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:https://doi.org/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

Biobased Chemistry and Refinery

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
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

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

10 Article
1 Report
1 Poster
1 Patent

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Onderzoeksoutput: Article › Academic › peer review

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Open Access
Binding of the Dual-Action Anti-Parkinsonian Drug AG-0029 to Dopamine D2 and Histamine H3 Receptors: A PET Study in Healthy Rats
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Onderzoeksoutput: Article › Academic › peer review

Open Access

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

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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 = "https://doi.org/10.1021/acs.jmedchem.1c01269",

language = "English",

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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 - https://doi.org/10.1021/acs.jmedchem.1c01269

DO - https://doi.org/10.1021/acs.jmedchem.1c01269

M3 - Article

VL - 64

SP - 16641

EP - 16649

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

SN - 0022-2623

IS - 22

ER -

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

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Keywords

Toegang tot document

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Onderzoekersoutput

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

Binding of the Dual-Action Anti-Parkinsonian Drug AG-0029 to Dopamine D2 and Histamine H3 Receptors: A PET Study in Healthy Rats

Citeer dit