Conjugates of catecholamines. VII. Synthesis and β‐adrenergic activity of peptide catecholamine conjugates†
- 1 March 1987
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 29 (3) , 300-317
- https://doi.org/10.1111/j.1399-3011.1987.tb02258.x
Abstract
A series of novel catecholamine derivatives has been prepared in which one of the N-methyl substituents of isoproterenol has been extended by a spacer consisting of a chain of four methylenes which terminates with an amide linkage to a peptide, the point of attachment being via the aromatic amino group of p-aminophenylalanine. In one of the derivatives, two catecholamines are attached to the same peptide in this manner. The peptides, which range in size from three to eight amino acid residues and contain phenylalanine, glycine, and L-.alpha.-amino-.delta.-hydroxyvaleric acid, were synthesized via stepwise and fragment condensation techniques. The .beta.-adrenergic agonist activities of the derivatives were evaluated in vitro by measuring the intracellular accumulation of cyclic AMP in S49 mouse lymphoma cells.Keywords
This publication has 19 references indexed in Scilit:
- Stereostructure-activity relationship of opioid agonist and antagonist bivalent ligands. Evidence for bridging between vicinal opioid receptorsJournal of Medicinal Chemistry, 1985
- Conjugates of Catecholamines. 5. Synthesis and β-Adrenergic Activity of N-(Aminoalkyl)norepinephrine DerivativesJournal of Medicinal Chemistry, 1985
- Conjugates of Catecholamines. 6. Synthesis and β-Adrenergic Activity of N - (Hydroxyalkyl)catecholamine DerivativesJournal of Medicinal Chemistry, 1985
- Conjugates of catecholamines. III. Synthesis and characterization of monodisperse oligopeptides conjugates related to isoproterenolInternational Journal of Peptide and Protein Research, 1983
- Conjugates of catecholamines. 1. N-Alkyl-functionalized carboxylic acid congeners and amides related to isoproterenolJournal of Medicinal Chemistry, 1983
- Some novel approaches to the design and synthesis of peptide–catecholamine conjugatesBiopolymers, 1983
- Chemistry of Alpha- and Beta-Adrenoceptor Agonists and AntagonistsPublished by Springer Nature ,1980
- Stability and Biological Activity of Catecholamines and 5-Hydroxytryptamine Immobilized to Sepharose and Glass BeadsCanadian Journal of Physiology and Pharmacology, 1975
- Separation of Specific Antibody-Forming Mouse Cells by their Adherence to Insolubilized Endogenous HormonesJournal of Clinical Investigation, 1974
- Cyto-active amino-acid and peptide derivatives. Part I. Substituted phenylalaninesJournal of the Chemical Society, 1954