Formation of mononuclear and chloro-bridged binuclear copper(II) complexes of patellamide D, a naturally occurring cyclic peptide: influence of anion and solvent

Cyclic peptide marine metabolites and CuII

“…The observation that, despite the biotoxicity of Cu II , its concentration in the ascidians is roughly 10 4 times higher than in the surrounding sea water, has fostered the interest in the macromolecule's metal ion, and especially Cu II coordination chemistry. 34,[43][44][45][46][47][48][49][50][51][52][53][54][55][56][57][58][59] The focus of this perspective is on the Cu II coordination chemistry of the L. patella and L. bistratum cyclic peptides and a series of synthetic analogues. Structure and dynamics of the metal-free ligands and their applications are also reviewed.…”

New Methods for Medicinal Chemistry - Universal Gene Cloning and Expression Systems for Production of Marine Bioactive Metabolites

“…Sequencing the genome of Prochloron symbionts from a Palau specimen of L. patella, however, has revealed that the pathway is ribosomal [27]. Patellamide D, possibly as a binuclear copper complex [28], has additional pharmacological significance as a selective antagonist for reversing the multidrug resistant CEM/VLB100 human leukemic cell line towards vinblastine, colchicine and adriamycin treatment [29]. Potential clinical development of this pharmacophore is likely to be encouraged by achieving a sustainable supply of these bioactive marine metabolites.…”

Copper(II) Coordination Chemistry of Westiellamide and Its Imidazole, Oxazole, and Thiazole Analogues

“…[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19] The geometric arrangement of the functional groups and the size of the macrocycles suggest that their ) rings instead of oxazoline, is reported. As in the larger patellamide rings, the N heterocycle -N peptide -N heterocycle binding site is highly preorganized for copper(II) coordination.…”