Synthesis and testing of a p‐H2 hyperpolarized 13C probe based on the pyrazolo[1,5‐a]pyrimidineacetamide DPA‐713, an MRI vector to target the peripheral benzodiazepine receptors

Cerutti, Erika; Viale, Alessandra; Damont, Annelaure; Dollé, Frédéric; Aime, Silvio

doi:10.1002/mrc.2839

Cited by 5 publications

(3 citation statements)

References 34 publications

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“…The relaxation data were interpreted in terms of overall reorientation and internal rotation of the phenyl groups. Cerutti et al 224 described a procedure for synthesis and testing of a 13 C labelled alkyne, related to a pharmacologically interesting compound, which could be para-hydrogenated leading to a 13 C hyperpolarized alkene. The hyperpolarization could be transferred to a carboxylate carbon with a long T 1, useful for imaging.…”

Section: Non-electrolyte Solutionsmentioning

confidence: 99%

Nuclear spin relaxation in liquids and gases

Kowalewski¹

2013

Nuclear Magnetic Resonance

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This report reviews the progress in the field of NMR relaxation in fluids. The emphasis is on comparatively simple liquids and solutions of physico-chemical and chemical interest, in analogy with the previous periods, but selected biophysicsrelated topics and relaxation-related work on more complex systems (macromolecular solutions, liquid crystalline systems, glassy and porous materials) are also covered. The period under review is from June 2011 through May 2012. Some earlier works, overlooked in last year's chapter, are also included. The outline of this chapter is as follows: section 2 which follows the introduction covers the general, physical and experimental aspects of nuclear spin relaxation in liquids and is further divided in seven subsections. The first two are fairly general and the following three discuss more specific aspects of spin-1/2 systems. The last two subsections cover quadrupolar nuclei and paramagnetic systems, respectively. Section 3 deals with applications of NMR relaxation in liquids, starting with pure liquids and continuing with solutions of low-molecular weight compounds. It also includes a selection of works on solutions of biological macromolecules and other complex systems. The progress in the field of relaxation in gases is described in section 4.

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Section: Non-electrolyte Solutionsmentioning

confidence: 99%

Nuclear spin relaxation in liquids and gases

Kowalewski¹

2013

Nuclear Magnetic Resonance

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“… Some of the substrates used in different parahydrogen hyperpolarization methods: the red dots refer to hyperpolarized 13 C, the green dots to 15 N. PHIP substrates: hydroxylethyl acrylate (HEA) 1 , fumarate 2 , maleic anhydride 3 , phospho enoyl pyruvate 4 ,, 5 , 6 , 7 , 8 , 9 , 10 . Molecules can be labelled with unsaturated moieties, for instance: propargylic group 11 to obtain propargyl‐choline 12 ; [41] aminoacids derivatives 13–14 ; [56] labels for peptides 15 ; [39] butynoic acid 16 has been used as a label for glucose 17 and the vector DPA‐713 . PHIP‐SAH substrates: 19–20 , 21 , 22–23 ,,,, 24 .…”

Section: Parahydrogenation Substratesmentioning

confidence: 99%

“…[55] Molecules can be labelled with unsaturated moieties, for instance: propargylic group 11 to obtain propargyl-choline 12; [41] aminoacids derivatives 13-14; [56] labels for peptides 15; [39] butynoic acid 16 has been used as a label for glucose 17 [40] and the vector DPA-713. [57] PHIP-SAH substrates: 19-20, [43] 21, [58] 22-23, [33,43,59,60] 24. [58] SABRE substrates: 25,26, [42] 27, 28, [42] [61] 29,30, [62] 31,32.…”

Section: Parahydrogenation Substratesmentioning

confidence: 99%

ParaHydrogen Hyperpolarized Substrates for Molecular Imaging Studies

Cavallari

Carrera

Reineri

2017

Israel Journal of Chemistry

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Parahydrogen induced polarization (PHIP) is a chemistry based, cheap and easy to handle hyperpolarization method that allows to increase the sensitivity of magnetic resonance signals of several orders of magnitude. This powerful tool has not coalesced in the field of biomedical studies due to the lack of suitable hyperpolarization substrates, of commercial parahydrogen polarizers and to the presence of metal complex in the solutions of products. Here is reported an overview of the recent advances in these fields, with particular attention to the issues that have been tackled in order to allow the translation of parahydrogen based hyperpolarization methods into a widely applicable molecular imaging tool for biomedical research.

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2‐Aryl‐2,4‐dihydro‐5H‐[1,2,3]triazolo[4,5‐d]pyrimidin‐5‐ones as a New Platform for the Design and Synthesis of Biosensors and Chemosensors

et al. 2020

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2‐Aryl‐2,4‐dihydro‐5H‐[1,2,3]triazolo[4,5‐d]pyrimidin‐5‐ones (DTPs), which may be considered as analogues of 8‐azapurines, were synthesised. Their structural aspects in the ground and excited states, electronic distributions, and non‐covalent intramolecular interactions were studied using time‐dependent density functional theory. Photophysical investigations demonstrated the variability of the absorption and emission parameters of the DTPs depending on their structure, microenvironment, and external stimuli. The aggregation‐induced emission enhancement effect was confirmed by studying the emission of DTPs in the solid state and by spectral titrations in H2O‐dimethyl sulfoxide (DMSO) and EtOH‐DMSO mixtures. Further investigation revealed the selective sensitivity of DTPs to acids, which strongly depended on their structure. Reversible interactions were found between the DTPs and HCl and subsequently triethylamine, both as vapour stimuli and in solution. Cell imaging experiments showed the potential of the DTPs in fluorescence microscopy bioimaging applications. These findings show that DTPs can be used to fabricate bio‐ and chemosensors.

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Synthesis and testing of a p‐H₂ hyperpolarized ¹³C probe based on the pyrazolo[1,5‐a]pyrimidineacetamide DPA‐713, an MRI vector to target the peripheral benzodiazepine receptors

Cited by 5 publications

References 34 publications

Nuclear spin relaxation in liquids and gases

Nuclear spin relaxation in liquids and gases

ParaHydrogen Hyperpolarized Substrates for Molecular Imaging Studies

2‐Aryl‐2,4‐dihydro‐5H‐[1,2,3]triazolo[4,5‐d]pyrimidin‐5‐ones as a New Platform for the Design and Synthesis of Biosensors and Chemosensors

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