Synthesis of [18F] 4-amino-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide (IDO5L): a novel potential PET probe for imaging of IDO1 expression
Publication type: Journal Article
Publication date: 2015-02-18
scimago Q3
wos Q4
SJR: 0.271
CiteScore: 2.0
Impact factor: 0.9
ISSN: 03624803, 10991344
PubMed ID:
25690452
Organic Chemistry
Drug Discovery
Biochemistry
Spectroscopy
Analytical Chemistry
Radiology, Nuclear Medicine and imaging
Abstract
To synthesize (18) F-labeled positron emission tomography (PET) ligands, reliable labeling techniques inserting (18) F into a target molecule are necessary. The (18) F-fluorobenzene moiety has been widely utilized in the synthesis of (18) F-labeled compounds. The present study utilized [(18) F]-labeled aniline as intermediate in [(18) F]-radiolabeling chemistry for the facile radiosynthesis of 4-amino-N-(3-chloro-4-fluorophenyl)-N'-hydroxy-1,2,5-oxadiazole-3-carboximidamide ([(18) F]IDO5L) as indoleamine 2,3-dioxygenase 1 (IDO1) targeted tracer. IDO5L is a highly potent inhibitor of IDO1 with low nanomolar IC50 . [(18) F]IDO5L was synthesized via coupling [(18) F]3-chloro-4-fluoroaniline with carboximidamidoyl chloride as a potential PET probe for imaging IDO1 expression. Under the optimized labeling conditions, chemically and radiochemically pure (>98%) [(18) F]IDO5L was obtained with specific radioactivity ranging from 11 to 15 GBq/µmol at the end of synthesis within ~90 min, and the decay-corrected radiochemical yield was 18.2 ± 2.1% (n = 4).
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Huang X., GILLIES R. J., Tian H. Synthesis of [18F] 4-amino-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide (IDO5L): a novel potential PET probe for imaging of IDO1 expression // Journal of Labelled Compounds and Radiopharmaceuticals. 2015. Vol. 58. No. 4. pp. 156-162.
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Huang X., GILLIES R. J., Tian H. Synthesis of [18F] 4-amino-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide (IDO5L): a novel potential PET probe for imaging of IDO1 expression // Journal of Labelled Compounds and Radiopharmaceuticals. 2015. Vol. 58. No. 4. pp. 156-162.
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RIS
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TY - JOUR
DO - 10.1002/jlcr.3263
UR - https://doi.org/10.1002/jlcr.3263
TI - Synthesis of [18F] 4-amino-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide (IDO5L): a novel potential PET probe for imaging of IDO1 expression
T2 - Journal of Labelled Compounds and Radiopharmaceuticals
AU - Huang, Xuan
AU - GILLIES, ROBERT J.
AU - Tian, Haibin
PY - 2015
DA - 2015/02/18
PB - Wiley
SP - 156-162
IS - 4
VL - 58
PMID - 25690452
SN - 0362-4803
SN - 1099-1344
ER -
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@article{2015_Huang,
author = {Xuan Huang and ROBERT J. GILLIES and Haibin Tian},
title = {Synthesis of [18F] 4-amino-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide (IDO5L): a novel potential PET probe for imaging of IDO1 expression},
journal = {Journal of Labelled Compounds and Radiopharmaceuticals},
year = {2015},
volume = {58},
publisher = {Wiley},
month = {feb},
url = {https://doi.org/10.1002/jlcr.3263},
number = {4},
pages = {156--162},
doi = {10.1002/jlcr.3263}
}
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MLA
Copy
Huang, Xuan, et al. “Synthesis of [18F] 4-amino-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide (IDO5L): a novel potential PET probe for imaging of IDO1 expression.” Journal of Labelled Compounds and Radiopharmaceuticals, vol. 58, no. 4, Feb. 2015, pp. 156-162. https://doi.org/10.1002/jlcr.3263.