NTI4F: a non-peptide fluorescent probe selective for functional delta opioid receptors

Kshirsagar, Tushar; Nakano, Albert H.; Law, Ping Yee; Elde, Robert; Portoghese, Philip S.

doi:10.1016/s0304-3940(98)00379-6

Cited by 30 publications

(41 citation statements)

References 17 publications

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“…47,48,59,[80][81][82] In previous studies [33][34][35][36] it had been shown that the implementation of a linker on the guanidinyl NH leads to molecules which can retain affinity, antagonistic activity and selectivity for the KOR. Inspired by these studies, and also by investigations highlighting the contribution of the linker's length and physicochemical properties in avoiding non-specific binding and preserving the pharmacological profile of the prototype ligand, 60,61,[83][84][85] we designed three sets of fluorescent probes: a) compounds 9a and 9b, which bear a 11-bond aliphatic linker (Scheme 1); b) compound 13, which bears a 17-bond linker with the incorporation of a diglycine moiety (Scheme 2); c) compounds 17a and 17b, which bears a 23-bond linker with the incorporation of a tetraglycine moiety (Scheme 2). Regarding their synthesis, an orthogonal approach was necessary in order to simultaneously accommodate the selective protection of primary amines and the protection of the guanidinyl NH throughout the synthetic scheme.…”

Section: Introductionmentioning

confidence: 99%

Investigation of Inactive-State κ Opioid Receptor Homodimerization via Single-Molecule Microscopy Using New Antagonistic Fluorescent Probes

et al. 2020

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Where a licence is displayed above, please note the terms and conditions of the licence govern your use of this document.When citing, please reference the published version. Take down policyWhile the University of Birmingham exercises care and attention in making items available there are rare occasions when an item has been uploaded in error or has been deemed to be commercially or otherwise sensitive.

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Section: Introductionmentioning

confidence: 99%

Investigation of Inactive-State κ Opioid Receptor Homodimerization via Single-Molecule Microscopy Using New Antagonistic Fluorescent Probes

et al. 2020

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“…Nevertheless, a wide range of fluorescent conjugates of delta agonists and antagonists have been synthesized and are commercially available (Cell Aura Technologies Ltd. and Cisbio Bioassays). Fluorescent antagonists have proved useful to examine delta opioid receptor distribution in living cells (Kshirsagar et al, 1998; Balboni et al, 2004; Cohen et al, 2016); while agonists have been used to study delta opioid receptor inter-nalization and trafficking in vivo (Arttamangkul et al, 2000; Cahill et al, 2001; Lee et al, 2002). …”

Section: Introductionmentioning

confidence: 99%

The delta opioid receptor tool box

2016

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In recent years, the delta opioid receptor has attracted Increasing Interest as a target for the treatment of chronic pain and emotional disorders. Due to their therapeutic potential, numerous tools have been developed to study the delta opioid receptor from both a molecular and a functional perspective. This review summarizes the most commonly available tools, with an emphasis on their use and limitations. Here, we describe (1) the cell-based assays used to study the delta opioid receptor. (2) The features of several delta opioid receptor ligands, including peptide and non-peptide drugs. (3) The existing approaches to detect delta opioid receptors in fixed tissue, and debates that surround these techniques. (4) Behavioral assays used to study the in vivo effects of delta opioid receptor agonists; including locomotor stimulation and convulsions that are induced by some ligands, but not others. (5) The characterization of genetically modified mice used specifically to study the delta opioid receptor. Overall, this review aims to provide a guideline for the use of these tools with the final goal of increasing our understanding of delta opioid receptor physiology.

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“…Fluorescent ligands selective for δORs mostly consist of peptide‐based, natural products as pharmacophores, which are not part of our summary. Kshirsagar and colleagues developed δOR‐selective fluorescent ligands 93a‐b by merging naltrindole (NTI) and fluorescein (Scheme 53A) [191] . They found that substitution at 7′ position and incorporation of a tetraglycyl‐linker improved selectivity, yielding a fluorescent probe for δOR imaging.…”

Section: Fluorescent Ligands For Gpcrsmentioning

confidence: 99%

Lighting Up the Plasma Membrane: Development and Applications of Fluorescent Ligands for Transmembrane Proteins

Borgarelli

Klingl

Escamilla-Ayala

et al. 2021

Chemistry A European J

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Despite the fact that transmembrane proteins represent the main therapeutic targets for decades, complete and in‐depth knowledge about their biochemical and pharmacological profiling is not fully available. In this regard, target‐tailored small‐molecule fluorescent ligands are a viable approach to fill in the missing pieces of the puzzle. Such tools, coupled with the ability of high‐precision optical techniques to image with an unprecedented resolution at a single‐molecule level, helped unraveling many of the conundrums related to plasma proteins’ life‐cycle and druggability. Herein, we review the recent progress made during the last two decades in fluorescent ligand design and potential applications in fluorescence microscopy of voltage‐gated ion channels, ligand‐gated ion channels and G‐coupled protein receptors.

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NTI4F: a non-peptide fluorescent probe selective for functional delta opioid receptors

Cited by 30 publications

References 17 publications

Investigation of Inactive-State κ Opioid Receptor Homodimerization via Single-Molecule Microscopy Using New Antagonistic Fluorescent Probes

Investigation of Inactive-State κ Opioid Receptor Homodimerization via Single-Molecule Microscopy Using New Antagonistic Fluorescent Probes

The delta opioid receptor tool box

Lighting Up the Plasma Membrane: Development and Applications of Fluorescent Ligands for Transmembrane Proteins

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