Synthesis of [18F]FMISO, a hypoxia-specific imaging probe for PET, an overview from a radiochemist’s perspective

Kniess, Torsten; Zessin, Jörg; Mäding, Peter; Kuchar, Manuela; Kiss, Oliver; Kopka, Klaus

doi:10.1186/s41181-023-00190-7

EJNMMI Radiopharmacy and Chemistry

Table 1 Summary of [¹⁸F]FMISO manufacturing methods,

From: Synthesis of [¹⁸F]FMISO, a hypoxia-specific imaging probe for PET, an overview from a radiochemist’s perspective

Precursor	Radio synthesis method	Purify-cation	Radio synthesis time [min]	Yield [#]	Radio-chemical purity	Molar activity [GBq/µmol]	Reference
1-Epoxy-propyl-2-nitroimidazole	Manual	HPLC	n.d	1% RCY	n.d	n.d	Jerabek t al. 1986
Epoxypropyl tosylate, 2-nitro-imidazole	Manual	HPLC	90	7–12% AY	n.d	14,8	Hwang et al. 1989
Epoxypropyl tosylate, 2-nitro-imidazole	Manual	HPLC	140	40% RCY	n.d	24	Grierson et al. 1989
Epoxypropyl tosylate, 2-nitro-imidazole	Semi-automated	HPLC	70	40% AY	> 98%	n.d	Mccarthy et al. 1993
NITTP	Manual	SPE	45–50	55–80% RCY	n.d	22	Lim et al. 1993
NIATP	Manual	SPE	60–70	12–18% AY	> 99%	74	Cherif et al. 1994
NITTP	Manual	HPLC	5–80	60–86% AY	n.d	n.d	Patt et al. 1999
Epoxypropyl tosylate, 2-nitro-imidazole	Manual	HPLC	180	13% AY	> 99%	n.d	Kamarainen et al. 2004
NITTP	Automated	SPE	50	21% RCY	> 97%	n.d	Kamarainen et al. 2004
NITTP	Automated	SPE	40	51% RCY	> 95%	n.d	Tang et al. 2005
NITTP	Automated	HPLC	60	60% RCY	> 95%	n.d	Tang et al. 2005
NITTP	Manual	HPLC	80	30–40% RCY	n.d	n.d	Adamsen et al. 2005
NITTP	Cassette based	HPLC	70	54% RCY	98,2%	337	Oh et al 2005
NIATP	Automated	SPE	65	30% AY	> 97%	n.d	Chang et al. 2007
NITTP	Automated	SPE	50	55% RCY	> 98%	370	Wang et al. 2009
NITTP	Automated	SPE	40	38% AY	> 95%	n.d	Nandy et al. 2010
NITTP	Microfluidic system	HPLC	60	58% RCY	> 99%	138	Yokell et al. 2012
NITTP	Cassette based	SPE	44	25% AY	> 98%	n.d	Lee et al. 2013
NITTP	Cassette based	SPE	52	41% AY	n.d	n.d	Krcal et al. 2013
NITTP	Automated	SPE	35	50% RCY	> 98%	200	Blom et al. 2014
NITTP	Microfluidic system	HPLC	106	28% AY	> 99%	119	Zheng et al. 2015
(R/S)-1-Epoxy-propyl-2-nitroimidazole	Automated	SPE	120	(R)-: 2% (S)-: 7% AY	n.d	100	Revunov et al. 2015
NITTP	Automated	SPE	21	40% RCY	> 95%	n.d	Fernandez-Maza et al. 2018
Epoxypropyl tosylate, 2-nitroimidazole	Automated	HPLC	75	26% AY	> 99%	110	Ohkubo et al. 2021
NITTP	Automated	SPE	31	56% AY	99,5%	n.d	Cucchi et al. 2022

[#] RCY = radiochemical yield, AY = activity yield (Coenen et al. 2017)

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