Evaluation of endogenous fatty acid amides and their synthetic analogues as potential anti-inflammatory leads

Dang, Hung; Kang, Gyeoung Jin; Yoo, Eun Sook; Hong, Jongki; Choi, Jae Sue; Kim, Hyung Sik; Chung, Hae Young; Jung, Jee H.

doi:10.1016/j.bmc.2010.12.046

Cited by 41 publications

(26 citation statements)

References 33 publications

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“…Inspired by the discovery of C22 enone FA (EFOX, electrophilic oxo derivatives), DHA and DPA metabolites generated during inflammation process by COX-2, Dang et al [29], compared the anti-inflammatory activity of a wide range of N-acyl FAs (saturated FA and PUFA) including N-acyl-dopamine 12, N-acyl vanillylamine 11, and their enone fatty acid analogues. N-acyl dopamine conjugates exhibited the most potent inhibitory activity on the production of NO, cytokines IL-1b, IL-6 and TNF-a, in LPS-activated RAW264.7.…”

Section: Anti-inflammatory Activitymentioning

confidence: 99%

“…At the difference with ester or amide linkages between the phenolic compound and the PUFA part, non hydrolysable bounds have been obtained [38] [18][19]29] (dopamine and analogues) 11 [26,29,67] (vanillyl amine) 14 [17] ( [28] (Farinosone C analogue) 21 [20] (juglone) 22 [23] (shikonin) Dox-hyd-PUFA: 24a Dox-3-ami-PUFA: 24b (doxorubicin) [25,[63][64][65] 23 [27] (podophyllotoxin analogue) DDPT 15 [37] (phloroglucinol) 4'-PUFA:17a [22,37] 3-DHA: 17b (resveratrol) 18 [21] (trimethoxy anilide) 19 [24,66] (diisopropylphenol) 3 5 4' 3 3 2 [34][35] (EGC) 3 [36] (quercetin) 4 [15] (naringin) 5 [10][11][13][14][15] (rutin) 6 [12] (phloridzin) 7 [12] (isoquercitrin) 8 [38] 9 [30] 10 [ linker [39]. Since pH in tumor cells is lower than in healthy tissue, the hydrazone bond, stable at pH 7.4, is rapidly cleaved at lower pH in cancerous cells.…”

Section: Chemical Synthesismentioning

confidence: 99%

“…The introduction of a PUFA moiety onto chemical structures having a single free phenolic function (juglone 21, propofol 19, podophyllotoxin derivatives 23), or one amino or aliphatic-alcohol group, with higher nucleophilicity than the phenolic one (dopamine and analogues 12, trimethoxy anilide 18, farinosone C 20, shikonin 22), was performed either by the well-established esterification procedure using either the proper preformed mixed anhydrides [18,19] or acyl chlorides [20e22] of the PUFA, or a classical coupling reagent, such as, DCC/DMAP [23e27], pentafluorophenol/ TEA [28], TBTU/TEA [29] or TCTU/TEA [30]. Whatever the used procedure and reagents, moderate to good yields were obtained.…”

Section: Chemical Synthesismentioning

confidence: 99%

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Omega-3 polyunsaturated lipophenols, how and why?

et al. 2016

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Polyphenols and n-3 polyunsaturated fatty acids (PUFAs) are two classes of natural compounds, which have been highlighted in epidemiological studies for their health benefits. The biological activities of those two families of metabolites on oxidation, inflammation, cancer, cardiovascular and degenerative diseases have been reported in vitro and in vivo. On the other hand, chemical bonding between the two structures leading to n-3 lipophenol derivatives (or phenolipids) has been studied in numerous works over the last decade, and some examples could also be found from natural sources. Interest in lipophilization of phenolic structures is various and depends on the domain of interest: in food industry, the development of lipidic antioxidants could be performed to protect lipidic food matrix from oxidation. Whereas, on pharmaceutical purpose, increasing the lipophilicity of polar phenolic drugs could be performed to improve their pharmacological profile. Moreover, combining both therapeutic aspects of n-3 PUFAs and of polyphenols in a single lipophenolic molecule could also be envisaged. An overview of the synthesis and of the natural sources of n-3 lipophenols is presented here, in addition to their biological activities which point out in several cases the benefit of the conjugated derivatives.

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Section: Anti-inflammatory Activitymentioning

confidence: 99%

Section: Chemical Synthesismentioning

confidence: 99%

Section: Chemical Synthesismentioning

confidence: 99%

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Omega-3 polyunsaturated lipophenols, how and why?

et al. 2016

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“…N-Oleoyl dopamine, a commercially available compound with biomedical research interest [25][26][27] was synthesized via the amidation of oleoyl chloride.…”

Section: Synthesis Of Oleoyldopaminementioning

confidence: 99%

Myoblast Cell Interaction with Polydopamine Coated Liposomes

et al. 2012

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Liposomes are widely used, from biosensing to drug delivery. Their coating with polymers for stability and functionalization purposes further broadens their set of relevant properties. Poly(dopamine) (PDA), a eumelanin-like material deposited via the “self”-oxidative polymerization of dopamine at mildly basic pH, has attracted considerable interest in the past few years due to its simplicity, flexibility yet fascinating properties. Herein, we characterize the coating of different types of liposomes with PDA depending on the presence of oleoyldopamine in the lipid bilayer and the dopamine hydrochloride concentration. Further, the interaction of these coated liposomes in comparison to their uncoated counterparts with myoblast cells is assessed. Their uptake/association efficiency with these cells is determined. Further, their dose-dependent cytotoxicity with and without entrapped hydrophobic cargo (thiocoraline) is characterized. Taken together, the reported results demonstrate the potential of PDA coated liposomes as a tool in biomedical applications. Supplementary Material 13758_2011_8_MOESM1_ESM.doc (83KB)

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“…The authors reported that both compounds inhibited locomotion and induced catalepsy, hypothermia and analgesia in rats, demonstrating their ability to produce cannabinoid-like effects in vivo via CB 1 [28]. Moreover, it has been reported that some N-acyl-dopamines are able to exert positive effects on hypoxic-ischaemic injury or brain inflammatory processes and to inhibit cancer cell proliferation [29,30], suggesting N-acyldopamines as potential antiinflammatory and antitumor leads.…”

Section: Accepted Manuscriptmentioning

confidence: 96%