Home / Publications / A metal-templated synthesis of precursors for (2S)- and (2R)-2-(3-[18F]fluoropropyl)tyrosines as potential radiotracers for positron emission tomography

A metal-templated synthesis of precursors for (2S)- and (2R)-2-(3-[18F]fluoropropyl)tyrosines as potential radiotracers for positron emission tomography

Tat'yana F Savel'yeva 1
Tat'yana F Savel'yeva
Zalina Taymurazovna Gugkaeva 1
Zalina Taymurazovna Gugkaeva
Yulia Vladimirovna Nelyubina 1
Yulia Vladimirovna Nelyubina
Alexander Fedorovich Smol'yakov 1
Alexander Fedorovich Smol'yakov
Margarita Alekseevna Moskalenko 1
Margarita Alekseevna Moskalenko
Vladimir Anatol'evich Larionov 1
Vladimir Anatol'evich Larionov
1 A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation
Published 2024-06-19
CommunicationVolume 34, Issue 4, 496-498
4
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Savel'yeva T. F. et al. A metal-templated synthesis of precursors for (2S)- and (2R)-2-(3-[18F]fluoropropyl)tyrosines as potential radiotracers for positron emission tomography // Mendeleev Communications. 2024. Vol. 34. No. 4. pp. 496-498.
GOST all authors (up to 50) Copy
Savel'yeva T. F., Gugkaeva Z. T., Nelyubina Y. V., Smol'yakov A. F., Moskalenko M. A., Larionov V. A., Maleev V. I. A metal-templated synthesis of precursors for (2S)- and (2R)-2-(3-[18F]fluoropropyl)tyrosines as potential radiotracers for positron emission tomography // Mendeleev Communications. 2024. Vol. 34. No. 4. pp. 496-498.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2024.06.008
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.06.008
TI - A metal-templated synthesis of precursors for (2S)- and (2R)-2-(3-[18F]fluoropropyl)tyrosines as potential radiotracers for positron emission tomography
T2 - Mendeleev Communications
AU - Savel'yeva, Tat'yana F
AU - Gugkaeva, Zalina Taymurazovna
AU - Nelyubina, Yulia Vladimirovna
AU - Smol'yakov, Alexander Fedorovich
AU - Moskalenko, Margarita Alekseevna
AU - Larionov, Vladimir Anatol'evich
AU - Maleev, Victor Ivanovich
PY - 2024
DA - 2024/06/19
PB - Mendeleev Communications
SP - 496-498
IS - 4
VL - 34
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2024_Savel'yeva,
author = {Tat'yana F Savel'yeva and Zalina Taymurazovna Gugkaeva and Yulia Vladimirovna Nelyubina and Alexander Fedorovich Smol'yakov and Margarita Alekseevna Moskalenko and Vladimir Anatol'evich Larionov and Victor Ivanovich Maleev},
title = {A metal-templated synthesis of precursors for (2S)- and (2R)-2-(3-[18F]fluoropropyl)tyrosines as potential radiotracers for positron emission tomography},
journal = {Mendeleev Communications},
year = {2024},
volume = {34},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.06.008},
number = {4},
pages = {496--498},
doi = {10.1016/j.mencom.2024.06.008}
}
MLA
Cite this
MLA Copy
Savel'yeva, Tat'yana F., et al. “A metal-templated synthesis of precursors for (2S)- and (2R)-2-(3-[18F]fluoropropyl)tyrosines as potential radiotracers for positron emission tomography.” Mendeleev Communications, vol. 34, no. 4, Jun. 2024, pp. 496-498. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.06.008.

Keywords

18F-labelled amino acids
asymmetric synthesis
nickel(ii) complexes.
nucleophilic substitution
tyrosine

Abstract

New asymmetric metal-templated synthesis of enantiomers of (2S)- and (2R)-2-(3-[19F]fluoropropyl)tyrosine precursors were obtained based on a chiral NiII complex of the Schiff base derived from (S)-2-[N-(N’-benzylprolyl)amino]-benzaldehyde and racemic tyrosine in five steps. The free tyrosine derivatives which can be obtained upon decomplexation seem promising radiotracers for positron emission tomography imaging provided the introduction of 18F isotope.

References

.
OLEX2: a complete structure solution, refinement and analysis program
Dolomanov O.V., Bourhis L.J., Gildea R.J., Howard J.A., Puschmann H.
Journal of Applied Crystallography, 2009
.
A short history of SHELX
Sheldrick G.M.
Acta Crystallographica Section A Foundations of Crystallography, 2007
.
General method of diastereo- and enantioselective synthesis of β-hydroxy-α-amino acids by condensation of aldehydes and ketones with glycine
Belokon Y.N., Bulychev A.G., Vitt S.V., Struchkov Y.T., Batsanov A.S., Timofeeva T.V., Tsyryapkin V.A., Ryzhov M.G., Lysova L.A.
Journal of the American Chemical Society, 1985
.
Methods for (11) C- and (18) F-labelling of amino acids and derivatives for positron emission tomography imaging.
Ermert J., Coenen H.H.
Journal of Labelled Compounds and Radiopharmaceuticals, 2013
.
No carrier added synthesis of O-(2'-[18F]fluoroethyl)-L-tyrosine via a novel type of chiral enantiomerically pure precursor, NiII complex of a (S)-tyrosine Schiff base.
Krasikova R.N., Kuznetsova O.F., Fedorova O.S., Maleev V.I., Saveleva T.F., Belokon Y.N.
Bioorganic and Medicinal Chemistry, 2008
.
Preparation of labeled aromatic amino acids via late-stage 18F-fluorination of chiral nickel and copper complexes
Craig A., Kolks N., Urusova E.A., Zischler J., Brugger M., Endepols H., Neumaier B., Zlatopolskiy B.D.
Chemical Communications, 2020
.
THE METABOLISM OF TUMORS IN THE BODY
Warburg O., Wind F., Negelein E.
Journal of General Physiology, 1927
.
Enantioselectivity of nickel(II) and copper(II) complexes of Schiff bases derived from amino acids and (S)-o-[(N-benzylprolyl)amino]-acetophenone or (S)-o-[(N-benzylprolyl)amino]benzaldehyde. Crystal and molecular structures of [Ni{(S)-bap-(S)-Val}] and [Cu{(S)-bap-(S)-Val}]
Belokon Y.N., Maleyev V.I., Vitt S.V., Ryzhov M.G., Kondrashov Y.D., Golubev S.N., Vauchskii Y.P., Kazika A.I., Novikova M.I., Krasutskii P.A., Yurchenko A.G., Dubchak I.L., Shklover V.E., Struchkov Y.T., Bakhmutov V.I., et. al.
Journal of the Chemical Society Dalton Transactions, 1985
.
Asymmetric synthesis of 6-18F-L-FDOPA using chiral Nickel(II) complexes
Krasikova R.N., Kuznetsova O.F., Fedorova O.S., Mosevich I.K., Maleev V.I., Belokon Y.N., Savel’eva T.F., Sagiyan A.S., Dadayan S.A., Petrosyan A.A.
Radiochemistry, 2007
.
Synthesis of O-(1′-[18F]fluoropropan-2′-yl)-l-tyrosine (1-[18F]FPT) via Ni(II) complex of (S) tyrosine schiff’s base precursor
.
THE [14C]DEOXYGLUCOSE METHOD FOR THE MEASUREMENT OF LOCAL CEREBRAL GLUCOSE UTILIZATION: THEORY, PROCEDURE, AND NORMAL VALUES IN THE CONSCIOUS AND ANESTHETIZED ALBINO RAT 1
Sokoloff L., Reivich M., Kennedy C., Rosiers M.H., Patlak C.S., Pettigrew K.D., Sakurada O., Shinohara M.
Journal of Neurochemistry, 1977
.
Radiolabeled Amino Acids for Oncologic Imaging
Huang C., McConathy J.
Journal of Nuclear Medicine, 2013
.
11C- and 18F-labelled tryptophans as PET-tracers for imaging of altered tryptophan metabolism in age-associated disorders
Zlatopolskiy B.D., Endepols H., Krasikova R.N., Fedorova O.S., Ermert J., Neumaier B.
Russian Chemical Reviews, 2020
.
Antuganov D.O., Nadporojskii M.A., Kondratenko Y.A.
Mendeleev Communications, 2022