Chromenopyrazole-based High Affinity, Selective Fluorescent Ligands for Cannabinoid Type 2 Receptor
Cannabinoid type 2 receptor (CB2R) is an attractive target for the treatment of pain and inflammatory disorders. Availability of a selective CB2R fluorescent ligand to study CB2R expression and localization in healthy and disease conditions would greatly contribute to improving our understanding of...
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| Published in | ACS medicinal chemistry letters Vol. 10; no. 2; pp. 209 - 214 |
|---|---|
| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
14.02.2019
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1948-5875 1948-5875 |
| DOI | 10.1021/acsmedchemlett.8b00597 |
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| Abstract | Cannabinoid type 2 receptor (CB2R) is an attractive target for the treatment of pain and inflammatory disorders. Availability of a selective CB2R fluorescent ligand to study CB2R expression and localization in healthy and disease conditions would greatly contribute to improving our understanding of this receptor. Herein, we report a series of chromenopyrazole-based CB2R fluorescent ligands. The highest affinity fluorescent ligand was Cy5-containing 24 (hCB2R pK i = 7.38 ± 0.05), which had 131-fold selectivity over CB1R. In a cAMP BRET assay, 24 behaved as a potent CB2R inverse agonist. Widefield imaging experiments showed that 24 binds to CB2R in live cells with good selectivity and low levels of nonspecific fluorescence. The high affinity, selectivity, and suitable imaging properties of fluorescent ligand 24 make it a valuable tool for studying CB2R. |
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| AbstractList | Cannabinoid
type 2 receptor (CB
2
R) is an attractive
target for the treatment of pain and inflammatory disorders. Availability
of a selective CB
2
R fluorescent ligand to study CB
2
R expression and localization in healthy and disease conditions
would greatly contribute to improving our understanding of this receptor.
Herein, we report a series of chromenopyrazole-based CB
2
R fluorescent ligands. The highest affinity fluorescent ligand was
Cy5-containing
24
(hCB
2
R p
K
i
= 7.38 ± 0.05), which had 131-fold selectivity
over CB
1
R. In a cAMP BRET assay,
24
behaved
as a potent CB
2
R inverse agonist. Widefield imaging experiments
showed that
24
binds to CB
2
R in live cells
with good selectivity and low levels of nonspecific fluorescence.
The high affinity, selectivity, and suitable imaging properties of
fluorescent ligand
24
make it a valuable tool for studying
CB
2
R. Cannabinoid type 2 receptor (CB2R) is an attractive target for the treatment of pain and inflammatory disorders. Availability of a selective CB2R fluorescent ligand to study CB2R expression and localization in healthy and disease conditions would greatly contribute to improving our understanding of this receptor. Herein, we report a series of chromenopyrazole-based CB2R fluorescent ligands. The highest affinity fluorescent ligand was Cy5-containing 24 (hCB2R pK i = 7.38 ± 0.05), which had 131-fold selectivity over CB1R. In a cAMP BRET assay, 24 behaved as a potent CB2R inverse agonist. Widefield imaging experiments showed that 24 binds to CB2R in live cells with good selectivity and low levels of nonspecific fluorescence. The high affinity, selectivity, and suitable imaging properties of fluorescent ligand 24 make it a valuable tool for studying CB2R.Cannabinoid type 2 receptor (CB2R) is an attractive target for the treatment of pain and inflammatory disorders. Availability of a selective CB2R fluorescent ligand to study CB2R expression and localization in healthy and disease conditions would greatly contribute to improving our understanding of this receptor. Herein, we report a series of chromenopyrazole-based CB2R fluorescent ligands. The highest affinity fluorescent ligand was Cy5-containing 24 (hCB2R pK i = 7.38 ± 0.05), which had 131-fold selectivity over CB1R. In a cAMP BRET assay, 24 behaved as a potent CB2R inverse agonist. Widefield imaging experiments showed that 24 binds to CB2R in live cells with good selectivity and low levels of nonspecific fluorescence. The high affinity, selectivity, and suitable imaging properties of fluorescent ligand 24 make it a valuable tool for studying CB2R. Cannabinoid type 2 receptor (CB2R) is an attractive target for the treatment of pain and inflammatory disorders. Availability of a selective CB2R fluorescent ligand to study CB2R expression and localization in healthy and disease conditions would greatly contribute to improving our understanding of this receptor. Herein, we report a series of chromenopyrazole-based CB2R fluorescent ligands. The highest affinity fluorescent ligand was Cy5-containing 24 (hCB(2)R pK(i), = 7.38 +/- 0.05), which had 131-fold selectivity over CB1R. In a cAMP BRET assay, 24 behaved as a potent CB2R. inverse agonist. Widefield imaging experiments showed that 24 binds to CB2R in live cells with good selectivity and low levels of nonspecific fluorescence. The high affinity, selectivity, and suitable imaging properties of fluorescent ligand 24 make it a valuable tool for studying CB2R. Cannabinoid type 2 receptor (CB R) is an attractive target for the treatment of pain and inflammatory disorders. Availability of a selective CB R fluorescent ligand to study CB R expression and localization in healthy and disease conditions would greatly contribute to improving our understanding of this receptor. Herein, we report a series of chromenopyrazole-based CB R fluorescent ligands. The highest affinity fluorescent ligand was Cy5-containing (hCB R p = 7.38 ± 0.05), which had 131-fold selectivity over CB R. In a cAMP BRET assay, behaved as a potent CB R inverse agonist. Widefield imaging experiments showed that binds to CB R in live cells with good selectivity and low levels of nonspecific fluorescence. The high affinity, selectivity, and suitable imaging properties of fluorescent ligand make it a valuable tool for studying CB R. Cannabinoid type 2 receptor (CB2R) is an attractive target for the treatment of pain and inflammatory disorders. Availability of a selective CB2R fluorescent ligand to study CB2R expression and localization in healthy and disease conditions would greatly contribute to improving our understanding of this receptor. Herein, we report a series of chromenopyrazole-based CB2R fluorescent ligands. The highest affinity fluorescent ligand was Cy5-containing 24 (hCB2R pK i = 7.38 ± 0.05), which had 131-fold selectivity over CB1R. In a cAMP BRET assay, 24 behaved as a potent CB2R inverse agonist. Widefield imaging experiments showed that 24 binds to CB2R in live cells with good selectivity and low levels of nonspecific fluorescence. The high affinity, selectivity, and suitable imaging properties of fluorescent ligand 24 make it a valuable tool for studying CB2R. |
| Author | Grimsey, Natasha L Glass, Michelle Vernall, Andrea J Macdonald, Christa Singh, Sameek Oyagawa, Caitlin R. M |
| AuthorAffiliation | School of Pharmacy University of Otago University of Auckland Department of Pharmacology and Clinical Pharmacology, and Centre for Brain Research, School of Medical Sciences, Faculty of Medical and Health Sciences |
| AuthorAffiliation_xml | – name: University of Otago – name: University of Auckland – name: School of Pharmacy – name: Department of Pharmacology and Clinical Pharmacology, and Centre for Brain Research, School of Medical Sciences, Faculty of Medical and Health Sciences |
| Author_xml | – sequence: 1 givenname: Sameek surname: Singh fullname: Singh, Sameek organization: University of Otago – sequence: 2 givenname: Caitlin R. M surname: Oyagawa fullname: Oyagawa, Caitlin R. M organization: University of Auckland – sequence: 3 givenname: Christa surname: Macdonald fullname: Macdonald, Christa organization: University of Auckland – sequence: 4 givenname: Natasha L surname: Grimsey fullname: Grimsey, Natasha L organization: University of Auckland – sequence: 5 givenname: Michelle surname: Glass fullname: Glass, Michelle organization: University of Auckland – sequence: 6 givenname: Andrea J orcidid: 0000-0001-8056-0726 surname: Vernall fullname: Vernall, Andrea J email: andrea.vernall@otago.ac.nz organization: University of Otago |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30783505$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.1039/c3ob41221k 10.1080/13543776.2016.1193157 10.1080/00207454.2016.1257992 10.1021/acs.jmedchem.7b01811 10.1016/j.chembiol.2011.02.016 10.1369/0022155414530995 10.1039/C8MD00448J 10.1007/s00018-016-2300-4 10.1002/cmdc.201100568 10.1016/j.neuropharm.2015.04.033 10.1111/bph.12265 10.1021/jacs.7b11281 10.1021/acs.bioconjchem.7b00680 10.1080/17460441.2018.1518975 10.1002/anie.201200467 10.1124/mol.117.108605 10.1016/j.bcp.2012.02.014 10.1021/acs.jmedchem.6b00397 10.1021/bc400328m 10.1016/j.tips.2017.10.006 10.1016/j.ejmech.2017.11.076 10.1124/pr.110.003004 10.1124/pr.116.013243 10.1142/S1088424617500092 10.1124/pr.58.3.2 10.1039/c8md00448j |
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| Keywords | GPCR fluorescent ligand chemical tool cannabinoid type 2 receptor CB2 RECEPTOR ENDOCANNABINOID SYSTEM AGONISTS SCAFFOLD PROBES TOOLS |
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| References | ref9/cit9 ref6/cit6 ref3/cit3 ref18/cit18 ref11/cit11 ref25/cit25 ref16/cit16 ref14/cit14 ref8/cit8 ref5/cit5 ref2/cit2 Morales P. (ref23/cit23) 2018; 84 ref20/cit20 ref17/cit17 ref10/cit10 ref26/cit26 ref19/cit19 ref21/cit21 ref12/cit12 ref15/cit15 ref22/cit22 ref13/cit13 ref4/cit4 ref1/cit1 ref24/cit24 ref7/cit7 Iliopoulos-Tsoutsouvas, C (WOS:000451747000006) 2018; 13 Marchalant, Y (WOS:000337598700001) 2014; 62 Turcotte, C (WOS:000386696300006) 2016; 73 Lam, R (WOS:000425063400047) 2018; 61 Martin-Fontecha, M (WOS:000426144300018) 2018; 29 Martin-Couce, L (WOS:000305990800014) 2012; 51 Sexton, M (WOS:000291499600005) 2011; 18 Morales, Paula (BCI:BCI201800646249) 2018; 84 Vernall, AJ (WOS:000323800900014) 2013; 11 Pacher, P (WOS:000240465500004) 2006; 58 Stoddart, LA (WOS:000366228700007) 2015; 98 Pertwee, RG (WOS:000284214900003) 2010; 62 Vernall, AJ (WOS:000331909700002) 2014; 171 Stoddart, LA (WOS:000423456500006) 2018; 39 Morales, P (WOS:000380730600012) 2016; 59 Kleyer, J (WOS:000302435000009) 2012; 83 Martella, A (WOS:000409976400002) 2017; 92 Cooper, AG (WOS:000453225200008) 2018; 9 Morales, P (WOS:000396390700009) 2017; 21 Cumella, J (WOS:000300942300013) 2012; 7 Cooper, AG (WOS:000425198200059) 2018; 145 Soethoudt, M (WOS:000432753400008) 2018; 140 Cooper, A (WOS:000404236500004) 2017; 69 Zhang, SJ (WOS:000327413100016) 2013; 24 Morales, P (WOS:000378874200009) 2016; 26 Shang, YC (WOS:000405184600011) 2017; 127 |
| References_xml | – ident: ref25/cit25 doi: 10.1039/c3ob41221k – ident: ref5/cit5 doi: 10.1080/13543776.2016.1193157 – ident: ref4/cit4 doi: 10.1080/00207454.2016.1257992 – ident: ref11/cit11 doi: 10.1021/acs.jmedchem.7b01811 – ident: ref14/cit14 doi: 10.1016/j.chembiol.2011.02.016 – volume: 84 start-page: 164 year: 2018 ident: ref23/cit23 publication-title: Anal. Real Acad. Nac. F. – ident: ref8/cit8 doi: 10.1369/0022155414530995 – ident: ref17/cit17 doi: 10.1039/C8MD00448J – ident: ref3/cit3 doi: 10.1007/s00018-016-2300-4 – ident: ref21/cit21 doi: 10.1002/cmdc.201100568 – ident: ref9/cit9 doi: 10.1016/j.neuropharm.2015.04.033 – ident: ref10/cit10 doi: 10.1111/bph.12265 – ident: ref18/cit18 doi: 10.1021/jacs.7b11281 – ident: ref20/cit20 doi: 10.1021/acs.bioconjchem.7b00680 – ident: ref12/cit12 doi: 10.1080/17460441.2018.1518975 – ident: ref19/cit19 doi: 10.1002/anie.201200467 – ident: ref7/cit7 doi: 10.1124/mol.117.108605 – ident: ref26/cit26 doi: 10.1016/j.bcp.2012.02.014 – ident: ref22/cit22 doi: 10.1021/acs.jmedchem.6b00397 – ident: ref15/cit15 doi: 10.1021/bc400328m – ident: ref13/cit13 doi: 10.1016/j.tips.2017.10.006 – ident: ref16/cit16 doi: 10.1016/j.ejmech.2017.11.076 – ident: ref1/cit1 doi: 10.1124/pr.110.003004 – ident: ref6/cit6 doi: 10.1124/pr.116.013243 – ident: ref24/cit24 doi: 10.1142/S1088424617500092 – ident: ref2/cit2 doi: 10.1124/pr.58.3.2 – volume: 73 start-page: 4449 year: 2016 ident: WOS:000386696300006 article-title: The CB2 receptor and its role as a regulator of inflammation publication-title: CELLULAR AND MOLECULAR LIFE SCIENCES doi: 10.1007/s00018-016-2300-4 – volume: 26 start-page: 843 year: 2016 ident: WOS:000378874200009 article-title: Cannabinoid receptor 2 (CB2) agonists and antagonists: a patent update publication-title: EXPERT OPINION ON THERAPEUTIC PATENTS doi: 10.1080/13543776.2016.1193157 – volume: 18 start-page: 563 year: 2011 ident: WOS:000291499600005 article-title: NIR-mbc94, a Fluorescent Ligand that Binds to Endogenous CB2 Receptors and Is Amenable to High-Throughput Screening publication-title: CHEMISTRY & BIOLOGY doi: 10.1016/j.chembiol.2011.02.016 – volume: 62 start-page: 395 year: 2014 ident: WOS:000337598700001 article-title: Validating Antibodies to the Cannabinoid CB2 Receptor: Antibody Sensitivity Is Not Evidence of Antibody Specificity publication-title: JOURNAL OF HISTOCHEMISTRY & CYTOCHEMISTRY doi: 10.1369/0022155414530995 – volume: 51 start-page: 6896 year: 2012 ident: WOS:000305990800014 article-title: Chemical Probes for the Recognition of Cannabinoid Receptors in Native Systems publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201200467 – volume: 140 start-page: 6067 year: 2018 ident: WOS:000432753400008 article-title: Selective Photoaffinity Probe That Enables Assessment of Cannabinoid CB2 Receptor Expression and Ligand Engagement in Human Cells publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.7b11281 – volume: 24 start-page: 1907 year: 2013 ident: WOS:000327413100016 article-title: In Vivo Type 2 Cannabinoid Receptor-Targeted Tumor Optical Imaging Using a Near Infrared Fluorescent Probe publication-title: BIOCONJUGATE CHEMISTRY doi: 10.1021/bc400328m – volume: 62 start-page: 588 year: 2010 ident: WOS:000284214900003 article-title: International Union of Basic and Clinical Pharmacology. LXXIX. Cannabinoid Receptors and Their Ligands: Beyond CB1 and CB2 publication-title: PHARMACOLOGICAL REVIEWS doi: 10.1124/pr.110.003004 – volume: 171 start-page: 1073 year: 2014 ident: WOS:000331909700002 article-title: The evolving small-molecule fluorescent-conjugate toolbox for Class A GPCRs publication-title: BRITISH JOURNAL OF PHARMACOLOGY doi: 10.1111/bph.12265 – volume: 92 start-page: 389 year: 2017 ident: WOS:000409976400002 article-title: A Novel Selective Inverse Agonist of the CB2 Receptor as a Radiolabeled Tool Compound for Kinetic Binding Studies publication-title: MOLECULAR PHARMACOLOGY doi: 10.1124/mol.117.108605 – volume: 13 start-page: 933 year: 2018 ident: WOS:000451747000006 article-title: Fluorescent probes for G-protein-coupled receptor drug discovery publication-title: EXPERT OPINION ON DRUG DISCOVERY doi: 10.1080/17460441.2018.1518975 – volume: 84 start-page: 164 year: 2018 ident: BCI:BCI201800646249 article-title: The chromenopyrazole scaffold in the modulation of the endocannabinoid system: a broad therapeutic prospect publication-title: Anales de la Real Academia Nacional de Farmacia – volume: 145 start-page: 770 year: 2018 ident: WOS:000425198200059 article-title: Alkyl indole-based cannabinoid type 2 receptor tools: Exploration of linker and fluorophore attachment publication-title: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1016/j.ejmech.2017.11.076 – volume: 21 start-page: 67 year: 2017 ident: WOS:000396390700009 article-title: Synthesis of a novel CB2 cannabinoid-porphyrin conjugate based on an antitumor chromenopyrazoledione publication-title: JOURNAL OF PORPHYRINS AND PHTHALOCYANINES doi: 10.1142/S1088424617500092 – volume: 127 start-page: 812 year: 2017 ident: WOS:000405184600011 article-title: The central cannabinoid receptor type-2 (CB2) and chronic pain publication-title: INTERNATIONAL JOURNAL OF NEUROSCIENCE doi: 10.1080/00207454.2016.1257992 – volume: 9 start-page: 2055 year: 2018 ident: WOS:000453225200008 article-title: Development of selective, fluorescent cannabinoid type 2 receptor ligands based on a 1,8-naphthyridin-2-(1H)-one-3-carboxamide scaffold publication-title: MEDCHEMCOMM doi: 10.1039/c8md00448j – volume: 98 start-page: 48 year: 2015 ident: WOS:000366228700007 article-title: Probing the pharmacology of G protein-coupled receptors with fluorescent ligands publication-title: NEUROPHARMACOLOGY doi: 10.1016/j.neuropharm.2015.04.033 – volume: 59 start-page: 6753 year: 2016 ident: WOS:000380730600012 article-title: Chromenopyrazole, a Versatile Cannabinoid Scaffold with in Vivo Activity in a Model of Multiple Sclerosis publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/acs.jmedchem.6b00397 – volume: 7 start-page: 452 year: 2012 ident: WOS:000300942300013 article-title: Chromenopyrazoles: Non-psychoactive and Selective CB1 Cannabinoid Agonists with Peripheral Antinociceptive Properties publication-title: CHEMMEDCHEM doi: 10.1002/cmdc.201100568 – volume: 39 start-page: 136 year: 2018 ident: WOS:000423456500006 article-title: NanoBRET Approaches to Study Ligand Binding to GPCRs and RTKs publication-title: TRENDS IN PHARMACOLOGICAL SCIENCES doi: 10.1016/j.tips.2017.10.006 – volume: 83 start-page: 1393 year: 2012 ident: WOS:000302435000009 article-title: Cannabinoid receptor trafficking in peripheral cells is dynamically regulated by a binary biochemical switch publication-title: BIOCHEMICAL PHARMACOLOGY doi: 10.1016/j.bcp.2012.02.014 – volume: 29 start-page: 382 year: 2018 ident: WOS:000426144300018 article-title: A Fluorescent Probe to Unravel Functional Features of Cannabinoid Receptor CB1 in Human Blood and Tonsil Immune System Cells publication-title: BIOCONJUGATE CHEMISTRY doi: 10.1021/acs.bioconjchem.7b00680 – volume: 69 start-page: 316 year: 2017 ident: WOS:000404236500004 article-title: Chemical Tools for Studying Lipid-Binding Class A G Protein-Coupled Receptors publication-title: PHARMACOLOGICAL REVIEWS doi: 10.1124/pr.116.013243 – volume: 11 start-page: 5673 year: 2013 ident: WOS:000323800900014 article-title: Conversion of a non-selective adenosine receptor antagonist into A(3)-selective high affinity fluorescent probes using peptide-based linkers publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY doi: 10.1039/c3ob41221k – volume: 58 start-page: 389 year: 2006 ident: WOS:000240465500004 article-title: The endocannabinoid system as an emerging target of pharmacotherapy publication-title: PHARMACOLOGICAL REVIEWS doi: 10.1124/pr.58.3.2 – volume: 61 start-page: 1316 year: 2018 ident: WOS:000425063400047 article-title: Fluorescently Labeled Morphine Derivatives for Bioimaging Studies publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/acs.jmedchem.7b01811 |
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| Snippet | Cannabinoid type 2 receptor (CB2R) is an attractive target for the treatment of pain and inflammatory disorders. Availability of a selective CB2R fluorescent... Cannabinoid type 2 receptor (CB R) is an attractive target for the treatment of pain and inflammatory disorders. Availability of a selective CB R fluorescent... Cannabinoid type 2 receptor (CB 2 R) is an attractive target for the treatment of pain and inflammatory disorders. Availability of a selective CB 2 R... |
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| Title | Chromenopyrazole-based High Affinity, Selective Fluorescent Ligands for Cannabinoid Type 2 Receptor |
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