BIOMAT Database Logo BIOMAT Database Logo

Synthesis and characterization of high-affinity 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene-labeled fluorescent ligands for human β-adrenoceptors. 2011

Jillian G Baker, and Luke A Adams, and Karolina Salchow, and Shailesh N Mistry, and Richard J Middleton, and Stephen J Hill, and Barrie Kellam
School of Pharmacy, Centre for Biomolecular Sciences, University of Nottingham, University Park, Nottingham NG7 2RD, United Kingdom.

The growing practice of exploiting noninvasive fluorescence-based techniques to study G protein-coupled receptor pharmacology at the single cell and single molecule level demands the availability of high-quality fluorescent ligands. To this end, this study evaluated a new series of red-emitting ligands for the human β-adrenoceptor family. Upon the basis of the orthosteric ligands propranolol, alprenolol, and pindolol, the synthesized linker-modified congeners were coupled to the commercially available fluorophore BODIPY 630/650-X. This yielded high-affinity β-adrenoceptor fluorescent ligands for both the propranolol and alprenolol derivatives; however, the pindolol-based products displayed lower affinity. A fluorescent diethylene glycol linked propranolol derivative (18a) had the highest affinity (log K(D) of -9.53 and -8.46 as an antagonist of functional β2- and β1-mediated responses, respectively). Imaging studies with this compound further confirmed that it can be employed to selectively label the human β2-adrenoceptor in single living cells, with receptor-associated binding prevented by preincubation with the nonfluorescent β2-selective antagonist 3-(isopropylamino)-1-[(7-methyl-4-indanyl)oxy]butan-2-ol (ICI 118551) ( J. Cardiovasc. Pharmacol.1983, 5, 430-437. ).

UI MeSH Term Description Entries
D008024 Ligands A molecule that binds to another molecule, used especially to refer to a small molecule that binds specifically to a larger molecule, e.g., an antigen binding to an antibody, a hormone or neurotransmitter binding to a receptor, or a substrate or allosteric effector binding to an enzyme. Ligands are also molecules that donate or accept a pair of electrons to form a coordinate covalent bond with the central metal atom of a coordination complex. (From Dorland, 27th ed) Ligand
D010869 Pindolol A moderately lipophilic beta blocker (ADRENERGIC BETA-ANTAGONISTS). It is non-cardioselective and has intrinsic sympathomimetic actions, but little membrane-stabilizing activity. (From Martindale, The Extra Pharmocopoeia, 30th ed, p638) Prindolol,LB-46,Visken,LB 46,LB46
D011433 Propranolol A widely used non-cardioselective beta-adrenergic antagonist. Propranolol has been used for MYOCARDIAL INFARCTION; ARRHYTHMIA; ANGINA PECTORIS; HYPERTENSION; HYPERTHYROIDISM; MIGRAINE; PHEOCHROMOCYTOMA; and ANXIETY but adverse effects instigate replacement by newer drugs. Dexpropranolol,AY-20694,Anaprilin,Anapriline,Avlocardyl,Betadren,Dociton,Inderal,Obsidan,Obzidan,Propanolol,Propranolol Hydrochloride,Rexigen,AY 20694,AY20694,Hydrochloride, Propranolol
D011869 Radioligand Assay Quantitative determination of receptor (binding) proteins in body fluids or tissue using radioactively labeled binding reagents (e.g., antibodies, intracellular receptors, plasma binders). Protein-Binding Radioassay,Radioreceptor Assay,Assay, Radioligand,Assay, Radioreceptor,Assays, Radioligand,Assays, Radioreceptor,Protein Binding Radioassay,Protein-Binding Radioassays,Radioassay, Protein-Binding,Radioassays, Protein-Binding,Radioligand Assays,Radioreceptor Assays
D001896 Boron Compounds Inorganic or organic compounds that contain boron as an integral part of the molecule. Borides,Compounds, Boron
D003412 Cricetulus A genus of the family Muridae consisting of eleven species. C. migratorius, the grey or Armenian hamster, and C. griseus, the Chinese hamster, are the two species used in biomedical research. Hamsters, Armenian,Hamsters, Chinese,Hamsters, Grey,Armenian Hamster,Armenian Hamsters,Chinese Hamster,Chinese Hamsters,Grey Hamster,Grey Hamsters,Hamster, Armenian,Hamster, Chinese,Hamster, Grey
D005456 Fluorescent Dyes Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags. Flourescent Agent,Fluorescent Dye,Fluorescent Probe,Fluorescent Probes,Fluorochrome,Fluorochromes,Fluorogenic Substrates,Fluorescence Agents,Fluorescent Agents,Fluorogenic Substrate,Agents, Fluorescence,Agents, Fluorescent,Dyes, Fluorescent,Probes, Fluorescent,Substrates, Fluorogenic
D006224 Cricetinae A subfamily in the family MURIDAE, comprising the hamsters. Four of the more common genera are Cricetus, CRICETULUS; MESOCRICETUS; and PHODOPUS. Cricetus,Hamsters,Hamster
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000318 Adrenergic beta-Agonists Drugs that selectively bind to and activate beta-adrenergic receptors. Adrenergic beta-Receptor Agonists,beta-Adrenergic Agonists,beta-Adrenergic Receptor Agonists,Adrenergic beta-Agonist,Adrenergic beta-Receptor Agonist,Betamimetics,Receptor Agonists, beta-Adrenergic,Receptors Agonists, Adrenergic beta,beta-Adrenergic Agonist,beta-Adrenergic Receptor Agonist,Adrenergic beta Agonist,Adrenergic beta Agonists,Adrenergic beta Receptor Agonist,Adrenergic beta Receptor Agonists,Agonist, Adrenergic beta-Receptor,Agonist, beta-Adrenergic,Agonist, beta-Adrenergic Receptor,Agonists, Adrenergic beta-Receptor,Agonists, beta-Adrenergic,Agonists, beta-Adrenergic Receptor,Receptor Agonist, beta-Adrenergic,Receptor Agonists, beta Adrenergic,beta Adrenergic Agonist,beta Adrenergic Agonists,beta Adrenergic Receptor Agonist,beta Adrenergic Receptor Agonists,beta-Agonist, Adrenergic,beta-Agonists, Adrenergic,beta-Receptor Agonist, Adrenergic,beta-Receptor Agonists, Adrenergic

Related Publications

Jillian G Baker, and Luke A Adams, and Karolina Salchow, and Shailesh N Mistry, and Richard J Middleton, and Stephen J Hill, and Barrie Kellam
Synthesis and characterization of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY)-labeled fluorescent ligands for the mu opioid receptor.
December 1997, Biochemical pharmacology,
Jillian G Baker, and Luke A Adams, and Karolina Salchow, and Shailesh N Mistry, and Richard J Middleton, and Stephen J Hill, and Barrie Kellam
4,4-Difluoro-1,3,5,7-tetra-methyl-4-bora-3a,4a-diaza-s-indacene.
August 2008, Acta crystallographica. Section E, Structure reports online,
Jillian G Baker, and Luke A Adams, and Karolina Salchow, and Shailesh N Mistry, and Richard J Middleton, and Stephen J Hill, and Barrie Kellam
4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene as a bright fluorescent label for DNA.
April 2011, The Journal of organic chemistry,
Jillian G Baker, and Luke A Adams, and Karolina Salchow, and Shailesh N Mistry, and Richard J Middleton, and Stephen J Hill, and Barrie Kellam
Functionalization of the 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) core.
May 2008, Bioorganic & medicinal chemistry letters,
Jillian G Baker, and Luke A Adams, and Karolina Salchow, and Shailesh N Mistry, and Richard J Middleton, and Stephen J Hill, and Barrie Kellam
4,4-Difluoro-1,3,5,7-tetra-methyl-8-penta-fluoro-phenyl-4-bora-3a,4a-diaza-s-indacene.
March 2010, Acta crystallographica. Section E, Structure reports online,
Jillian G Baker, and Luke A Adams, and Karolina Salchow, and Shailesh N Mistry, and Richard J Middleton, and Stephen J Hill, and Barrie Kellam
Synthesis of the core compound of the BODIPY dye class: 4,4'-difluoro-4-bora-(3a,4a)-diaza-s-indacene.
July 2009, Journal of fluorescence,
Jillian G Baker, and Luke A Adams, and Karolina Salchow, and Shailesh N Mistry, and Richard J Middleton, and Stephen J Hill, and Barrie Kellam
[A synthesis and properties of new 4,4-difluoro-3a,4a-diaza-s-indacene (BODIPY))-labeled lipids].
January 2006, Bioorganicheskaia khimiia,
Jillian G Baker, and Luke A Adams, and Karolina Salchow, and Shailesh N Mistry, and Richard J Middleton, and Stephen J Hill, and Barrie Kellam
4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes modified for extended conjugation and restricted bond rotations.
May 2000, The Journal of organic chemistry,
Jillian G Baker, and Luke A Adams, and Karolina Salchow, and Shailesh N Mistry, and Richard J Middleton, and Stephen J Hill, and Barrie Kellam
Disabling photoinduced electron transfer in 4,4-difluoro-8(-4'-hydroxyphenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene by phosphorylation.
January 2008, Journal of fluorescence,
Jillian G Baker, and Luke A Adams, and Karolina Salchow, and Shailesh N Mistry, and Richard J Middleton, and Stephen J Hill, and Barrie Kellam
Photoresponsiveness of Anthracene-Based Supramolecular Polymers Regulated via a σ-Platinated 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene Photosensitizer.
September 2019, Inorganic chemistry,
Copied contents to your clipboard!