

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Preparation of 9α‐Fluorinated Sesquiterpenic Drimanes and Evaluation of Their Antifeedant Activities

Abad¹,

Agulló²,

Cuñat³

et al. 2010

Eur J Org Chem

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The preparation of 9α‐fluoro analogues of both natural and unnatural drimane‐type sesquiterpenes is described. Their synthesis began with the initial preparation of methyl 8‐keto‐12‐nordriman‐11‐oate from β‐ionone and entailed the electrophilic fluorination of C‐9 for the stereoselective introduction of the fluorine atom. The drimane skeleton was completed from the intermediate 9α‐fluoro‐8‐keto‐12‐nordrimane system by means of different reactions at the C‐8 ketone carbonyl group, essentially Wittig methylenation, cyanohydrin formation or palladium‐catalysed carbonylation of the corresponding enol triflate. Further manipulation of the functionalization derived from these key reactions allowed the preparation, among others, of 9α‐fluorodrimanes, which are structurally and functionally related to albicanic acid, drimenin and olepupuane. Also described are the reactivities of some of the fluorine‐containing systems prepared and a comparative study of the antifeedant activities of a selection of 9α‐fluorodrimanes and the corresponding hydrogen analogues against several insect species with different feeding ecologies (Spodoptera littoralis, Myzus persicae and Rhopalosiphum padi), which revealed a significant increase in the antifeedant activities of some of the fluorinated drimane analogues.

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Radiolabeling of ginkgolide B with ¹⁸F

Abstract: SummaryGinkgolide B, a terpene trilactone constituent of Gingko biloba extracts and an antagonist for the platelet activating factor (PAF) receptor, was radiolabeled with the positron emitter 18 F for visualizing its in vivo behavior using positron emission tomography (PET

Cited by 7 publications

References 15 publications

In vivoBiodistribution of Ginkgolide B, a Constituent ofGinkgo biloba, Visualized by MicroPET

In vivoBiodistribution of Ginkgolide B, a Constituent ofGinkgo biloba, Visualized by MicroPET

Probing the Pharmacophore of Ginkgolides as Glycine Receptor Antagonists

Preparation of 9α‐Fluorinated Sesquiterpenic Drimanes and Evaluation of Their Antifeedant Activities

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Radiolabeling of ginkgolide B with 18F

Abstract: SummaryGinkgolide B, a terpene trilactone constituent of Gingko biloba extracts and an antagonist for the platelet activating factor (PAF) receptor, was radiolabeled with the positron emitter 18 F for visualizing its in vivo behavior using positron emission tomography (PET

Cited by 7 publications

References 15 publications

In vivoBiodistribution of Ginkgolide B, a Constituent ofGinkgo biloba, Visualized by MicroPET

In vivoBiodistribution of Ginkgolide B, a Constituent ofGinkgo biloba, Visualized by MicroPET

Probing the Pharmacophore of Ginkgolides as Glycine Receptor Antagonists

Preparation of 9α‐Fluorinated Sesquiterpenic Drimanes and Evaluation of Their Antifeedant Activities

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Radiolabeling of ginkgolide B with ¹⁸F