Anthranilic acid derivatives: a new class of non-peptide CCK1 receptor antagonists

Varnavas, Antonio; Lassiani, Lucia; Valenta, Valentina; Berti, Federico; Mennuni, Laura; Makovec, Francesco

doi:10.1016/s0968-0896(02)00475-3

Cited by 20 publications

(20 citation statements)

References 30 publications

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“…Such compounds possess defensive functions (Kanias et al, 1992). Indole-5-carboxylic acid and dehydroabietic acid are unusual for marine organisms and might have some defensive functions or have some control function in metabolism (Takami et al, 1998;Varnavas et al, 2003). These compounds might be used as taxonomic markers for H. sanguinea.…”

Section: Canary Islandsmentioning

confidence: 99%

Chemical composition of the sponge Hymeniacidon sanguinea from the Canary Islands

Nechev

Christie²,

Robaina

et al. 2004

Comparative Biochemistry and Physiology Part A: Molecular &

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The fatty acid composition of the lipids from the sponge Hymeniacidon sanguinea was investigated and 73 acids were identified. Three of them were new and their structures, elucidated by gas chromatographyymass spectrometry, were identified as 13-methyl-icosanoic, 15-methyl-docosanoic and 3,13-dimethyl-tetradecanoic. Only 12 sterols were present, with cholestanol predominating in the volatile fraction; 22 compounds were identified, mainly hydrocarbons and fatty acids. In the n-butanol fraction, we found mainly nitrogen-containing compounds. The compositions of sterols and lipids in the sponge collected from two locations with different ecological conditions (Canary Islands and Black Sea) were compared. ᮊ

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Section: Canary Islandsmentioning

confidence: 99%

Chemical composition of the sponge Hymeniacidon sanguinea from the Canary Islands

Nechev

Christie²,

Robaina

et al. 2004

Comparative Biochemistry and Physiology Part A: Molecular &

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“…Cyclopeptides with an anthranilic acid unit are rare in nature. Two antifungal cyclopeptides with an anthranilic acid unit, sclerotides A and B, were isolated from the marine-derived Aspergillus sclerotiorum PT06-1 in a nutrient-limited hypersaline cultural medium [11]. Anthranilic acid dimers with micromolar affinity for the CCK1 receptors were considered to be an important molecular scaffold in medicinal chemistry [12].…”

Section: Introductionmentioning

confidence: 99%

Two Novel Hepatocellular Carcinoma Cycle Inhibitory Cyclodepsipeptides from a Hydrothermal Vent Crab-Associated Fungus Aspergillus clavatus C2WU

Jiang

Chen

et al. 2013

Marine Drugs

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Two novel cyclodepsipeptides containing an unusual anthranilic acid dimer and a d-phenyllactic acid residues, clavatustides A (1) and B (2), were identified from cultured mycelia and broth of Aspergillus clavatus C2WU isolated from Xenograpsus testudinatus, which lives at extreme, toxic habitat around the sulphur-rich hydrothermal vents in Taiwan Kueishantao. This is the first example of cyclopeptides containing an anthranilic acid dimer in natural products, and the first report of microbial secondary metabolites from the hydrothermal vent crab. Clavatustides A (1) and B (2) suppressed the proliferation of hepatocellular carcinoma (HCC) cell lines (HepG2, SMMC-7721 and Bel-7402) in a dose-dependent manner, and induced an accumulation of HepG2 cells in G1 phase and reduction of cells in S phase.

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“…Attempts to simplify these compounds resulted in monomeric anthranilic acid derivatives, such as compound 25 (VL-0395), Fig. (4), endowed with submicromolar affinity towards CCK1R and a quite good selectivity [53,54]. The antagonist nature of this compound was confirmed by the inhibition of the guinea pig gallbladder contraction induced by CCK-8 in vivo, with a potency (ED 50 = 0.38 μmol/kg) similar to that exhibited by loxiglumide in the same assay.…”

Section: Anthranilic Acid Derivativesmentioning

confidence: 99%

Strategies for Design of Non Peptide CCK1R Agonist/Antagonist Ligands

García-López¹,

González‐Muñiz²,

Martı́n-Martı́nez³

et al. 2007

CTMC

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This review mainly covers last five year literature on CCK1R agonists and antagonists. These CCK1R ligands have been found following the two usual and complementary strategies for drug discovery: rational design based on structure activity relationships on the CCK-7 and CCK-4 peptide sequences of the endogenous ligands and random screening of diverse compounds, followed by hit optimization. The first group includes: chimeric bifunctional opioid/CCK peptides, designed as opioid agonists with balanced CCK1R/CCK2R antagonist activity for the treatment of neuropathic pain, antagonist and agonist dipeptoids, and 1,3-dioxoperhydropyrido[1,2-c]pyrimidine- and anthranilic acid-based antagonists. Among the ligands derived from random screening, a few new 1,4-benzodiazepine-, 1,5-benzodiazepine-, and five member ring heterocycle-based CCK1R ligands have been reported. Finally, taking into account the importance of receptor mapping studies for ligand optimization and future precise de novo receptor structure-based design of new selective and more effective ligands, the most significant conclusions of these studies have also been reviewed.

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Anthranilic acid derivatives: a new class of non-peptide CCK1 receptor antagonists

Cited by 20 publications

References 30 publications

Chemical composition of the sponge Hymeniacidon sanguinea from the Canary Islands

Chemical composition of the sponge Hymeniacidon sanguinea from the Canary Islands

Two Novel Hepatocellular Carcinoma Cycle Inhibitory Cyclodepsipeptides from a Hydrothermal Vent Crab-Associated Fungus Aspergillus clavatus C2WU

Strategies for Design of Non Peptide CCK1R Agonist/Antagonist Ligands

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