Molecular mechanism depressing PMA-induced invasive behaviors in human lung adenocarcinoma cells by cis- and trans-cinnamic acid

Tsai, Chia‐Jung; Sun, Fang-Ming; Chen, Yen-Ling; Hsu, Chin-Lin; Yen, Gow‐Chin; Weng, Chia‐Jui

doi:10.1016/j.ejps.2012.11.013

Cited by 29 publications

(21 citation statements)

References 46 publications

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“…The activity of NF-κB is driven by the level of its inhibitor IκB and by the activity of several mitogen-activated protein kinases (MAPKs), especially p38 and c-Jun N-terminal kinase (JNK) [35,36], as well as ERK [37]. The influence of CA on NF-κB and MAPKs expression and activity was described previously [38,39], the same as for some cinnamides [23]. Our results showed no effect of compounds 17, 8, and CA on the IκBα levels and MAPKs activity, see Figure 6.…”

Section: Nf-b Activity [% Of Dmso]mentioning

confidence: 99%

Investigation of Anti-Inflammatory Potential of N-Arylcinnamamide Derivatives

et al. 2019

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A series of sixteen ring-substituted N-arylcinnamanilides, previously described as highly antimicrobially effective against a wide spectrum of bacteria and fungi, together with two new derivatives from this group were prepared and characterized. Moreover, the molecular structure of (2E)-N-(2-bromo-5-fluorophenyl)-3-phenylprop-2-enamide as a model compound was determined using single-crystal X-ray analysis. All the compounds were tested for their anti-inflammatory potential, and most tested compounds significantly attenuated the lipopolysaccharide-induced NF-κB activation and were more potent than the parental cinnamic acid. (2E)-N-[2-Chloro-5-(trifluoromethyl)phenyl]-3-phenylprop-2-enamide, (2E)-N-(2,6-dibromophenyl)-3-phenylprop-2-enamide, and (2E)-N-(2,5-dichlorophenyl)-3-phenylprop-2-enamide demonstrated the highest inhibition effect on transcription factor NF-κB at the concentration of 2 µM and showed a similar effectiveness as the reference drug prednisone. Several compounds also decreased the level of TNF-α. Nevertheless, subsequent tests showed that the investigated compounds affect neither IκBα level nor MAPKs activity, which suggests that the N-arylcinnamanilides may have a different mode of action to prednisone. The modification of the C (2,5) or C (2,6) positions of the anilide core by rather lipophilic and bulky moieties seems to be preferable for the anti-inflammatory potential of these compounds.Molecules 2019, 24, 4531 2 of 15 drugs are directly obtained from plants or fungi or are "nature-inspired" [11]. One such molecule is cinnamic acid (CA). It is a small organic molecule, which can be found in many kinds of plants in pure form or as a part of more complicated structures. CA and its natural and synthetic derivatives possess many interesting biological effects, such as antimicrobial [12,13], anticancer [14], anti-oxidant [13], and anti-inflammatory activities [15].N-Arylcinnamides represent a group of synthetic derivatives of CA. This group of compounds possesses several potentially active moieties-styryl, amide (peptide-like [16]) bond, and aryl [17][18][19][20][21][22]. Thus, cinnamides can be considered as a privilege structure or a scaffold (a part) of more complex molecules in medicinal chemistry [23,24] The series of N-arylcinnamide derivatives presented in this work was previously tested for their anti-microbial activity (compounds 1-15 and 17) [25,26], and three new derivatives 16 and 18 were prepared and characterized. Based on the concepts of polypharmacology, multifactorial diseases, and multitarget drugs [27], as well as the above-mentioned results, a group of eighteen N-arylcinnamanilides was chosen for the screening of their ability to moderate the inflammation-like reaction in vitro. Results and Discussion ChemistryThe investigated compounds (previously published compounds 1-15 and 17 [25] and two new compounds, 16 and 18) were prepared using a one-step microwave-assisted synthesis, see Scheme 1. Briefly, the carboxyl group of CA was activated with phosphorus trichloride, and then...

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Section: Nf-b Activity [% Of Dmso]mentioning

confidence: 99%

Investigation of Anti-Inflammatory Potential of N-Arylcinnamamide Derivatives

et al. 2019

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“…Cinnamic acid is a white oily phenolic powder found in many dietary plants, fruits, and herbs (He et al, 2005;Tsai et al, 2013;Zhang et al, 2013). Cinnamic acid (1 ng/mL) isolated from Cinnamomum cassia activates insulin-mediated glucose transport through the involvement of GLUT4, but via a PI3K-independent pathway, in L6 myotubes (Lakshmi et al, 2009).…”

Section: Cinnamic Acidmentioning

confidence: 99%

Antidiabetic Effects of Simple Phenolic Acids: A Comprehensive Review

2015

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Diabetes mellitus (DM) has become a major public health threat across the globe. Current antidiabetic therapies are based on synthetic drugs that very often have side effects. It has been widely acknowledged that diet plays an important role in the management of diabetes. Phenolic acids are widely found in daily foods such as fruits, vegetables, cereals, legumes, and wine and they provide biological, medicinal, and health properties. Simple phenolic acids have been shown to increase glucose uptake and glycogen synthesis, improve glucose and lipid profiles of certain diseases (obesity, cardiovascular diseases, DM, and its complication). The current review is an attempt to list out the antidiabetic effects of simple phenolic acids from medicinal plants and botanical foods.

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“…Trans-cinnamic acid (t-CA), 3-Phenyl-2propenoic acid, is a white oily phenolic powder found in many dietary plants, fruits, and herbs [He et al, 2005;Tsai et al, 2013;Zhang et al, 2013]. Cinnamomum cassia or Chinese cinnamon is the main source of t-CA.…”

Section: Introductionmentioning

confidence: 99%

Self‐Nanoemulsifying Drug Delivery System of trans‐Cinnamic acid: Formulation Development and Pharmacodynamic Evaluation in Alloxan‐induced Type 2 Diabetic Rat Model

Wang

Deng

et al. 2015

Drug Development Research

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The objective of this study was to formulate a self-nanoemulsifying oral drug delivery system (SNEDDS) for the poorly water-soluble trans-Cinnamic acid (t-CA SNEDDS) that could be evaluated for its antihyperglycemic efficacy in comparison to the parent t-CA in an alloxan-induced diabetic rat model. A SNEDDS formulation consisting of 60% surfactant (Kolliphor EL), 10% co-surfactant (PEG 400) and 30% oil (isopropyl myristate) proved to be optimal. t-CA SNEDDS (80 mg/kg, p.o.), t-CA suspension (80 mg/kg, p.o.), and Metformin Hydrochloride Tablets (230 mg/kg, p.o.) were administer qdfor 30 days to diabetic rats. After treatment the body weight of diabetic rats was increased, blood glucose levels, total cholesterol, and triglyceride in the serum tended to be normalized, while the levels of alanine aminotransferase and aspartate aminotransferase were markedly decreased. The effects of t-CA SNEDDS were superior to that of the t-CA suspension. The present study demonstrated that t-CA was effective in attenuating the effects of alloxan treatment and that t-CA SNEDDS with a more favorable absorption and enhanced bioavailability is more effective than t-CA.

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Molecular mechanism depressing PMA-induced invasive behaviors in human lung adenocarcinoma cells by cis- and trans-cinnamic acid

Cited by 29 publications

References 46 publications

Investigation of Anti-Inflammatory Potential of N-Arylcinnamamide Derivatives

Investigation of Anti-Inflammatory Potential of N-Arylcinnamamide Derivatives

Antidiabetic Effects of Simple Phenolic Acids: A Comprehensive Review

Self‐Nanoemulsifying Drug Delivery System of trans‐Cinnamic acid: Formulation Development and Pharmacodynamic Evaluation in Alloxan‐induced Type 2 Diabetic Rat Model

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