Detection of apoptosis by PET/CT with the diethyl ester of [ 18F]ML-10 and fluorescence imaging with a dansyl analogue

Manikandan Kadirvel; Michael Fairclough; Christopher Cawthorne; Emily J. Rowling; Muhammad Babur; Adam McMahon; Paul Birkket; Alison Smigova; Sally Freeman; Kaye J. Williams; Gavin Brown

doi:10.1016/j.bmc.2013.11.019

Detection of apoptosis by PET/CT with the diethyl ester of [ ¹⁸F]ML-10 and fluorescence imaging with a dansyl analogue

Manikandan Kadirvel, Michael Fairclough, Christopher Cawthorne, Emily J. Rowling, Muhammad Babur, Adam McMahon, Paul Birkket, Alison Smigova, Sally Freeman, Kaye J. Williams, Gavin Brown^*

^*Corresponding author for this work

Chemical Engineering

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

The diethyl ester of [¹⁸F]ML-10 is a small molecule apoptotic PET probe for cancer studies. Here we report a novel multi-step synthesis of the diethyl ester of ML-10 in excellent yields via fluorination using Xtal-Fluor-E. In addition, a one-pot radiosynthesis of the diethyl ester of [ ¹⁸F]ML-10 from nucleophilic [¹⁸F]fluoride was completed in 23% radiochemical yield (decay corrected). The radiochemical purity of the product was ≥99%. The diethyl ester of [¹⁸F]ML-10 was used in vivo to detect apoptosis in the testes of mice. In parallel studies, the dansyl-ML-10 diethyl ester was prepared and used to detect apoptotic cells in an in vitro cell based assay.

Original language	English
Pages (from-to)	341-349
Number of pages	9
Journal	Bioorganic and Medicinal Chemistry
Volume	22
Issue number	1
Early online date	20 Nov 2013
DOIs	https://doi.org/10.1016/j.bmc.2013.11.019
Publication status	Published - 1 Jan 2014

Bibliographical note

Funding Information:
We thank Katrina Copeland, Michael Green, Jamil Gregory, Marc Radigois, Gemma Chapman, Jonathan Lowe, Neil O’Hara, Biljana Arsic, Fariba Fanimarvasti, Soraya Alnabulsi, Anthony Archer and Charles Fletcher for technical assistance. The Bioimaging Facility microscopes used in this study were purchased with grants from BBSRC , Wellcome and the University of Manchester Strategic Fund . Special thanks go to Peter March, Roger Meadows and Steven Marsden for their help with the microscopy.

Keywords

Apoptosis
Fluorine-18
ML-10
Nucleophilic fluorination
PET/CT
XtalFluor-E

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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Cite this

Kadirvel, M., Fairclough, M., Cawthorne, C., Rowling, E. J., Babur, M., McMahon, A., Birkket, P., Smigova, A., Freeman, S., Williams, K. J., & Brown, G. (2014). Detection of apoptosis by PET/CT with the diethyl ester of [ ¹⁸F]ML-10 and fluorescence imaging with a dansyl analogue. Bioorganic and Medicinal Chemistry, 22(1), 341-349. https://doi.org/10.1016/j.bmc.2013.11.019

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title = "Detection of apoptosis by PET/CT with the diethyl ester of [ 18F]ML-10 and fluorescence imaging with a dansyl analogue",

abstract = "The diethyl ester of [18F]ML-10 is a small molecule apoptotic PET probe for cancer studies. Here we report a novel multi-step synthesis of the diethyl ester of ML-10 in excellent yields via fluorination using Xtal-Fluor-E. In addition, a one-pot radiosynthesis of the diethyl ester of [ 18F]ML-10 from nucleophilic [18F]fluoride was completed in 23% radiochemical yield (decay corrected). The radiochemical purity of the product was ≥99%. The diethyl ester of [18F]ML-10 was used in vivo to detect apoptosis in the testes of mice. In parallel studies, the dansyl-ML-10 diethyl ester was prepared and used to detect apoptotic cells in an in vitro cell based assay.",

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author = "Manikandan Kadirvel and Michael Fairclough and Christopher Cawthorne and Rowling, {Emily J.} and Muhammad Babur and Adam McMahon and Paul Birkket and Alison Smigova and Sally Freeman and Williams, {Kaye J.} and Gavin Brown",

note = "Funding Information: We thank Katrina Copeland, Michael Green, Jamil Gregory, Marc Radigois, Gemma Chapman, Jonathan Lowe, Neil O{\textquoteright}Hara, Biljana Arsic, Fariba Fanimarvasti, Soraya Alnabulsi, Anthony Archer and Charles Fletcher for technical assistance. The Bioimaging Facility microscopes used in this study were purchased with grants from BBSRC , Wellcome and the University of Manchester Strategic Fund . Special thanks go to Peter March, Roger Meadows and Steven Marsden for their help with the microscopy. ",

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Kadirvel, M, Fairclough, M, Cawthorne, C, Rowling, EJ, Babur, M, McMahon, A, Birkket, P, Smigova, A, Freeman, S, Williams, KJ & Brown, G 2014, 'Detection of apoptosis by PET/CT with the diethyl ester of [ ¹⁸F]ML-10 and fluorescence imaging with a dansyl analogue', Bioorganic and Medicinal Chemistry, vol. 22, no. 1, pp. 341-349. https://doi.org/10.1016/j.bmc.2013.11.019

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AU - Rowling, Emily J.

AU - Babur, Muhammad

AU - McMahon, Adam

AU - Birkket, Paul

AU - Smigova, Alison

AU - Freeman, Sally

AU - Williams, Kaye J.

AU - Brown, Gavin

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