Radiosynthesis and preliminary evaluation of 5-[(123/125)I]iodo-3- (2(S)-azetidinylmethoxy)pyridine: A radioligand for nicotinic acetylcholine receptors

Andrew G. Horti; Andrei O. Koren; Kan Sam Lee; Alexey G. Mukhin; D. Bruce Vaupel; Alane S. Kimes; Morgan Stratton; Edythe D. London

doi:10.1016/S0969-8051(98)00086-9

Radiosynthesis and preliminary evaluation of 5-[(123/125)I]iodo-3- (2(S)-azetidinylmethoxy)pyridine: A radioligand for nicotinic acetylcholine receptors

Andrew G. Horti, Andrei O. Koren, Kan Sam Lee, Alexey G. Mukhin, D. Bruce Vaupel, Alane S. Kimes, Morgan Stratton, Edythe D. London

Research output: Contribution to journal › Article › peer-review

Abstract

The radiochemical syntheses of 5-[¹²⁵I]iodo-3-(2(S)- azetidinylmethoxy)pyridine (5-[¹²⁵I]-iodo-A-85380, [¹²⁵I]1) and 5- [¹²³I]-iodo-A-85380, [¹²³I]1, were accomplished by radioiodination of 5-trimethylstannyl-3-((1-tert-butoxycarbonyl-2(S)- azetidinyl)methoxy)pyridine, 2, followed by acidic deprotection. Average radiochemical yields of [¹²⁵I]1 and [¹²³I]1 were 40-55%; and the average specific radioactivities were 1,700 and 7,000 mCi/μmol, respectively. Binding affinities of [¹²⁵I] 1 and [¹²³I] 1 in vitro (rat brain membranes) were each characterized by a K(d) value of 11 pM. Preliminary in vivo assay and ex vivo autoradiography of mouse brain indicated that [¹²⁵I]1 selectively labels nicotinic acetylcholine receptors (nAChRs) with very high affinity and specificity. These studies suggest that [¹²³I]1 may be useful as a radioligand for single photon emission computed tomography (SPECT) imaging of nAChRs.

Original language	English (US)
Pages (from-to)	175-182
Number of pages	8
Journal	Nuclear Medicine and Biology
Volume	26
Issue number	2
DOIs	https://doi.org/10.1016/S0969-8051(98)00086-9
State	Published - Feb 1999
Externally published	Yes

Keywords

A-85380
Acetylcholine
I
I
Nicotinic receptors
Radioiodination
Radiotracer
Receptor binding
SPECT

ASJC Scopus subject areas

Molecular Medicine
Radiology Nuclear Medicine and imaging
Cancer Research

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title = "Radiosynthesis and preliminary evaluation of 5-[(123/125)I]iodo-3- (2(S)-azetidinylmethoxy)pyridine: A radioligand for nicotinic acetylcholine receptors",

abstract = "The radiochemical syntheses of 5-[125I]iodo-3-(2(S)- azetidinylmethoxy)pyridine (5-[125I]-iodo-A-85380, [125I]1) and 5- [123I]-iodo-A-85380, [123I]1, were accomplished by radioiodination of 5-trimethylstannyl-3-((1-tert-butoxycarbonyl-2(S)- azetidinyl)methoxy)pyridine, 2, followed by acidic deprotection. Average radiochemical yields of [125I]1 and [123I]1 were 40-55%; and the average specific radioactivities were 1,700 and 7,000 mCi/μmol, respectively. Binding affinities of [125I] 1 and [123I] 1 in vitro (rat brain membranes) were each characterized by a K(d) value of 11 pM. Preliminary in vivo assay and ex vivo autoradiography of mouse brain indicated that [125I]1 selectively labels nicotinic acetylcholine receptors (nAChRs) with very high affinity and specificity. These studies suggest that [123I]1 may be useful as a radioligand for single photon emission computed tomography (SPECT) imaging of nAChRs.",

keywords = "A-85380, Acetylcholine, I, I, Nicotinic receptors, Radioiodination, Radiotracer, Receptor binding, SPECT",

author = "Horti, {Andrew G.} and Koren, {Andrei O.} and Lee, {Kan Sam} and Mukhin, {Alexey G.} and Vaupel, {D. Bruce} and Kimes, {Alane S.} and Morgan Stratton and London, {Edythe D.}",

year = "1999",

month = feb,

doi = "10.1016/S0969-8051(98)00086-9",

language = "English (US)",

volume = "26",

pages = "175--182",

journal = "International journal of radiation applications and instrumentation. Part B, Nuclear medicine and biology",

issn = "0969-8051",

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number = "2",

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T1 - Radiosynthesis and preliminary evaluation of 5-[(123/125)I]iodo-3- (2(S)-azetidinylmethoxy)pyridine

T2 - A radioligand for nicotinic acetylcholine receptors

AU - Horti, Andrew G.

AU - Koren, Andrei O.

AU - Lee, Kan Sam

AU - Mukhin, Alexey G.

AU - Vaupel, D. Bruce

AU - Kimes, Alane S.

AU - Stratton, Morgan

AU - London, Edythe D.

PY - 1999/2

Y1 - 1999/2

N2 - The radiochemical syntheses of 5-[125I]iodo-3-(2(S)- azetidinylmethoxy)pyridine (5-[125I]-iodo-A-85380, [125I]1) and 5- [123I]-iodo-A-85380, [123I]1, were accomplished by radioiodination of 5-trimethylstannyl-3-((1-tert-butoxycarbonyl-2(S)- azetidinyl)methoxy)pyridine, 2, followed by acidic deprotection. Average radiochemical yields of [125I]1 and [123I]1 were 40-55%; and the average specific radioactivities were 1,700 and 7,000 mCi/μmol, respectively. Binding affinities of [125I] 1 and [123I] 1 in vitro (rat brain membranes) were each characterized by a K(d) value of 11 pM. Preliminary in vivo assay and ex vivo autoradiography of mouse brain indicated that [125I]1 selectively labels nicotinic acetylcholine receptors (nAChRs) with very high affinity and specificity. These studies suggest that [123I]1 may be useful as a radioligand for single photon emission computed tomography (SPECT) imaging of nAChRs.

AB - The radiochemical syntheses of 5-[125I]iodo-3-(2(S)- azetidinylmethoxy)pyridine (5-[125I]-iodo-A-85380, [125I]1) and 5- [123I]-iodo-A-85380, [123I]1, were accomplished by radioiodination of 5-trimethylstannyl-3-((1-tert-butoxycarbonyl-2(S)- azetidinyl)methoxy)pyridine, 2, followed by acidic deprotection. Average radiochemical yields of [125I]1 and [123I]1 were 40-55%; and the average specific radioactivities were 1,700 and 7,000 mCi/μmol, respectively. Binding affinities of [125I] 1 and [123I] 1 in vitro (rat brain membranes) were each characterized by a K(d) value of 11 pM. Preliminary in vivo assay and ex vivo autoradiography of mouse brain indicated that [125I]1 selectively labels nicotinic acetylcholine receptors (nAChRs) with very high affinity and specificity. These studies suggest that [123I]1 may be useful as a radioligand for single photon emission computed tomography (SPECT) imaging of nAChRs.

KW - A-85380

KW - Acetylcholine

KW - I

KW - Nicotinic receptors

KW - Radioiodination

KW - Radiotracer

KW - Receptor binding

KW - SPECT

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JF - International journal of radiation applications and instrumentation. Part B, Nuclear medicine and biology

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IS - 2

ER -

Radiosynthesis and preliminary evaluation of 5-[(123/125)I]iodo-3- (2(S)-azetidinylmethoxy)pyridine: A radioligand for nicotinic acetylcholine receptors

Abstract

Keywords

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