In vitro effect of caffeic acid phenethyl ester on matrix metalloproteinases (MMP-1 and MMP-9) and their inhibitor (TIMP-1) in lipopolysaccharide-activated human monocytes

Vilela, Polyana das Graças Figueiredo; Oliveira, Jonatas Rafael de; Barros, Patrícia Pimentel de; Leão, Mariella Vieira Pereira; Oliveira, Luciane Dias de; Jorge, Antônio Olavo Cardoso

doi:10.1016/j.archoralbio.2015.04.009

Cited by 13 publications

(18 citation statements)

References 25 publications

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“…It inhibits lipid peroxidation and regulates antioxidant enzymes in the diabetic heart 105 . CAPE was able to inhibit the gene expression; production and the activity of matrix metalloproteinases induced by lipopolysaccharide and also increased the gene expression of human monocytic cell line 106 . At the molecular level, it modulates the activities of focal adhesion kinase 107 , inducible human immunodeficiency virus integrase 108 , nitric oxide synthase 109 , lipoxygenase 110 , and cyclooxygenase (COX) 111 .…”

Section: Resultsmentioning

confidence: 99%

The effect of caffeic acid phenethyl ester (CAPE) on metabolic enzymes including acetylcholinesterase, butyrylcholinesterase, glutathione S-transferase, lactoperoxidase, and carbonic anhydrase isoenzymes I, II, IX, and XII

Gülçın

Scozzafava

Supuran

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

160

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Health Services Vocational School, Igdır University, Igdır, Turkey AbstractCaffeic acid phenethyl ester (CAPE) is an active component of honeybee propolis extracts. Carbonic anhydrases (CAs, EC 4.2.1.1) are widespread and intensively studied metalloenzymes present in higher vertebrates including humans as many diverse isoforms. Acetylcholinesterase (AChE) is responsible for acetyl choline (ACh) hydrolysis and plays a fundamental role in nerve impulse transmission by terminating the action of the ACh neurotransmitter at cholinergic synapses and neuromuscular junctions. Butyrylcholinesterase (BChE) is another enzyme abundantly present in the liver and released into blood in a soluble form. Lactoperoxidase (LPO) is an enzyme involved in fighting pathogenic microorganisms whereas glutathione S-transferases (GSTs) are dimeric proteins present both in prokaryotic and eukaryotic organisms and involved in cellular detoxification mechanisms. In the present study, the inhibition effect of CAPE on human carbonic anhydrase (hCA) isoforms I, II, IX, and XII, AChE, BChE, LPO, and GST was evaluated. CAPE inhibited these enzymes with K i s in the range between micromolar to picomolar. The best inhibitory effect was observed against AChE and BChE.

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Section: Resultsmentioning

confidence: 99%

The effect of caffeic acid phenethyl ester (CAPE) on metabolic enzymes including acetylcholinesterase, butyrylcholinesterase, glutathione S-transferase, lactoperoxidase, and carbonic anhydrase isoenzymes I, II, IX, and XII

Gülçın

Scozzafava

Supuran

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

160

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“…is used to designate amino acid residues of a peptide substrate (Example of P1 group such as branched alkanes and cycloalkanes) [ 1 , 10 ]. Various reports have shown diazepine and caffeic acid (hydroxycinnamic acid) derivatives as the active moieties against MMPs [ 14 , 24 , 28 , 29 , 33 , 36 ]. Several modified caffeic acid amides have more steady features [ 25 ].…”

Section: Introductionmentioning

confidence: 99%

Targeting matrix metalloproteinases with novel diazepine substituted cinnamic acid derivatives: design, synthesis, in vitro and in silico studies

Rathee

Lather²,

Grewal

et al. 2018

Chemistry Central Journal

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Lung cancer is the notable cause of cancer associated deaths worldwide. Recent studies revealed that the expression of matrix metalloproteinases (MMPs) is extremely high in lung tumors compared with non-malignant lung tissue. MMPs (-2 and -9) play an important part in tumor development and angiogenesis, which suggests that creating potent MMP-2 and -9 inhibitors, should be an important goal in lung cancer therapy. In the present study, an effort has been made to develop new anti-metastatic and anti-invasive agents, wherein a series of novel diazepine substituted cinnamic acid derivatives were designed, synthesized and assayed for their inhibitory activities on MMP-2 and MMP-9. These derivatives were prepared via microwave assisted reaction of tert-butyl (3-cinnamamidopropyl)carbamate derivatives mixed with 2,3-dibromopropanoic acid and potassium carbonate was added to obtain 4-(tert-butoxycarbonyl)-1-cinnamoyl-1,4-diazepane-2-carboxylic acid derivatives. The newly synthesized compounds were characterized by IR, NMR and mass spectroscopy. All the tested compounds showed good to excellent cytotoxic potential against A549 human lung cancer cells. The active compounds displaying good activity were further examined for the inhibitory activity against MMPs (-2 and -9). In addition, the structure and anticancer activity relationship were further supported by in silico docking studies of the active compounds against MMP-2 and MMP-9.

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“…Under physiological conditions, the activity of MMPs is controlled by the tissue inhibitors of metalloproteinases (TIMPs) . Pathologically, increased levels of active MMPs and an imbalance between MMPs and TIMPs are associated with the progression of chronic inflammatory processes .…”

mentioning

confidence: 99%

“…Moreover, it has been demonstrated that TIMP‐1 is the main inhibitor of these MMPs in the periodontal tissues . Therefore, therapeutic agents that control the secretion and activation of MMPs and also regulate the balance between MMPs and TIMPs might be useful for the prevention and treatment of periodontitis .…”

mentioning

confidence: 99%

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Modulatory effect of curcumin analogs on the activation of metalloproteinases in human periodontal stem cells

Boșca¹,

Ilea

Şoriţău

et al. 2019

European J Oral Sciences

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Periodontitis progresses due to increased levels of active metalloproteinases (MMPs) and the imbalance between MMPs and their tissue inhibitors (TIMPs). Natural curcumin limits the lytic activity of MMPs but has low cellular uptake. Use of synthetic curcumin analogs could be a means of overcoming this limitation of treatment efficiency. Human periodontal stem cells were isolated from gingival tissue, gingival ligament fibers, periodontal ligament, and alveolar bone. The effect of five synthetic curcumin analogs was compared with that of natural curcumin by assessing cytotoxicity [by 3‐(4,5‐dimethylthiazol‐2yl)‐2,5‐diphenyltetrazolium bromide (MTT) assay], the cellular uptake (by fluorometry), the proteolytic activities of MMP‐2 and ‐9 (by zymography), and the levels of TIMP‐1 (by ELISA). Our results indicated increased cytotoxicity of synthetic curcumins for doses between 100 and 250 μM. At a concentration of 10 μM, cellular uptake of synthetic curcumins varied depending on their chemical structure. The curcumin compounds modulated pro‐MMP‐2 levels and increased TIMP‐1 production. There was no detectable synthesis of pro‐MMP‐9 and no activation of MMPs 2 and 9. Gingival tissue and gingival ligament fiber stem cells were most responsive to treatment, showing inverse correlations between pro‐MMP‐2 and TIMP‐1 levels. In conclusion, synthetic curcumins influenced the balance between pro‐MMP‐2 and TIMP‐1 in human periodontal stem cells in vitro, and this could open perspectives for their application as adjuvants in periodontal therapy.

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In vitro effect of caffeic acid phenethyl ester on matrix metalloproteinases (MMP-1 and MMP-9) and their inhibitor (TIMP-1) in lipopolysaccharide-activated human monocytes

Cited by 13 publications

References 25 publications

The effect of caffeic acid phenethyl ester (CAPE) on metabolic enzymes including acetylcholinesterase, butyrylcholinesterase, glutathione S-transferase, lactoperoxidase, and carbonic anhydrase isoenzymes I, II, IX, and XII

The effect of caffeic acid phenethyl ester (CAPE) on metabolic enzymes including acetylcholinesterase, butyrylcholinesterase, glutathione S-transferase, lactoperoxidase, and carbonic anhydrase isoenzymes I, II, IX, and XII

Targeting matrix metalloproteinases with novel diazepine substituted cinnamic acid derivatives: design, synthesis, in vitro and in silico studies

Modulatory effect of curcumin analogs on the activation of metalloproteinases in human periodontal stem cells

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