Radiosynthesis and evaluation of novel 18F labeled PET ligands for imaging monoacylglycerol lipase

Monoacylglycerol lipase (MAGL) is a 33 kDa cytosolic serine hydrolase that is widely distributed in the central nervous system and peripheral tissues. MAGL hydrolyzes monoacylglycerols into fatty acids and glycerol, playing a crucial role in endocannabinoid degradation. Inhibition of MAGL in the bra...

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Veröffentlicht in:European journal of medicinal chemistry 2025-03, Vol.285, p.117246, Article 117246
Hauptverfasser: Li, Yinlong, Mori, Wakana, Chaudhary, Ahmad, Zhao, Chunyu, Yamasaki, Tomoteru, Zhang, Zachary, Feng, Siyan, Ware, Tim, Rong, Jian, Fujinaga, Masayuki, Chen, Jiahui, Kumata, Katsushi, Zhang, Yiding, Hu, Kuan, Xie, Lin, Zhou, Xin, Song, Zhendong, Gao, Yabiao, Sun, Zhenkun, Patel, Jimmy S., Zhai, Chuangyan, Yuan, Katherine Y., Collier, Thomas L., Ran, Chongzhao, Collin, Ludovic, Haider, Achi, Grether, Uwe, Wittwer, Matthias B., Cravatt, Benjamin F., Zhang, Ming-Rong, Liang, Steven H.
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container_title European journal of medicinal chemistry
container_volume 285
creator Li, Yinlong
Mori, Wakana
Chaudhary, Ahmad
Zhao, Chunyu
Yamasaki, Tomoteru
Zhang, Zachary
Feng, Siyan
Ware, Tim
Rong, Jian
Fujinaga, Masayuki
Chen, Jiahui
Kumata, Katsushi
Zhang, Yiding
Hu, Kuan
Xie, Lin
Zhou, Xin
Song, Zhendong
Gao, Yabiao
Sun, Zhenkun
Patel, Jimmy S.
Zhai, Chuangyan
Yuan, Katherine Y.
Collier, Thomas L.
Ran, Chongzhao
Collin, Ludovic
Haider, Achi
Grether, Uwe
Wittwer, Matthias B.
Cravatt, Benjamin F.
Zhang, Ming-Rong
Liang, Steven H.
description Monoacylglycerol lipase (MAGL) is a 33 kDa cytosolic serine hydrolase that is widely distributed in the central nervous system and peripheral tissues. MAGL hydrolyzes monoacylglycerols into fatty acids and glycerol, playing a crucial role in endocannabinoid degradation. Inhibition of MAGL in the brain elevates levels of 2-arachidonoylglycerol and leads to decreased pro-inflammatory prostaglandin and thromboxane production. As such, MAGL is considered a potential target for treating neuropsychiatric disorders, metabolic syndromes, and cancer. Based on a novel spirocyclic system, we synthesized two fluorinated carbamate scaffolds as reversible MAGL inhibitors (epimers: (R)-6, IC50 = 18.6 nM and (S)-6, IC50 = 1.6 nM). In vitro autoradiography studies of [18F](R)-6 (codenamed [18F]MAGL-2304) and [18F](S)-6 (codenamed [18F]MAGL-2305) demonstrated heterogeneous distribution and specific binding affinity to MAGL-rich brain regions. Autoradiography with MAGL knockout mouse brain tissues confirmed the binding specificity of [18F](S)-6. Dynamic PET imaging studies revealed that [18F](S)-6 exhibited limited brain uptake and homogenous distribution in rat brains. In vivo P-gp inhibition enhanced [18F](S)-6 uptake in the brain, suggesting that [18F](S)-6 constitutes a P-gp efflux substrate. This research could provide new directions in the design of MAGL PET ligands that are based on spirocyclic scaffolds. [Display omitted] •MAGL is considered a potential target for treating neurological disorders.•Two novel MAGL PET imaging radioligands were synthesized and evaluated in rodents.•[18F](S)-6 exhibited high affinity to MAGL-rich regions of rodent brain sections.•Invivo PET imaging of [18F](S)-6 showed heterogeneous rat brain distribution, consistent with reported MAGL expression.
doi_str_mv 10.1016/j.ejmech.2025.117246
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MAGL hydrolyzes monoacylglycerols into fatty acids and glycerol, playing a crucial role in endocannabinoid degradation. Inhibition of MAGL in the brain elevates levels of 2-arachidonoylglycerol and leads to decreased pro-inflammatory prostaglandin and thromboxane production. As such, MAGL is considered a potential target for treating neuropsychiatric disorders, metabolic syndromes, and cancer. Based on a novel spirocyclic system, we synthesized two fluorinated carbamate scaffolds as reversible MAGL inhibitors (epimers: (R)-6, IC50 = 18.6 nM and (S)-6, IC50 = 1.6 nM). In vitro autoradiography studies of [18F](R)-6 (codenamed [18F]MAGL-2304) and [18F](S)-6 (codenamed [18F]MAGL-2305) demonstrated heterogeneous distribution and specific binding affinity to MAGL-rich brain regions. Autoradiography with MAGL knockout mouse brain tissues confirmed the binding specificity of [18F](S)-6. Dynamic PET imaging studies revealed that [18F](S)-6 exhibited limited brain uptake and homogenous distribution in rat brains. In vivo P-gp inhibition enhanced [18F](S)-6 uptake in the brain, suggesting that [18F](S)-6 constitutes a P-gp efflux substrate. This research could provide new directions in the design of MAGL PET ligands that are based on spirocyclic scaffolds. 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MAGL hydrolyzes monoacylglycerols into fatty acids and glycerol, playing a crucial role in endocannabinoid degradation. Inhibition of MAGL in the brain elevates levels of 2-arachidonoylglycerol and leads to decreased pro-inflammatory prostaglandin and thromboxane production. As such, MAGL is considered a potential target for treating neuropsychiatric disorders, metabolic syndromes, and cancer. Based on a novel spirocyclic system, we synthesized two fluorinated carbamate scaffolds as reversible MAGL inhibitors (epimers: (R)-6, IC50 = 18.6 nM and (S)-6, IC50 = 1.6 nM). In vitro autoradiography studies of [18F](R)-6 (codenamed [18F]MAGL-2304) and [18F](S)-6 (codenamed [18F]MAGL-2305) demonstrated heterogeneous distribution and specific binding affinity to MAGL-rich brain regions. Autoradiography with MAGL knockout mouse brain tissues confirmed the binding specificity of [18F](S)-6. 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MAGL hydrolyzes monoacylglycerols into fatty acids and glycerol, playing a crucial role in endocannabinoid degradation. Inhibition of MAGL in the brain elevates levels of 2-arachidonoylglycerol and leads to decreased pro-inflammatory prostaglandin and thromboxane production. As such, MAGL is considered a potential target for treating neuropsychiatric disorders, metabolic syndromes, and cancer. Based on a novel spirocyclic system, we synthesized two fluorinated carbamate scaffolds as reversible MAGL inhibitors (epimers: (R)-6, IC50 = 18.6 nM and (S)-6, IC50 = 1.6 nM). In vitro autoradiography studies of [18F](R)-6 (codenamed [18F]MAGL-2304) and [18F](S)-6 (codenamed [18F]MAGL-2305) demonstrated heterogeneous distribution and specific binding affinity to MAGL-rich brain regions. Autoradiography with MAGL knockout mouse brain tissues confirmed the binding specificity of [18F](S)-6. Dynamic PET imaging studies revealed that [18F](S)-6 exhibited limited brain uptake and homogenous distribution in rat brains. In vivo P-gp inhibition enhanced [18F](S)-6 uptake in the brain, suggesting that [18F](S)-6 constitutes a P-gp efflux substrate. This research could provide new directions in the design of MAGL PET ligands that are based on spirocyclic scaffolds. [Display omitted] •MAGL is considered a potential target for treating neurological disorders.•Two novel MAGL PET imaging radioligands were synthesized and evaluated in rodents.•[18F](S)-6 exhibited high affinity to MAGL-rich regions of rodent brain sections.•Invivo PET imaging of [18F](S)-6 showed heterogeneous rat brain distribution, consistent with reported MAGL expression.</abstract><pub>Elsevier Masson SAS</pub><doi>10.1016/j.ejmech.2025.117246</doi><orcidid>https://orcid.org/0000-0003-1413-6315</orcidid></addata></record>
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title Radiosynthesis and evaluation of novel 18F labeled PET ligands for imaging monoacylglycerol lipase
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