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

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

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

André Heeres, Sjoukje van der Hoek, Inês F. Antunes, Khaled A. Attia, Olivier Jacquet, 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
Rijksuniversiteit Groningen, Universitair Medisch Centrum Groningen, Afdeling Pathologie en Medische Biologie

Onderzoeksoutput: Article › Academic › peer review

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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	Dutch
Tijdschrift	Journal of Medicinal Chemistry
Status	Published - 8 nov. 2021

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Keywords

natrium-glucose-cotransporter
natrium
glucose
diabetes

Toegang tot document

acs.jmedchem.1c01269Final published version, 4,06 MBLicentie: CC BY-NC-ND

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Citeer dit

@article{ac3a9150ca874674add4fdf20ac170a3,

title = "GMP Compliant Synthesis of 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 = "natrium-glucose-cotransporter, natrium, glucose, diabetes, sodium–glucose cotransporter, sodium, glucose, diabetes",

author = "Andr{\'e} Heeres and \{van der Hoek\}, Sjoukje and Antunes, \{In{\^e}s F.\} and Attia, \{Khaled A.\} and Olivier Jacquet 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",

language = "Dutch",

journal = "Journal of Medicinal Chemistry",

issn = "0022-2623",

publisher = "American Chemical Society",

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TY - JOUR

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

AU - Heeres, André

AU - van der Hoek, Sjoukje

AU - Antunes, Inês F.

AU - Attia, Khaled A.

AU - Jacquet, Olivier

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 - natrium-glucose-cotransporter

KW - natrium

KW - glucose

KW - diabetes

KW - sodium–glucose cotransporter

KW - sodium

KW - glucose

KW - diabetes

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

M3 - Article

SN - 0022-2623

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

ER -

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

Samenvatting

Duurzame ontwikkelingsdoelstellingen van de VN

Keywords

Toegang tot document

Andere bestanden en links

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

Sustainable building blocks at the Hanze

Citeer dit