Synthesis of a novel class of fatty acids-derived isoquinolines

Matuszewska, Iwona; Leniewski, Andrzej; Roszkowski, Piotr; Czarnocki, Zbigniew

doi:10.1016/j.chemphyslip.2005.02.008

Cited by 9 publications

(4 citation statements)

References 24 publications

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“…Dodecanal and farnesol were purchased from commercial sources and used without further purification. Hexanal [60], undecanal [61], tridecanal [62], octadecanal [63], and 2,5,8,11-tetraoxatridecan-13-al [64] all were obtained by oxidation of the corresponding primary alcohol and exhibited characterization consistent with the published literature. Final purity assessments were made based on an analytical RP-HPLC-MS system from Agilent Technologies Inc. (Santa Clara, CA, USA) using the following columns and conditions: Phenomenex Synergi Polar-RP (Phenomenex, Torrance, CA, USA), 4,6 mm × 150 mm, 4 µm, UV detection (Agilent Technologies Inc., Santa Clara, CA, USA) at 250 nm or 280 nm, 5–50% MeCN with 0.1% formic acid (FA) in water (0.1% FA) over 20 min at 0.5 mL/min, or 30–90% MeOH (0.1% FA) in water (0.1% FA) over 20 min at 0.5 mL/min; Phenomenex C18 4.6 mm × 50 mm, 4 µM, UV detection at 280 nm, 10–90% MeCN (0.1% FA) in water (0.1% FA) over 15 min at 0.5 mL/min, or 10–90% MeOH (0.1% FA) in water (0.1% FA) over 15 min at 0.5 mL/min.…”

Section: Methodssupporting

confidence: 54%

Application of N-Dodecyl l-Peptide to Enhance Serum Stability while Maintaining Inhibitory Effects on Myometrial Contractions Ex Vivo

et al. 2019

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N-Alkylation and N-acylation of the prostaglandin-F2α allosteric modulator l-PDC31 were performed to install various alkyl, PEG and isoprenoid groups onto the l-enantiomer of the peptide. Among the different bio-conjugates studied, the N-dodecyl analog reduced prostaglandin-F2α-induced mouse myometrium contractions ex vivo. Furthermore, N-dodecyl-l-PDC31 exhibited improved stability in a mouse serum assay, likely due to protection from protease degradation by the lipid chain.

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Section: Methodssupporting

confidence: 54%

Application of N-Dodecyl l-Peptide to Enhance Serum Stability while Maintaining Inhibitory Effects on Myometrial Contractions Ex Vivo

et al. 2019

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“…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%

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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“…In 2014, palmitoyl esters of green-tea polyphenols (GTP) were approved for food use in China with the maximum-tolerated dose of 600 mg kg –1 . Lipophenols can also be used as novel functional ingredients for food products, because of the biological properties and positive effects on health due to their interactions with the endocannabinoid system − and inhibition of enzyme activity, − as well as their antioxidant, anti-carbonyl-stress, ,− anti-inflammatory, − antibacterial, and antiparasitic activities. ,− …”

Section: Introductionmentioning

confidence: 99%

Hydrolysis and Transport Characteristics of Tyrosol Acyl Esters in Rat Intestine

Yin

Zhou

et al. 2018

J. Agric. Food Chem.

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Lipophenols such as palmitoyl esters of green-tea polyphenols (GTP) have been allowed for use as food additives for oxidation control. However, their digestive absorption remains unexplored. In this paper, the hydrolysis and transport characteristics of tyrosol acyl esters (TYr-Es) with various fatty acids (C12:0, C14:0, C16:0, C18:0, C18:1, and C18:2) were evaluated using the everted-rat-gut-sac model for the first time. HPLC-UV measurements demonstrated that TYr-Es were hydrolyzed to TYr, which contributed significantly to TYr transport across the sacs. The hydrolysis and transport rates correlated negatively with the chain lengths of their lipid moieties but showed a positive correlation with the degree of unsaturation. In general, all TYr-Es exhibited sustained-release behavior; therefore, the production of TYr-Es may serve as a useful way to prolong the duration of action and further improve the bioactivities of TYr.

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Synthesis of a novel class of fatty acids-derived isoquinolines

Cited by 9 publications

References 24 publications

Application of N-Dodecyl l-Peptide to Enhance Serum Stability while Maintaining Inhibitory Effects on Myometrial Contractions Ex Vivo

Application of N-Dodecyl l-Peptide to Enhance Serum Stability while Maintaining Inhibitory Effects on Myometrial Contractions Ex Vivo

Omega-3 polyunsaturated lipophenols, how and why?

Hydrolysis and Transport Characteristics of Tyrosol Acyl Esters in Rat Intestine

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