Synthesis and in vivo evaluation of [11C]MPTQ: A potential PET tracer for alpha2A-adrenergic receptors

Jaya Prabhakaran; Vattoly J. Majo; Matthew S. Milak; Pratap Mali; Lyudmila Savenkova; J. John Mann; Ramin V. Parsey; J. S.Dileep Kumar

doi:10.1016/j.bmcl.2010.04.099

Synthesis and in vivo evaluation of [¹¹C]MPTQ: A potential PET tracer for alpha2A-adrenergic receptors

Jaya Prabhakaran
, Vattoly J. Majo
, Matthew S. Milak
, Pratap Mali
, Lyudmila Savenkova
, J. John Mann
, Ramin V. Parsey
, J. S.Dileep Kumar

Psychiatry

Columbia University

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

11 Scopus citations

Abstract

Radiosynthesis and in vivo evaluation of [N-methyl-¹¹C] 5-methyl-3-[4-(3-phenylallyl)-piperazin-1-ylmethyl]-3,3a,4,5- tetrahydroisoxazolo[4,3-c]quinoline (1), a potential PET tracer for alpha2-adrenergic receptors is described. Syntheses of nonradioactive standard 1 and corresponding desmethyl precursor 2 were achieved from 2-aminobenzaldehyde in 40% and 65% yields, respectively. Methylation using [¹¹C]CH ₃I in presence of aqueous potassium hydroxide in DMSO afforded [ ¹¹C]1 in 25% yield (EOS) with >99% chemical and radiochemical purities with a specific activity ranged from 3-4 Ci/μmol (n = 6). The total synthesis time was 30 min from EOB. PET studies in anesthetized baboon show that [¹¹C]1 penetrates BBB and accumulates in alpha2A-AR enriched brain areas.

Original language	English
Pages (from-to)	3654-3657
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	20
Issue number	12
DOIs	https://doi.org/10.1016/j.bmcl.2010.04.099
State	Published - 2010

Keywords

Alpha2-AR
Baboon
Biological imaging
Positron emission tomography
Radiotracer

Access to Document

10.1016/j.bmcl.2010.04.099

Cite this

@article{5ec7d90ae62e476a9da853528d63dcf2,

title = "Synthesis and in vivo evaluation of [11C]MPTQ: A potential PET tracer for alpha2A-adrenergic receptors",

abstract = "Radiosynthesis and in vivo evaluation of [N-methyl-11C] 5-methyl-3-[4-(3-phenylallyl)-piperazin-1-ylmethyl]-3,3a,4,5- tetrahydroisoxazolo[4,3-c]quinoline (1), a potential PET tracer for alpha2-adrenergic receptors is described. Syntheses of nonradioactive standard 1 and corresponding desmethyl precursor 2 were achieved from 2-aminobenzaldehyde in 40\% and 65\% yields, respectively. Methylation using [11C]CH 3I in presence of aqueous potassium hydroxide in DMSO afforded [ 11C]1 in 25\% yield (EOS) with >99\% chemical and radiochemical purities with a specific activity ranged from 3-4 Ci/μmol (n = 6). The total synthesis time was 30 min from EOB. PET studies in anesthetized baboon show that [11C]1 penetrates BBB and accumulates in alpha2A-AR enriched brain areas.",

keywords = "Alpha2-AR, Baboon, Biological imaging, Positron emission tomography, Radiotracer",

author = "Jaya Prabhakaran and Majo, \{Vattoly J.\} and Milak, \{Matthew S.\} and Pratap Mali and Lyudmila Savenkova and Mann, \{J. John\} and Parsey, \{Ramin V.\} and Kumar, \{J. S.Dileep\}",

year = "2010",

doi = "10.1016/j.bmcl.2010.04.099",

language = "English",

volume = "20",

pages = "3654--3657",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

number = "12",

}

TY - JOUR

T1 - Synthesis and in vivo evaluation of [11C]MPTQ

T2 - A potential PET tracer for alpha2A-adrenergic receptors

AU - Prabhakaran, Jaya

AU - Majo, Vattoly J.

AU - Milak, Matthew S.

AU - Mali, Pratap

AU - Savenkova, Lyudmila

AU - Mann, J. John

AU - Parsey, Ramin V.

AU - Kumar, J. S.Dileep

PY - 2010

Y1 - 2010

N2 - Radiosynthesis and in vivo evaluation of [N-methyl-11C] 5-methyl-3-[4-(3-phenylallyl)-piperazin-1-ylmethyl]-3,3a,4,5- tetrahydroisoxazolo[4,3-c]quinoline (1), a potential PET tracer for alpha2-adrenergic receptors is described. Syntheses of nonradioactive standard 1 and corresponding desmethyl precursor 2 were achieved from 2-aminobenzaldehyde in 40% and 65% yields, respectively. Methylation using [11C]CH 3I in presence of aqueous potassium hydroxide in DMSO afforded [ 11C]1 in 25% yield (EOS) with >99% chemical and radiochemical purities with a specific activity ranged from 3-4 Ci/μmol (n = 6). The total synthesis time was 30 min from EOB. PET studies in anesthetized baboon show that [11C]1 penetrates BBB and accumulates in alpha2A-AR enriched brain areas.

AB - Radiosynthesis and in vivo evaluation of [N-methyl-11C] 5-methyl-3-[4-(3-phenylallyl)-piperazin-1-ylmethyl]-3,3a,4,5- tetrahydroisoxazolo[4,3-c]quinoline (1), a potential PET tracer for alpha2-adrenergic receptors is described. Syntheses of nonradioactive standard 1 and corresponding desmethyl precursor 2 were achieved from 2-aminobenzaldehyde in 40% and 65% yields, respectively. Methylation using [11C]CH 3I in presence of aqueous potassium hydroxide in DMSO afforded [ 11C]1 in 25% yield (EOS) with >99% chemical and radiochemical purities with a specific activity ranged from 3-4 Ci/μmol (n = 6). The total synthesis time was 30 min from EOB. PET studies in anesthetized baboon show that [11C]1 penetrates BBB and accumulates in alpha2A-AR enriched brain areas.

KW - Alpha2-AR

KW - Baboon

KW - Biological imaging

KW - Positron emission tomography

KW - Radiotracer

UR - https://www.scopus.com/pages/publications/77954214162

U2 - 10.1016/j.bmcl.2010.04.099

DO - 10.1016/j.bmcl.2010.04.099

M3 - Article

C2 - 20529687

AN - SCOPUS:77954214162

SN - 0960-894X

VL - 20

SP - 3654

EP - 3657

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 12

ER -

Synthesis and in vivo evaluation of [¹¹C]MPTQ: A potential PET tracer for alpha2A-adrenergic receptors

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this