Hyperpolarisation of mirfentanil by SABRE in the presence of heroin
Hyperpolarisation of mirfentanil by SABRE in the presence of heroin
Mirfentanil, a fentanyl derivative that is a μ-opioid partial agonist, is hyperpolarised via Signal Amplification By Reversible Exchange (SABRE), a para-hydrogen-based technique. [Ir(IMes)(COD)Cl] (IMes=1,3-bis(2,4,6-trimethylphenyl)imidazole-2-ylidene, COD=cyclooctadiene) was employed as the polarisation transfer catalyst. Following polarisation transfer at 6.5 mT, the pyrazine-protons were enhanced by 78-fold (polarisation, P=0.04 %). The complex [Ir(IMes)(H)
2(mirfentanil)
2(MeOH)]
+ is proposed to form based on the observation of two hydrides at δ −22.9 (trans to mirfentanil) and −24.7 (trans to methanol). In a mixture of mirfentanil and heroin, the former could be detected using SABRE at concentrations less than 1 % w/w. At the lowest concentration analyzed, the amount of mirfentanil present was 0.18 mg (812 μM) and produced a signal enhancement of −867-fold (P=0.42 %). following polarisation transfer at 6.5 mT.
Mirfentanil, NMR, SABRE, hyperpolarisation, opioid
1059-1064
Robertson, T.B.R.
957b392c-1212-4721-bd6d-d1e00ed50a09
Gilbert, N
e3fffb23-185f-44d8-930b-619b50308022
Sutcliffe, O.B.
86aa588b-938d-443f-a232-094187621b1e
Mewis, R.E.
4a5f2448-51e8-4b7f-94c8-f91f866d79f4
4 June 2021
Robertson, T.B.R.
957b392c-1212-4721-bd6d-d1e00ed50a09
Gilbert, N
e3fffb23-185f-44d8-930b-619b50308022
Sutcliffe, O.B.
86aa588b-938d-443f-a232-094187621b1e
Mewis, R.E.
4a5f2448-51e8-4b7f-94c8-f91f866d79f4
Robertson, T.B.R., Gilbert, N, Sutcliffe, O.B. and Mewis, R.E.
(2021)
Hyperpolarisation of mirfentanil by SABRE in the presence of heroin.
Chemphyschem, 22 (11), .
(doi:10.1002/cphc.202100165).
Abstract
Mirfentanil, a fentanyl derivative that is a μ-opioid partial agonist, is hyperpolarised via Signal Amplification By Reversible Exchange (SABRE), a para-hydrogen-based technique. [Ir(IMes)(COD)Cl] (IMes=1,3-bis(2,4,6-trimethylphenyl)imidazole-2-ylidene, COD=cyclooctadiene) was employed as the polarisation transfer catalyst. Following polarisation transfer at 6.5 mT, the pyrazine-protons were enhanced by 78-fold (polarisation, P=0.04 %). The complex [Ir(IMes)(H)
2(mirfentanil)
2(MeOH)]
+ is proposed to form based on the observation of two hydrides at δ −22.9 (trans to mirfentanil) and −24.7 (trans to methanol). In a mixture of mirfentanil and heroin, the former could be detected using SABRE at concentrations less than 1 % w/w. At the lowest concentration analyzed, the amount of mirfentanil present was 0.18 mg (812 μM) and produced a signal enhancement of −867-fold (P=0.42 %). following polarisation transfer at 6.5 mT.
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Accepted/In Press date: 19 April 2021
e-pub ahead of print date: 11 May 2021
Published date: 4 June 2021
Additional Information:
Funding Information:
REM is grateful to Manchester Metropolitan University for a Vice Chancellor studentship for TBRR. The Natural Sciences and Engineering Research Council of Canada (396154510) and Fonds de Recherche du Québec – Nature et Technologie (206375) are thanked for funding for NG. Oxford Instruments are thanked for their technical support.
Funding Information:
REM is grateful to Manchester Metropolitan University for a Vice Chancellor studentship for TBRR. The Natural Sciences and Engineering Research Council of Canada (396154510) and Fonds de Recherche du Qu?bec ? Nature et Technologie (206375) are thanked for funding for NG. Oxford Instruments are thanked for their technical support.
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© 2021 Wiley-VCH GmbH
Keywords:
Mirfentanil, NMR, SABRE, hyperpolarisation, opioid
Identifiers
Local EPrints ID: 448964
URI: http://eprints.soton.ac.uk/id/eprint/448964
ISSN: 1439-7641
PURE UUID: 55f4f2e4-2902-45f0-a416-f78fd8abcd37
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Date deposited: 12 May 2021 16:30
Last modified: 17 Mar 2024 04:04
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Author:
N Gilbert
Author:
O.B. Sutcliffe
Author:
R.E. Mewis
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