GMP Compliant Synthesis of [18F]Canagliflozin, a Novel PET Tracer for the Sodium−Glucose Cotransporter 2

Sjoukje van der Hoek; Inês F.  Antunes; Khaled A.  Attia; Olivier  Jacquet; André Heeres; Marian  Bulthuis; Rolf Zijlma; Hendrikus H.  Boersma; Harry van Goor; Ton J. Visser; Hiddo J. L.  Heerspink; Philip H.  Elsinga; Jasper  Stevens

doi:10.1021/acs.jmedchem.1c01269

GMP Compliant Synthesis of [18F]Canagliflozin, a Novel PET Tracer for the Sodium−Glucose Cotransporter 2

Sjoukje van der Hoek, Inês F. Antunes, Khaled A. Attia, Olivier Jacquet, André Heeres, Marian Bulthuis, Rolf Zijlma, Hendrikus H. Boersma, Harry van Goor, Ton J. Visser, Hiddo J. L. Heerspink, Philip H. Elsinga, Jasper Stevens

Rijksuniversiteit Groningen, Universitair Medisch Centrum Groningen, Afdeling Klinische Farmacie en Farmacologie
Rijksuniversiteit Groningen, Universitair Medisch Centrum Groningen, Afdeling Nucleaire Geneeskunde en Moleculaire Beeldvorming
Symeres BV
Rijksuniversiteit Groningen, Universitair Medisch Centrum Groningen, Afdeling Pathologie en Medische Biologie

Onderzoeksoutput: Article › Academic › peer review

Samenvatting

Inhibition of the sodium–glucose cotransporter 2 (SGLT2) by canagliflozin in type 2 diabetes mellitus results in large between-patient variability in clinical response. To better understand this variability, the positron emission tomography (PET) tracer [18F]canagliflozin was developed via a Cu-mediated 18F-fluorination of its boronic ester precursor with a radiochemical yield of 2.0 ± 1.9% and a purity of >95%. The GMP automated synthesis originated [18F]canagliflozin with a yield of 0.5–3% (n = 4) and a purity of >95%. Autoradiography showed [18F]canagliflozin binding in human kidney sections containing SGLT2. Since [18F]canagliflozin is the isotopologue of the extensively characterized drug canagliflozin and thus shares its toxicological and pharmacological characteristics, it enables its immediate use in patients.

Originele taal-2	English
Pagina's (van-tot)	16641–16649
Aantal pagina's	9
Tijdschrift	Journal of Medicinal Chemistry
Volume	64
Nummer van het tijdschrift	22
DOI's	https://doi.org/10.1021/acs.jmedchem.1c01269
Status	Published - 8 nov. 2021

Keywords

canagliflozine

Toegang tot document

10.1021/acs.jmedchem.1c01269Licentie: CC BY-NC-ND

11 Article
1 Report
1 Poster
1 Patent

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van der Loo, C., Kaniraj, J. P., Wang, T., Pouwer, K., Broekman, O., Borst, M., Heeres, A., Deuss, P. & Minnaard, A., 5 okt. 2023, In: Organic and Biomolecular Chemistry. 21, 41, blz. 8372-8378 7 blz.
Onderzoeksoutput: Article › Academic › peer review

Open Access
Advantages of Producing Aromatics from Propene over Ethene Using Zeolite-Based Catalysts
Butolia, P. S., Xi, X., Winkelman, J. G. M., Stuart, M. C. A., van Akker, M., Heeres, A., Heeres, H. J. & Xie, J., 11 okt. 2022, In: Chemie Ingenieur Technik - CIT. 94, 11, blz. 1845-1852 8 blz.
Onderzoeksoutput: Article › Academic › peer review

Open Access
A time- and space-resolved catalyst deactivation study on the conversion of glycerol to aromatics using H-ZSM-5
He, S., Goldhoorn, H. R., Tegudeer, Z., Chandel, A., Heeres, A., Stuart, M. C. A. & Heeres, H. J., 15 apr. 2022, In: Chemical Engineering Journal. 434, 134620.
Onderzoeksoutput: Article › Academic › peer review

Open Access

6 Invited talk
1 Oral presentation

De biobased/circulaire transitie (Hanze) - Konnect-lezing Eemshaven
Heeres, A. (Speaker)
8 feb. 2023
Activiteit: Invited talk
Kick-off Interreg EMPATHI: End-of-life options for PHA‘s
Heeres, A. (Speaker)
19 apr. 2023
Activiteit: Invited talk
Biobased/circular chemistry at the Hanze.
Heeres, A. (Speaker) & Keller, E. (Speaker)
2 jun. 2023
Activiteit: Invited talk

Citeer dit

van der Hoek, S., Antunes, I. F., Attia, K. A., Jacquet, O., Heeres, A., Bulthuis, M., Zijlma, R., Boersma, H. H., van Goor, H., Visser, T. J., Heerspink, H. J. L., Elsinga, P. H., & Stevens, J. (2021). GMP Compliant Synthesis of [18F]Canagliflozin, a Novel PET Tracer for the Sodium−Glucose Cotransporter 2. Journal of Medicinal Chemistry, 64(22), 16641–16649. https://doi.org/10.1021/acs.jmedchem.1c01269

@article{e8f3cd38c4d749efadb9b247fe2349d4,

title = "GMP Compliant Synthesis of [18F]Canagliflozin, a Novel PET Tracer for the Sodium−Glucose Cotransporter 2",

abstract = "Inhibition of the sodium–glucose cotransporter 2 (SGLT2) by canagliflozin in type 2 diabetes mellitus results in large between-patient variability in clinical response. To better understand this variability, the positron emission tomography (PET) tracer [18F]canagliflozin was developed via a Cu-mediated 18F-fluorination of its boronic ester precursor with a radiochemical yield of 2.0 ± 1.9% and a purity of >95%. The GMP automated synthesis originated [18F]canagliflozin with a yield of 0.5–3% (n = 4) and a purity of >95%. Autoradiography showed [18F]canagliflozin binding in human kidney sections containing SGLT2. Since [18F]canagliflozin is the isotopologue of the extensively characterized drug canagliflozin and thus shares its toxicological and pharmacological characteristics, it enables its immediate use in patients.",

keywords = "canagliflozine, PET tracer, glucose, canagliflozin",

author = "{van der Hoek}, Sjoukje and Antunes, {In{\^e}s F.} and Attia, {Khaled A.} and Olivier Jacquet and Andr{\'e} Heeres and Marian Bulthuis and Rolf Zijlma and Boersma, {Hendrikus H.} and {van Goor}, Harry and Visser, {Ton J.} and Heerspink, {Hiddo J. L.} and Elsinga, {Philip H.} and Jasper Stevens",

year = "2021",

month = nov,

day = "8",

doi = "10.1021/acs.jmedchem.1c01269",

language = "English",

volume = "64",

pages = "16641–16649",

journal = "Journal of Medicinal Chemistry",

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publisher = "American Chemical Society",

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van der Hoek, S, Antunes, IF, Attia, KA, Jacquet, O, Heeres, A, Bulthuis, M, Zijlma, R, Boersma, HH, van Goor, H, Visser, TJ, Heerspink, HJL, Elsinga, PH & Stevens, J 2021, 'GMP Compliant Synthesis of [18F]Canagliflozin, a Novel PET Tracer for the Sodium−Glucose Cotransporter 2', Journal of Medicinal Chemistry, vol. 64, nr. 22, blz. 16641–16649. https://doi.org/10.1021/acs.jmedchem.1c01269

TY - JOUR

T1 - GMP Compliant Synthesis of [18F]Canagliflozin, a Novel PET Tracer for the Sodium−Glucose Cotransporter 2

AU - van der Hoek, Sjoukje

AU - Antunes, Inês F.

AU - Attia, Khaled A.

AU - Jacquet, Olivier

AU - Heeres, André

AU - Bulthuis, Marian

AU - Zijlma, Rolf

AU - Boersma, Hendrikus H.

AU - van Goor, Harry

AU - Visser, Ton J.

AU - Heerspink, Hiddo J. L.

AU - Elsinga, Philip H.

AU - Stevens, Jasper

PY - 2021/11/8

Y1 - 2021/11/8

N2 - Inhibition of the sodium–glucose cotransporter 2 (SGLT2) by canagliflozin in type 2 diabetes mellitus results in large between-patient variability in clinical response. To better understand this variability, the positron emission tomography (PET) tracer [18F]canagliflozin was developed via a Cu-mediated 18F-fluorination of its boronic ester precursor with a radiochemical yield of 2.0 ± 1.9% and a purity of >95%. The GMP automated synthesis originated [18F]canagliflozin with a yield of 0.5–3% (n = 4) and a purity of >95%. Autoradiography showed [18F]canagliflozin binding in human kidney sections containing SGLT2. Since [18F]canagliflozin is the isotopologue of the extensively characterized drug canagliflozin and thus shares its toxicological and pharmacological characteristics, it enables its immediate use in patients.

AB - Inhibition of the sodium–glucose cotransporter 2 (SGLT2) by canagliflozin in type 2 diabetes mellitus results in large between-patient variability in clinical response. To better understand this variability, the positron emission tomography (PET) tracer [18F]canagliflozin was developed via a Cu-mediated 18F-fluorination of its boronic ester precursor with a radiochemical yield of 2.0 ± 1.9% and a purity of >95%. The GMP automated synthesis originated [18F]canagliflozin with a yield of 0.5–3% (n = 4) and a purity of >95%. Autoradiography showed [18F]canagliflozin binding in human kidney sections containing SGLT2. Since [18F]canagliflozin is the isotopologue of the extensively characterized drug canagliflozin and thus shares its toxicological and pharmacological characteristics, it enables its immediate use in patients.

KW - canagliflozine

KW - PET tracer

KW - glucose

KW - canagliflozin

U2 - 10.1021/acs.jmedchem.1c01269

DO - 10.1021/acs.jmedchem.1c01269

M3 - Article

SN - 0022-2623

VL - 64

SP - 16641

EP - 16649

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

IS - 22

ER -

GMP Compliant Synthesis of [18F]Canagliflozin, a Novel PET Tracer for the Sodium−Glucose Cotransporter 2

Samenvatting

Keywords

Toegang tot document

Vingerafdruk

Onderzoekersoutput

Substituted anilides from chitin-based 3-acetamido-furfural

Advantages of Producing Aromatics from Propene over Ethene Using Zeolite-Based Catalysts

A time- and space-resolved catalyst deactivation study on the conversion of glycerol to aromatics using H-ZSM-5

Activiteiten

De biobased/circulaire transitie (Hanze) - Konnect-lezing Eemshaven

Kick-off Interreg EMPATHI: End-of-life options for PHA‘s

Biobased/circular chemistry at the Hanze.

Citeer dit