Syntheses and in vitro evaluation of decalinvesamicol analogues as potential imaging probes for vesicular acetylcholine transporter (VAChT)

Kozaka, Takashi; Uno, Izumi; Kitamura, Yoshihisa; Miwa, Daisuke; Ogawa, Kenji; Shiba, Kazuhiro

doi:10.1016/j.bmc.2012.06.040

Cited by 14 publications

(26 citation statements)

References 26 publications

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“…The intracerebral biodistribution pattern of [ 77 Br]OBDV (Table I) revealed maximum accumulation of radioactivity (>0.6 % ID/g) at 2 min postinjection in the cerebral cortex, striatum, cerebellum, and the rest and confirmed the rapid penetration of Br]OBDV was observed in the striatum, which corresponded to the known distribution of VAChT density as the highest level was found in the striatum (Efange et al, 1995Frey et al, 1998 (Kozaka et al, 2014). The initial blood uptake of [ 77 Br]OBDV was low (0.14 6 0.01% ID/g).…”

Section: Discussionsupporting

confidence: 80%

“…Previously reported in vitro evaluation of OBDV revealed its high affinity and selectivity for VAChT (Kozaka et al, 2012). Hence, OBDV, radiolabeled with a suitable positron emitter, was expected to be a potential VAChT PET ligand.…”

Section: Discussionmentioning

confidence: 98%

“…According to our previously published method (Kozaka et al, 2012), 4-(2-bromophenyl) piperidine, key intermediate for the synthesis of OBDV was derived from ortho-bromobenzaldehyde by four-step reactions and the coupling reaction of 4-(2-bromophenyl) piperidine with trans-decalin-2,3-oxide furnished OBDV in 57% yield (Kozaka et al, 2012). The bromo substituent of OBDV was replaced by a trimethylstannyl group by the reaction of Pd(PPh 3 ) 4 and hexamethylditin to obtain the corresponding precursor, o-trimethylstannyltrans-decalinvesamicol (OTDV), for the radiosynthesis of [ 77 Br]OBDV, with an yield of 65% (Kozaka et al, 2012).…”

Section: Materials and Methods Synthesis Of Obdv And Otdvmentioning

confidence: 99%

“…The bromo substituent of OBDV was replaced by a trimethylstannyl group by the reaction of Pd(PPh 3 ) 4 and hexamethylditin to obtain the corresponding precursor, o-trimethylstannyltrans-decalinvesamicol (OTDV), for the radiosynthesis of [ 77 Br]OBDV, with an yield of 65% (Kozaka et al, 2012). DV was prepared according to Roger's protocol (Rogers et al, 1989).…”

Section: Materials and Methods Synthesis Of Obdv And Otdvmentioning

confidence: 99%

“…On the basis of the observations of DV and (-)-oIV, we synthesized o-bromo-trans-decalinvesamicol (OBDV) and o-iodo-trans-decalinvesamicol (OIDV) (Fig. 1), two new decalinvesamicol (DV) analogues with halogen (-Br, -I) at the ortho-position of the 4-phenylpiperidine moiety (Kozaka et al, 2012). We previously reported the high potential of radioiodinated OIDV as a VAChT SPECT ligand for the early diagnosis of AD (Kozaka et al, 2012(Kozaka et al, , 2014.…”

Section: Introductionmentioning

confidence: 99%

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The potential ofo-bromo-trans-decalinvesamicol as a new PET ligand for vesicular acetylcholine transporter imaging

Azim

Kozaka

Uno

et al. 2014

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We investigated the characteristics of the regional rat brain distribution of radio-brominated o-bromo-decalinvesamicol (OBDV) in vivo to evaluate its potential as a PET ligand for vesicular acetylcholine transporter (VAChT). In in vivo biodistribution study, the specific brain regional accumulation of [(77) Br]OBDV was revealed 30 min after intravenous injection. The specific brain regional accumulation of [(77) Br]OBDV was significantly inhibited by co-injection of (+/-)-vesamicol. In contrast, no significant inhibition of the uptake of [(77) Br]OBDV in all brain regions was observed with co-injection of (+)-pentazocine (selective σ-1 receptor agonist) and (+)-3-(3-hydroxyphenyl)-N-propylpiperidine, [(+)-3-PPP] (σ-1 and σ-2 receptor agonist) with [(77) Br]OBDV. [(77) Br]OBDV accumulation in VAChT-rich brain regions was observed in ex vivo autoradiography. These results showed that [(77) Br]OBDV selectively bound to VAChT with high affinity in rat brain in vivo. Hence, OVBDV radiolabelled with more suitable (76) Br was suggested to be a potent VAChT ligand for PET.

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Section: Discussionsupporting

confidence: 80%

Section: Discussionmentioning

confidence: 98%

Section: Materials and Methods Synthesis Of Obdv And Otdvmentioning

confidence: 99%

Section: Materials and Methods Synthesis Of Obdv And Otdvmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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The potential ofo-bromo-trans-decalinvesamicol as a new PET ligand for vesicular acetylcholine transporter imaging

Azim

Kozaka

Uno

et al. 2014

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Investigations into the Au^I and Pt^II Coordination Chemistry of Bidentate “cis‐Spanning” Ligands

Kaufmann,

Föhrenbacher,

Krummer

et al. 2023

Eur J Inorg Chem

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The novel bidentate PP and PN ligands o‐(Ph2P)−C6H4−C≡C−PPh2 (LPP) and o‐(Ph2P)−C6H4−4−(C5H9N−Me) (LPN), respectively, have been designed as long‐range “cis‐spanning“ ligands for the stabilization of heterodinuclear complexes containing two metal atoms in close proximity. The synthesis of heterodinuclear, formal AuIPtII complexes with the ligand LPP is straightforward. In the course of a one‐pot reaction, a surprisingly high selectivity for the coordination of AuCl and Pt(CNC) (CNC=2,6‐diphenylpyridine‐o,o’‐diate) to the phenyl‐bound and the alkyne‐bound PPh2 sites of LPP is observed, respectively. Chloride abstraction from the resulting heterodinuclear complex [(ClAu)(o‐Ph2P)−C6H4−C≡C−PPh2(Pt{CNC})] with Ag[SbF6] causes metal–metal bond formation and the generation of the cationic complex [LPPAuPt(CNC)][SbF6]. The high site selectivity for the coordination of the two metals to LPP was investigated by stoichiometric reactions of the ligand with one equivalent of the corresponding precursors. While analogous complexation experiments with LPN have not been successful, the synthesis of the heterodinuclear complex [(ClAu)(o‐Ph2P)−C6H4−4‐(C5H9N−Me)(PtCl2{dmso})] and of [LPN(AuCl)2] confirm the ability of LPN to serve as a ditopic ligand. In this context, it is noteworthy that [LPN(AuCl)2] constitutes the first amine–AuCl complex featuring a tertiary amine.

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Regional brain imaging of vesicular acetylcholine transporter using o‐[¹²⁵I]iodo‐trans‐decalinvesamicol as a new potential imaging probe

Kozaka

Uno

Kitamura

et al. 2013

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In this study, the regional rat brain distribution of radioiodinated o-iodo-trans-decalinvesamicol ([(125) I]OIDV) was determined in vivo to evaluate its potential as a single-photon emission computed tomography (SPECT) imaging probe for vesicular acetylcholine transporter (VAChT). Following intravenous injection, [(125) I]OIDV passed freely across the blood-brain barrier and accumulated in rat brain. The accumulation of [(125) I]OIDV in rat brain was significantly reduced by coadministration of (+/-)-vesamicol (0.125 µmol). In contrast, the coadministration of σ-receptor ligands, such as (+)-pentazocine (0.125 µmol) as a σ-1 receptor ligand and (+)-3-(3-hydroxyphenyl)-N-propylpiperidine (0.125 µmol) as a σ-1 and σ-2 receptor ligands, barely affected the accumulation of [(125) I]OIDV in rat brain. These findings in vivo were corroborated by autoradiographic analysis ex vivo. The authors found that the tracer binds with pharmacological selectivity to VAChT in rat brain and predicted that it may likewise serve in translational SPECT imaging studies of this marker in the integrity of cholinergic innervations.

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Syntheses and in vitro evaluation of decalinvesamicol analogues as potential imaging probes for vesicular acetylcholine transporter (VAChT)

Cited by 14 publications

References 26 publications

The potential ofo-bromo-trans-decalinvesamicol as a new PET ligand for vesicular acetylcholine transporter imaging

The potential ofo-bromo-trans-decalinvesamicol as a new PET ligand for vesicular acetylcholine transporter imaging

Investigations into the Au^I and Pt^II Coordination Chemistry of Bidentate “cis‐Spanning” Ligands

Regional brain imaging of vesicular acetylcholine transporter using o‐[¹²⁵I]iodo‐trans‐decalinvesamicol as a new potential imaging probe

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Syntheses and in vitro evaluation of decalinvesamicol analogues as potential imaging probes for vesicular acetylcholine transporter (VAChT)

Cited by 14 publications

References 26 publications

The potential ofo-bromo-trans-decalinvesamicol as a new PET ligand for vesicular acetylcholine transporter imaging

The potential ofo-bromo-trans-decalinvesamicol as a new PET ligand for vesicular acetylcholine transporter imaging

Investigations into the AuI and PtII Coordination Chemistry of Bidentate “cis‐Spanning” Ligands

Regional brain imaging of vesicular acetylcholine transporter using o‐[125I]iodo‐trans‐decalinvesamicol as a new potential imaging probe

Contact Info

Product

Resources

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Investigations into the Au^I and Pt^II Coordination Chemistry of Bidentate “cis‐Spanning” Ligands

Regional brain imaging of vesicular acetylcholine transporter using o‐[¹²⁵I]iodo‐trans‐decalinvesamicol as a new potential imaging probe