- Mechanism of high thermal stability of commercial polyesters and polyethers conjugated with bio-based caffeic acid
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In previous report, we discovered that a novel improvement technique to enhance the thermal properties of poly(L-lactide)s (PLLAs) by terminal conjugation with 3,4-diacetoxycinnamic acid (DACA). In this study, we clarified the mechanism of the enhancement of thermal stability by using commercial polyesters and polyethers. The effect of thermal improvement by the terminal conjugation of DACA on poly(DL-lactide), poly(ε-caprolactone), and poly(ethylene glycol) was almost the same as about 100 °C increase. The amount of residual tin catalyst, which enhances the thermal degradation of polyesters, was reduced at undetected level after the terminal conjugation of DACA probably due to the removal of tin during DACA conjugation process. Furthermore, the π-π stacking interactions of DACA units and the chemical protection of terminal hydroxyl groups, which enhances intramolecular scission, were also important for the high thermal stability. We clarified that the extreme high thermal stability by DACA conjugation was induced by these above mechanisms.
- Thi, Tran Hang,Matsusaki, Michiya,Hirano, Hiroshi,Kawano, Hiroaki,Agari, Yasuyuki,Akashi, Mitsuru
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- A stereocomplex of poly(lactide)s with chain end modification: Simultaneous resistances to melting and thermal decomposition
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The simultaneous improvement of the melting temperature (Tm = 224 °C) and the decomposition temperature (T10 = 359 °C) of poly(lactide)s was achieved by the stereocomplex formation of poly(l-lactide) and poly(d-lactide) with bio-based aromatic groups at both initiating and terminating chain ends.
- Ajiro, Hiroharu,Hsiao, Yi-Ju,Thi, Tran Hang,Fujiwara, Tomoko,Akashi, Mitsuru
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- Synthetic phenylethanoid glycoside derivatives as potent neuroprotective agents
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Several phenylethanoid glycoside derivatives were designed and synthesized. Most of the synthetic compounds showed significant neuroprotective effects, including antioxidative and anti-apoptotic properties. Specifically, target compounds displayed potent effects against various toxicities such as H2O2 and 6-hydroxydopamine (6-OHDA) in PC12 cells. Among the synthetic derivatives, three compounds (5, 6, 8) exhibited much superior activities to the marketed drug Edaravone. The compounds were able to prevent the 6-OHDA-induced damage in PC12 cells in a dose-dependent manner. The anti-apoptotic effects could be observed via cell morphological changes. Moreover, the compounds significantly reduced the intracellular ROS increase resulting from 6-OHDA treatment. The preliminary structure-activity relationships were also explored. Compounds 5, 6, 8 may hold the potential as promising neuroprotective agents and new lead compounds for the treatment of neurodegenerative diseases or cerebral ischemia.
- Liu, Ying-Guo,Li, Xiaxi,Xiong, De-Cai,Yu, Binhan,Pu, Xiaoping,Ye, Xin-Shan
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- Polymerization of the triphosphates of AraC, 2',2'-difluorodeoxycytidine (dFdC) and OSI-7836 (T-araC) by human DNA polymerase alpha and DNA primase.
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OSI-7836 (4'-thio-araC, T-araC) is a nucleoside analogue that shows efficacy against solid tumor xenograft models. We examined how the triphosphates of OSI-7836 (T-araCTP), cytarabine (araCTP), and gemcitabine (dFdCTP) affected the initiation of new DNA strands by the pol alpha primase complex. Whereas dFdCTP very weakly inhibited primase, both T-araCTP and araCTP potently inhibited this enzyme. Primase polymerized T-araCTP and araCTP more readily than its natural substrate, CTP, and incorporation resulted in strong chain termination. dFdCTP, araCTP, and T-araCTP inhibited pol alpha competitively with respect to dCTP. When exogenously added primentemplates were used, pol alpha incorporated all three analogues into DNA, and incorporation caused either weak chain termination (dFdCTP), strong termination (araCTP), or extremely strong termination (T-araC). Furthermore, pol alpha polymerized T-araCTP only nine-fold less well than dCTP, whereas it polymerized araCTP and dFdCTP 24- and 83-fold less well, respectively. The presence of these three analogues in the template strand resulted in significant pausing by pol alpha, although the site and severity of pausing varied between the analogues. During the elongation of primase-synthesized primers, a reaction that is thought to mimic the normal sequence of events during the initiation of new DNA strands, pol alpha polymerized all three compounds. However, incorporation of araCTP and dFdCTP resulted in minimal chain termination, while incorporation of T-araCTP still caused extremely strong termination. The implications of these results with respect to how these compounds affect cells are discussed.
- Shin, Kyung-Min,Kim, In-Tae,Park, Youg-Mi,Ha, Joohun,Choi, Jong-Won,Park, Hee-Juhn,Lee, Yong Sup,Lee, Kyung-Tae
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- Thermally stable and photoreactive polylactides by the terminal conjugation of bio-based caffeic acid
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Caffeic acid terminally conjugated with polylactide showed high thermal stability and photoreactivity, and may be useful as a functional polylactide in the environmental and medical fields. The Royal Society of Chemistry.
- Hang Thi, Tran,Matsusaki, Michiya,Akashi, Mitsuru
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- Synthesis of cinnamoyl ketoamides as hybrid structures of antioxidants and calpain inhibitors
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The excessive calpain activation causes serious cellular damage or even cell death in neurological disorders such as stroke and Alzheimer's disease. Oxidative stress has also been implicated in the initiation or progression of neurodegenerative diseases. In the present studies, a series of cinnamoyl ketoamides 4a-4j were synthesized as hybrid structures of antioxidants and calpain inhibitors. Cinnamoyl ketoamides, possessing an alkyl chain at the α-position, showed potent μ-calpain inhibitory activities indicating that the cinnamoyl skeleton can be regarded as an acyclic variant of calpain inhibitory chromone carboxamide 2. Among synthesized, compound 4e was the most potent inhibitor of μ-calpain (IC50 = 0.13 μM) and also exhibited strong antioxidant activities in DPPH and superoxide anion radical scavenging and lipid peroxidation inhibition assay systems.
- Yoo, Yeong Jae,Nam, Dong Hyuk,Jung, Seo Yun,Jang, Jae Wan,Kim, Hyoung Ja,Jin, Changbae,Pae, Ae Nim,Lee, Yong Sup
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- Synthesis of caffeic acid sulfonamide derivatives and their protective effect against H2O2 induced oxidative damage in A549 cells
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Exogenous antioxidants are considered as important therapeutic tools for oxidative stress associated disorders as they can regulate the redox state, which is associated with cell and organ function. Inspired by natural polyphenols, six new caffeic acid sulfonamide derivatives were synthesized by coupling sulfonamides to the backbone of caffeic acid with good yields. Their structure and lipophilicity were characterized by 1H nuclear magnetic resonance (NMR), 13C{1H} NMR, infrared spectroscopy (IR) and oil-water partition coefficient assay. Their free radical scavenging activity and antioxidant activity were assessed by DPPH assay and hydrogen peroxide (H2O2) induced oxidative stress in human lung carcinoma A549 cells. The oil-water partition coefficient results indicate that the conjugation of sulfonamides increases the lipophilicity of caffeic acid. The CASMD, CASDZ and CASN results show higher free radical scavenging effects compared with vitamin C. The derivatives do not show any inhibitory effect on the proliferation of A549 cells up to a concentration of 200 μM, except CASDZ which significantly inhibits the growth of A549 cells at a concentration of 200 μM. In addition, the obtained derivatives markedly attenuate H2O2 induced decrease of cell viability, inhibit the production of ROS and MDA, and promote the activities of superoxide dismutase (SOD), catalase (CAT) and glutathione peroxidase (GSH-Px). Besides, treatment of H2O2 stimulated A549 cells with caffeic acid sulfonamide derivatives further increases mRNA expression of NF-E2-related factor 2 (Nrf2) and its target genes, including heme oxygenase-1 (HO-1), NAD(P)H quinone dehydrogenase 1 (NQO1) and thioredoxin reductase 1 (TXNRD1). These results suggest that these new caffeic acid sulfonamide derivatives have higher lipophilicity and better antioxidant activities than the parent caffeic acid, and they might be able to control the antioxidant response in cells via the Nrf2 pathway.
- Chen, Hailan,Hu, Tingjun,Lin, Cuiwu,Natarajan, Bharathi,Peng, Xiaoyu,Wei, Jiata,Yan, Hao,Zhang, Yuxue,Zhao, Anran
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- Novel 3C-like protease inhibitor as well as preparation method and application thereof
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The invention provides a novel 3C-like protease inhibitor which is 3 ", 4" - O - diacetyl -epicatechin trans-caffeic acid ester with a specific structure. The invention further provides a preparation method and application of the 3C-like protease inhibitor. The invention has the advantages that the compound 3 ", 4" - O - diacetyl - epicatechin trans-caffeic acid ester is designed and synthesized based on the structure of epicatechin; even when the concentration is low, the activity of 3C-like protease in the novel coronavirus can be obviously inhibited. The compounds can be used as 3C-like protease inhibitors and are used for preparing anti-novel coronavirus SARS-CoV - 2 infection drugs.
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Paragraph 0047-0048; 0057-0059
(2021/09/26)
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- ORAL PHARMACEUTICAL FORMULATIONS OF BITTER COMPOUNDS FOR PULMONARY HYPERTENSION
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There is disclosed an oral pharmaceutical formulation of bitter compounds that are agonists of TAS2R receptors for the treatment of pulmonary hypertension (PAH). More specifically, there is disclosed a PAH oral formulation comprising a bitter agent selected from the group consisting of 3-caffeoylquinic-1,5-lactone (3-CQL), chlorogenic acid (CGA), denatonium benzoate (DB), denatonium chloride (DC), denatonium saccharide (DS), denatonium acetate (DA), and combinations thereof and a PDE-5 inhibitor.
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Page/Page column 11-12
(2020/02/06)
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- 1 - O - dicafeoyl quininic acid, its derivatives, preparation method and use thereof (by machine translation)
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The invention of the formula (II) as shown by a 1 - O - caffenoylquinate acid derivatives, and 1 - O - dicafeoyl quininic acid, of formula (II) as shown by a 1 - O - caffenoylquinate acid derivatives and its application of salt. 1 - O - dicafeoyl quininic acid, of formula (II) as shown by a 1 - O - caffenoylquinate acid derivatives and the salts thereof inhibit interleukin 17, in particular interleukin 17 F of secretion, and capable of preventing and treating the tumor. Experimental results show that, 1 - O - dicafeoyl quininic acid concentration is 0.5 μm/L when the interleukin 17 F inhibition rate of close to 70%; 1 - O - dicafeoyl quininic acid in 20 mg/kg at a dose to the melanoma, pancreatic cancer, colorectal cancer, lung cancer tumor has good inhibition effect, are more than 50%, and its derivatives black pigment lump, pancreatic cancer, colorectal cancer, lung cancer tumor also has better inhibition effect. (by machine translation)
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Paragraph 0116; 0117; 0118; 0119
(2018/06/16)
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- Design, synthesis, and biological evaluation of novel tetramethylpyrazine derivatives as potential neuroprotective agents
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Oxidative stress plays a crucial role in neurological diseases, resulting in excessive production of reactive oxygen species, mitochondrial dysfunction and cell death. In this work, we designed and synthesized a series of tetramethylpyrazine (TMP) derivatives and investigated their abilities for scavenging free radicals and preventing against oxidative stress-induced neuronal damage in vitro. Among them, compound 22a, consisted of TMP, caffeic acid and a nitrone group, showed potent radical-scavenging activity. Compound 22a had broad neuroprotective effects, including rescuing iodoacetic acid-induced neuronal loss, preventing from tert-butylhydroperoxide (t-BHP)-induced neuronal injury. Compound 22a exerted its neuroprotective effect against t-BHP injury via activation of the phosphatidyl inositol 3-kinase (PI3K)/Akt signaling pathway. Furthermore, in a rat model of permanent middle cerebral artery occlusion, compound 22a significantly improved neurological deficits, and alleviated the infarct area and brain edema. In conclusion, our results suggest that compound 22a could be a potential neuroprotective agent for the treatment of neurological disease, particularly ischemic stroke.
- Chen, Haiyun,Tan, Guolian,Cao, Jie,Zhang, Gaoxiao,Yi, Peng,Yu, Pei,Sun, Yewei,Zhang, Zaijun,Wang, Yuqiang
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- Study on the anticoagulant or procoagulant activities of type II phenolic acid derivatives
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In this study, three type II phenolic acids (caffeic acid, p-hydroxycinnamic acid, and ferulic acid) were used to synthesize a total of 18 phenolic acid derivatives. With molecular docking for molecule design and target protein (factors) screening, in combination with the confirmation of target proteins (factors) by surface plasmon resonance, and the evaluation of haemostatic and anticoagulant activities with five blood assays (plasma recalcification time, prothrombin time, activated partial thromboplastin time, fibrinogen, and thrombin time), the data indicated that caffeic acid derivatives showed certain anticoagulant or procoagulant activities and that two other series contained compounds with the best anticoagulant activities. Using Materials Studio analysis, particular functional groups that affect anticoagulant or procoagulant activities were revealed, and these conclusions can guide the discovery of compounds with better activities.
- Luo, Xuan,Du, Chuanrong,Cheng, Hui,Chen, Jian-hua,Lin, Cuiwu
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- Phenethyl alcohol glucoside analogue and its synthetic method and application (by machine translation)
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The invention discloses phenethyl alcohol glucoside analogue and its synthetic method and application. The invention uses biological electronic isostere of such drugs design principle obtain a series of a kind of transformation with neuroprotective activity of the phenethyl alcohol glucoside derivative, sialic acid methyl ester derivatives and 9 the methcoside [...] decarboxylative rosmarinic acid compounds. The invention further provides a method for synthesizing analogs of phenethyl alcohol glucoside. Nerve pharmacological experimental study found, the breeding invention benzene through like apoptotic, to anti-oxidative damage, increasing the cell survival, reduce the apoptosis rate, inhibiting the production of reactive oxygen species in cells, significantly reducing the damage of the cells, play a neuroprotective role. Phenethyl alcohol glucoside provided by the invention includes analogs in the prevention or treatment of neurodegenerative disease, cerebral ischemia, in neurological disorders has important application potential. (by machine translation)
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Paragraph 0097; 0098
(2017/06/02)
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- METHOD FOR MANUFACTURING 3,4,5-TRICAFFEOYLQUINIC ACID
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Provided are a method for manufacturing 3,4,5-tricaffeoylquinic acid, which can produce 3,4,5-tricaffeoylquinic acid with high efficiency by a simple operation in a short process using inexpensive raw materials, and intermediate compounds. The method for manufacturing 3,4,5-tricaffeoylquinic acid of the invention includes at least Step (1) of allowing a compound represented by Formula (1) or a compound represented by Formula (2) to react with a compound represented by Formula (4); and Step (2) of deprotecting the product obtained in Step (1), and producing 3,4,5-tricaffeoylquinic acid:
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Paragraph 0383; 0384
(2016/02/19)
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- Discovery of oral-available resveratrol-caffeic acid based hybrids inhibiting acetylated and phosphorylated STAT3 protein
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Constitutive activation of STAT3 has been found in a wide variety of cancers and demonstrated as a very attractive therapeutic target. Disrupting both acetylation and phosphorylation of STAT3 protein was hypothesized to greatly deactivate STAT3, therefore, treating cancers. To demonstrate the hypothesis, two series of novel resveratrol-caffeic acid hybrids were designed aiming to regulate both acetylation and phosphorylation of STAT3 protein, which is also the first report of the synthetic inhibitors simultaneously regulating two biological reactions of STAT3 to our knowledge. Most of these compounds were demonstrated with preferential antitumor activity with low IC50values against two cancer cell lines. Particularly, compound 7d was found as an excellent STAT3 inhibitor with over 50-fold better potency than resveratrol and caffeic acid. Meanwhile, the novel derivatives significantly inhibited the proliferation and induced the apoptosis of tumor cells. Molecular docking further disclosed the binding modes of STAT3 with the inhibitors. In addition, compound 7d orally and significantly suppressed breast cancer 4T1 xenograft tumor growth in vivo, indicating its great potential as an efficacious drug candidate for human cancer therapy.
- Li, Shanshan,Zhang, Wenda,Yang, Yanwei,Ma, Ting,Guo, Jianpeng,Wang, Shanshan,Yu, Wenying,Kong, Lingyi
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p. 1006 - 1018
(2016/11/09)
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- Seven leaf lactone derivative and its preparation method and application
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The invention relates to an esculetin derivative, belonging to the field of specific curative activities of compounds or pharmaceutical preparation. The name of the derivative is 6,7-bi(5,6-diacetylcaffeoyl)-coumacetate, and the structural formula is as shown in the specification. The esculetin derivative disclosed by the invention is synthesized by taking natural medicinal monomers esculetin and caffeic acid as raw materials. The invention also provides a preparation method and application of the derivative. The derivative disclosed by the invention is a novel compound with good pharmaceutical activity, and the esculetin derivative prepared by the invention is subjected to raw material application in medicines for treating fever, inflammation and pain and has the effect of treating the fever, inflammation and pain.
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Paragraph 0035-0038
(2017/02/02)
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- Synthesis and biological evaluation of novel curcuminoid derivatives
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Curcuminoids have been reported to possess multiple bioactivities, such as antioxidant, anticancer and anti-inflammatory properties. Three novel series of curcuminoid derivatives (11a-h, 15a-h and 19a-d) with enhanced bioactivity have been synthesized. Among the synthesized compounds, 11b exhibited the most significant activity with an MIC of 0.5 μ M /mL against selected medically important Gram-positive cocci (S aureus and S viridans) and Gram-negative bacilli (E. coli and E. cloacae). The derivatives exhibited remarkable results in an antioxidant test with an IC50 2.4- to 9.3-folder smaller than curcuminoids. With respect to antiproliferative activity against Hep-G2, LX-2, SMMC7221 and MDA-MB-231, the derivatives exhibited an effect stronger than curcuminoids with an IC50 ranging from 0.18 to 4.25 μ M.
- Cao, Ya-Kun,Li, Hui-Jing,Song, Zhi-Fang,Li, Yang,Huai, Qi-Yong
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p. 16349 - 16372
(2015/01/08)
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- Synthesis and in vitro biological evaluation of nitric oxide-releasing derivatives of hydroxylcinnamic acids as anti-tumor agents
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Novel furoxan-based nitric oxide-releasing derivatives 6a-p of hydroxylcinnamic acids were synthesized by coupling the carboxyl group of hydroxylcinnamic acids with furoxan through various alkylol amines. Compounds 6a, e-i and m-p displayed more potent anti-tumor activities superior to control 5-fluorouracil (5-FU) in most cancer cells tested. Furthermore, 6f could selectively inhibit tumor cells, but not non-tumor cell proliferation. This inhibition was attributed to high levels of NO released in cancer cells and potentially synergistic effect of NO donor moieties and the bioactivity of hydroxylcinnamic acids.
- Lu, Ming-Dong,Zhou, Xiao,Yu, Yao-Jun,Li, Pi-Hong,Sun, Wei-Jian,Zhao, Cheng-Guang,Zheng, Zhi-Qiang,You, Tao,Wang, Fei-Hai
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p. 415 - 418
(2013/07/25)
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- Donor specificity and regioselectivity in Lipolase mediated acylations of methyl α-d-glucopyranoside by vinyl esters of phenolic acids and their analogues
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Methyl α-d-glucopyranoside as a model acceptor was acylated by several phenolic and non-phenolic vinyl esters using immobilised Lipolase. Donor specificity and regioselectivity of reaction were investigated. Conversion and rate of acylation by structurally varied donors indicates that the synthetic reactivity of Lipolase corresponds to the hydrolytic activity of feruloyl esterase type A. Lipolase exhibited remarkable regioselectivity for primary position of methyl α-d-glucopyranoside. The acylation occurred exclusively at 6-O primary position when vinyl esters of phenolic acids (hydroxybenzoates, hydroxyphenylalkanoates and hydroxycinnamates) served as acyl donors (5-77%). In addition to the major 6-O-acyl products (52-79%), 2,6-di-O-acylated derivatives were isolated from reaction mixtures (2-13%) when non-phenolic donors were used (vinyl esters of fully methoxylated derivatives of phenolic acids, along with vinyl benzoates, cinnamates or some heterocyclic analogues).
- Mastihubova, Maria,Mastihuba, Vladimir
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supporting information
p. 5389 - 5392
(2013/09/23)
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- Antiproliferative, antiandrogenic and cytotoxic effects of novel caffeic acid derivatives in LNCaP human androgen-dependent prostate cancer cells
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Caffeic acid and its naturally occurring derivative caffeic acid phenethyl ester (CAPE) have antiproliferative and cytotoxic properties in a variety of cancer cell lines without displaying significant toxicity toward healthy cells, and are considered to be potential anticancer agents. However, little is known about their effects on prostate cancer cells. We synthesized and evaluated the effects of caffeic acid, CAPE (2) and 18 synthetic derivatives on cell viability and androgen-dependent cell proliferation, subcellular localisation and expression of androgen receptor (AR) and secretion of prostate-specific antigen (PSA) in LNCaP human hormone-dependent prostate cancer cells. Several synthetic derivatives of CAPE were strong, concentration-dependent cytotoxic agents in LNCaP cells with IC50 values in the 6.8-26.6 μM range, potencies that were up to five-fold greater than that of CAPE (33.7 ± 4.0 μM). A number of caffeic acid derivatives were inhibitors of androgen-stimulated LNCaP cell proliferation with concomitant inhibition of DHT-stimulated PSA secretion. Compound 24 was the most cytotoxic and antiproliferative caffeic acid derivative (IC50 values of 6.8 ± 0.3 and 2.4 ± 0.8 μM, respectively) inhibiting DHT-stimulated cell proliferation and PSA secretion statistically significantly at concentrations as low as 0.3 μM. Exposure to DHT increased cytoplasmic and nuclear AR levels and co-treatment with increasing concentrations of compound 24 or CAPE (2), notably, further increased these levels. In conclusion, a number of synthetic derivatives of caffeic acid are potent inhibitors of androgen-dependent prostate cancer cell proliferation and viability, acting, at least in part, via an antiandrogenic mechanism that involves increased nuclear accumulation of (presumably inactive) AR.
- Sanderson, J. Thomas,Clabault, Hélène,Patton, Cody,Lassalle-Claux, Grégoire,Jean-Fran?ois, Jacques,Paré, Aurélie F.,Hébert, Martin J.G.,Surette, Marc E.,Touaibia, Mohamed
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p. 7182 - 7193
(2013/11/06)
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- Synthesis and antiradical/antioxidant activities of caffeic acid phenethyl ester and its related propionic, acetic, and benzoic acid analogues
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Caffeic acid phenethyl ester (CAPE) is a bioactive component isolated from propolis. A series of CAPE analogues was synthesized and their antiradical/antioxidant effects analyzed. The effect of the presence of the double bond and of the conjugated system on the antioxidant effect is evaluated with the analogues obtained from 3-(3,4-dihydroxyphenyl) propanoic acid. Those obtained from 2-(3,4-dihydroxyphenyl) acetic acid and 3,4-dihydroxybenzoic acid allow the evaluation of the effect of the presence of two carbons between the carbonyl and aromatic system.
- LeBlanc, Luc M.,Pare, Aurelie F.,Jean-Francois, Jacques,Hebert, Martin J.G.,Surette, Marc E.,Touaibia, Mohamed
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p. 14637 - 14650
(2013/03/13)
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- The design, synthesis and in vitro immunosuppressive evaluation of novel isobenzofuran derivatives
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The synthesis and biological evaluation of a series of novel isobenzofuran-based compounds are described. The compounds were evaluated for their immunosuppressive effects of T-cell proliferation and IMPDH type II inhibitor activity in vitro, as well as their structure-activity relationships were assessed. Several compounds demonstrated highly efficacious immunosuppressive properties, especially compounds 2d, 2e, 2h and 2j, which were superior to MPA, while compounds 2k, 2m, 2n, 4c and 5d exhibited an equipotent inhibitory activity compared to MPA. Generally, it was obviously demonstrated that α,β-unsaturated amides proved more potent than the diamide and urea series. The present study provides a guide for further research on development of safe and effective immunosuppressive agents.
- Yang, Na,Wang, Qing-He,Wang, Wen-Qian,Wang, Jian,Li, Feng,Tan, Shen-Peng,Cheng, Mao-Sheng
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body text
p. 53 - 56
(2012/02/16)
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- Syntheses of antioxidant flavonoid derivatives
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Quercetin-caffeic acid and quercetin-curcumin conjugates have been synthesized as potent antioxidants to prevent age-related macular degeneration. Thus, the widely disributed plant antioxidant quercetin was linked to other plant antioxidants, caffeic acid and curucumin, to enhance its antioxidative properties. The Japan Institute of Heterocyclic Chemistry.
- Yanase, Emiko,Jang, Young P.,Nakanishi, Koji
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scheme or table
p. 1151 - 1155
(2011/05/05)
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- Structure-activity relationship of caffeoylquinic acids on the accelerating activity on ATP production
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Caffeoylquinic acid (CQA) is one of the phenylpropanoids which have various bioactivities such as antioxidant, antibacterial, anticancer, antihistamic, and other biological effects. We previously reported that 3,5-di-O-caffeoylquinic acid inhibited amyloid β1-42-induced cellular toxicity on human neuroblastoma SH-SY5Y cells and increased the mRNA expression level of glycolytic enzymes and the intracellular ATP level. To investigate structure-activity relationship on the accelerating activity on ATP production, we synthesized 1,4,5-tri-O-caffeoylquinic acid, 4,5-di-O-caffeoylquinic acid, 3,4,5-tri-O-caffeoylquinic acid, and other derivatives. Additionally, we evaluated intracellular ATP level in SH-SY5Y treated with each CQA derivative. As a result, 3,4,5-tri-O-caffeoylquinic acid showed the highest accelerating activity on ATP production among tested compounds. It was suggested that caffeoyl groups bound to quinic acid are important for activity and the more caffeoyl groups are bound to quinic acid, the higher accelerating activity on ATP production exhibits.
- Miyamae, Yusaku,Kurisu, Manami,Han, Junkyu,Isoda, Hiroko,Shigemori, Hideyuki
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body text
p. 502 - 507
(2011/06/10)
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- TOLL LIKE RECEPTOR (TLR) SIGNALING ANTAGONIST
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The present invention relates to novel synthetic toll like receptor antagonist. The present invention in particular provides compounds, methods and compositions for specifically inhibiting immune stimulation involving TLR ligands, especially TLR-4. The compounds are potentially useful in treatment of inflammation, autoimmunity, allergy, asthma, graft rejection, graft versus host disease, infection, sepsis, cancer and immunodeficiency.
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Page/Page column 12
(2009/09/07)
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- ANTIOXIDANT FLAVONOID DERIVATIVES
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The present invention relates to antioxidant flavonoids, compositions containing such antioxidant flavonoids, methods for using such antioxidant flavonoids to treat, e.g., AMD, and methods for making such antioxidant flavonoids. Also provided are methods for ameliorating A2E photooxidation, especially in cells and mammals, particularly, humans.
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Page/Page column 41-42; 43
(2009/06/27)
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- Design and synthesis of novel nitrogen-containing polyhydroxylated aromatics as HIV-1 integrase inhibitors from caffeic acid phenethyl ester
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A series of nitrogen-containing polyhydroxylated aromatics from caffeic acid phenethyl ester were designed and synthesized as HIV-1 integrase inhibitors. Most of these compounds exhibited potent inhibitory activities at micromolar concentrations against HIV-1 integrase in the 3′-end processing and the strand transfer. Their key structure-activity relationship was also discussed.
- Wang, Peng,Liu, Chuan,Sanches, Tino,Zhong, Yuan,Liu, Bo,Xiong, Junlong,Neamati, Nouri,Zhao, Guisen
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supporting information; experimental part
p. 4574 - 4578
(2010/04/24)
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- COMPOSITION COMPRISING DECURSIN DERIVATIVE FOR TREATING AND PREVENTING ATOPIC DERMATITIS
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The present invention relates to the novel decursin derivatives, the preparation thereof and the composition comprising the same. The novel decursin derivatives of the present invention showedpotent inhibiting activity of the release of MCP-1, IL-6 and IL-8 induced by dermite in THP-1 or EoL-1 cell, therefore the compounds can be useful in treating or preventing atopic dermatitis.
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Page/Page column 47-48
(2008/12/08)
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