Acylamido analogs of endocannabinoids selectively inhibit cancer cell proliferation

Bioorganic & Medicinal Chemistry
2008.0

Abstract

A series of amide derivatives of long-chain fatty acids has been studied for their effects on the proliferation of cancer cells in vitro. Fatty acids ranged from palmitic to higher polyunsaturated types containing 22 carbon atoms. The amino portions of the molecules included ammonia, ethanolamine, various amino acids and dopamine. Several cell lines were used as models and these included HTB-125 (normal human breast cells), HTB-126 (human breast cancer cells), HeLa (cervical cancer cells), WI-38 (human embryonic lung cells), RAW264.7 (mouse macrophage tumor cells) and RBL-2H3 (rat basophilic leukemia cells). The HTB lines were obtained from the same donor, so, could be considered a matched pair, that is, normal control versus cancer cells and thus, provide a model for testing specificity of action for the acylamido analogs. While many compounds were efficacious in inhibiting the proliferation of various cell lines, only two analogs showed a high degree of specificity in the matched HTB cell lines. N-palmitoyl dopamine and N-palmitoyl tyrosine each demonstrated complete specificity of action at a concentration of 10muM and were highly efficacious in both cases. No clear structure-activity pattern could be derived from these studies since the intensity of the inhibitory action seemed to depend on three factors, namely, the fatty acid, the amine group and the cell type.

Knowledge Graph

Similar Paper

Acylamido analogs of endocannabinoids selectively inhibit cancer cell proliferation
Bioorganic & Medicinal Chemistry 2008.0
Antiproliferative activity of synthetic fatty acid amides from renewable resources
Bioorganic & Medicinal Chemistry 2015.0
Evaluation of endogenous fatty acid amides and their synthetic analogues as potential anti-inflammatory leads
Bioorganic & Medicinal Chemistry 2011.0
Fatty acyl amide derivatives of doxorubicin: Synthesis and in vitro anticancer activities
European Journal of Medicinal Chemistry 2011.0
Synthesis and biological evaluation of novel amides of polyunsaturated fatty acids with dopamine
Bioorganic & Medicinal Chemistry Letters 2001.0
Structure−Activity Relationships on Phenylalanine-Containing Inhibitors of Histone Deacetylase:  In Vitro Enzyme Inhibition, Induction of Differentiation, and Inhibition of Proliferation in Friend Leukemic Cells
Journal of Medicinal Chemistry 2002.0
Hederagenin amide derivatives as potential antiproliferative agents
European Journal of Medicinal Chemistry 2019.0
Antiproliferative activity and mode of action analysis of novel amino and amido substituted phenantrene and naphtho[2,1-b]thiophene derivatives
European Journal of Medicinal Chemistry 2020.0
2-Cinnamamido, 2-(3-phenylpropiolamido), and 2-(3-phenylpropanamido)benzamides: Synthesis, antiproliferative activity, and mechanism of action
European Journal of Medicinal Chemistry 2013.0
Identification of Sansalvamide a analog potent against pancreatic cancer cell lines
Bioorganic & Medicinal Chemistry Letters 2007.0