- POLYPHENOL-PEPTIDE CONJUGATES FOR NUCLEAR-TARGETED DELIVERY
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The present invention relates to a polyphenol-peptide conjugate composed of: (i) a peptide comprising the amino acid sequence Arg-Arg-X1-Leu, wherein X1 refers to one or two hydrophobic amino acids selected independently from lie, Leu, Val, Phe, Trp, and
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- Design, synthesis and pharmacological evaluation of ester-based quercetin derivatives as selective vascular KCa1.1 channel stimulators
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Quercetin represents one of the most studied dietary flavonoids; it exerts a panel of pharmacological activities particularly on the cardiovascular system. Stimulation of vascular KCa1.1 channels contributes to its vasorelaxant activity, which
- Carullo, Gabriele,Ahmed, Amer,Trezza, Alfonso,Spiga, Ottavia,Brizzi, Antonella,Saponara, Simona,Fusi, Fabio,Aiello, Francesca
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- Preparation method of 3,5,3',4'-tetraacetoxy-7-hydroxyflavone
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The invention provides a preparation method of 3,5,3',4'-tetraacetoxy-7-hydroxyflavone. The method comprises the following steps: in the presence of a solvent, mixing 3,5,7,3',4'-pentaacetoxyflavone,pyridine hydrochloride and silica gel; and then, after the solvent is removed, carrying out a reaction at a first temperature to obtain the 3,5,3',4'-tetraacetoxy-7-hydroxyflavone. According to the preparation method disclosed by the invention, the position 7 of 3,5,7,3',4'-pentaacetoxyflavone is subjected to a deacetylation reaction in a high-selectivity manner by virtue of the synergistic effectof the silica gel and pyridine hydrochloride, and reagents with relatively high toxicity are not used, so the preparation method is high in safety and simple to operate.
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Paragraph 0026-0039
(2020/07/02)
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- Silica particles with a quercetin-R5 peptide conjugate are taken up into HT-29 cells and translocate into the nucleus
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Intracellular delivery of bioactive polyphenols is currently evaluated as a protective strategy for cells under pharmaceutical stress. To this end, the 20mer R5 peptide from the marine diatom C. fusiformis was N-terminally modified with a quercetin deriva
- Del Favero, Giorgia,Bialas, Friedrich,Grabher, Stephanie,Wittig, Anja,Br?uer, Birgit,Gerthsen, Dagmar,Echalier, Cécile,Kamalov, Meder,Marko, Doris,Becker, Christian F. W.
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p. 9649 - 9652
(2019/08/15)
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- Quercetin derivative and its preparation method and application
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The invention discloses a quercetin derivative and a preparation method and application thereof. The preparation method comprises the following steps: firstly using dichlorodiphenylmethane to protect quercetin o-diphenol hydroxyl, combining a benzyl protection group to obtain the selectively protected quercetin derivative, and then independently reacting with dimethyl sulfate, diethyl sulfate, allyl bromide, paratoluensulfonyl chloride and acetic anhydride respectively to generate corresponding quercetin derivatives. All of the prepared derivative compounds have NRK-49F proliferation activity inhibition superior to that of quercetin. The quercetin derivatives 20a-1, 14a-1 and 23d-1 compositely replaced by methyl and p-tosyl have higher inhibition NRK-49F proliferation activity, and the inhibition ratio respectively reaches 86.33%, 78.04% and 75.91%. Thus, the currently obtained quercetin derivative compounds have obvious inhibition effect on kidney fibroblast NRK-49F proliferation.
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- Method for preparing 3,3',4',5-tetra-O-acylated quercetin
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The invention relates to the field of organic small molecule synthesis, in particular to a technology for synthesizing 3,3',4',5-tetra-O-acylated quercetin. The technology comprises the synthesizing steps that 1, quercetin serves as a substrate, acyl chlo
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Paragraph 0018; 0019
(2016/11/24)
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- Utilization of the inherent nucleophile for regioselective O-acylation of polyphenols via an intermolecular cooperative transesterification
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A green and efficient method for regioselective O-acylation of polyphenols has been developed. The acylation can be carried out in potassium carbonate/dimethyl sulphoxide system by utilizing the ‘inherent nucleophile’ via an intermolecular cooperative transesterification under mild condition. This method shows particular advantage in regioselective acylation of polyphenols bearing 2′,4′-dihydroxyacetophenone moiety and can be extended to the synthesis of mono or multiple acetates of polyphenols without this moiety in good yields. Compared with other reported approaches, this method is endowed with atom economy and is more environment-friendly for avoiding the use of any metal-based catalysts.
- Liu, Jingchao,Fu, Junjie,Li, Wenlong,Zou, Yu,Huang, Zhangjian,Xu, Jinyi,Peng, Sixun,Zhang, Yihua
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supporting information
p. 4103 - 4110
(2016/07/06)
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- Discovery of metal ions chelator quercetin derivatives with potent anti-HCV activities
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Analogues or isosteres of α,γ-diketoacid (DKA) 1a show potent inhibition of hepatitis C virus (HCV) NS5B polymerase through chelation of the two magnesium ions at the active site. The anti-HCV activity of the flavonoid quercetin ( 2) could partly be attri
- Zhong, Dongwei,Liu, Mingming,Cao, Yang,Zhu, Yelin,Bian, Shihui,Zhou, Jiayi,Wu, Fengjie,Ryu, Kum-Chol,Zhou, Lu,Ye, Deyong
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p. 6978 - 6999
(2015/05/13)
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- Design and discovery of flavonoid-based HIV-1 integrase inhibitors targeting both the active site and the interaction with LEDGF/p75
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HIV integrase (IN) is an essential enzyme for the viral replication. Currently, three IN inhibitors have been approved for treating HIV-1 infection. All three drugs selectively inhibit the strand transfer reaction by chelating a divalent metal ion in the
- Li, Bo-Wen,Zhang, Feng-Hua,Serrao, Erik,Chen, Huan,Sanchez, Tino W.,Yang, Liu-Meng,Neamati, Nouri,Zheng, Yong-Tang,Wang, Hui,Long, Ya-Qiu
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p. 3146 - 3158
(2014/06/09)
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- Quercetin-POC conjugates: Differential stability and bioactivity profiles between breast cancer (MCF-7) and colorectal carcinoma (HCT116) cell lines
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In the course of our ongoing efforts to develop novel quercetin conjugates with enhanced stability profiles, we introduced an isopropyloxycarbonylmethoxy (POC) group to 7-OH and/or 3-OH of quercetin and prepared three novel quercetin conjugates. The querc
- Cho, Suh Young,Kim, Mi Kyoung,Park, Kwang-Su,Choo, Hyunah,Chong, Youhoon
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p. 1671 - 1679
(2013/05/08)
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- An efficient method for C8-prenylation of flavonols and flavanones
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Synthesis of C8-prenylated flavonols and flavanones via the palladium-catalyzed 7-O-1,1-dimethylprop-2-enylation, followed by Claisen rearrangement is described. Two regioselectivities (carbon-carbon bond formation at either the tail or head of the prenyl
- Kawamura, Tomoyuki,Hayashi, Moemi,Mukai, Rie,Terao, Junji,Nemoto, Hisao
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p. 1308 - 1314
(2012/06/30)
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- Synthesis and antiviral evaluation of 7-O-arylmethylquercetin derivatives against SARS-associated coronavirus (SCV) and hepatitis C virus (HCV)
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Aryl diketoacid (ADK) is well known for antiviral activity which can be enhanced by introduction of an aromatic arylmethyl substituent. A natural flavonoid quercetin has a 3,5-dihydroxychromone pharmacophore which is in bioisosteric relationship with the
- Park, Hye Ri,Yoon, Hyunjun,Kim, Mi Kyoung,Lee, Sung Dae,Chong, Youhoon
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- Biotinylated quercetin as an intrinsic photoaffinity proteomics probe for the identification of quercetin target proteins
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Quercetin is a flavonoid natural product, that is, found in many foods and has been found to have a wide range of medicinal effects. Though a number of quercetin binding proteins have been identified, there has been no systematic approach to identifying a
- Wang, Rongsheng E.,Hunt, Clayton R.,Chen, Jiawei,Taylor, John-Stephen
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experimental part
p. 4710 - 4720
(2011/09/20)
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- Regioselective O-derivatization of quercetin via ester intermediates. An improved synthesis of rhamnetin and development of a new mitochondriotropic derivative
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The regioselective synthesis of several quercetin (3,3',4',5,7-pentahydroxy flavone) tetraesters bearing a single free OH on 5-C was achieved in good yield by proper choice of reaction conditions using common esterification procedures. Tetracetylated quercetin with the free OH on 7-C was selectively obtained instead via imidazole-promoted deacylation of the corresponding pentaester. Unambiguous structural characterization of the two isomeric tetraacetyl quercetin derivatives was obtained by combined HSQC and HMBC 2D-NMR analysis. These molecules can be used as starting materials for the regioselective synthesis of other derivatives. High yield syntheses of the natural polyphenol rhamnetin (7-O-methylquercetin) and of the new mitochondriotropic compound 7-(4-triphenylphosphoniumbutyl) quercetin iodide are reported as examples.
- Mattarei, Andrea,Biasutto, Lucia,Rastrelli, Federico,Garbisa, Spiridione,Marotta, Ester,Zoratti, Mario,Paradisi, Cristina
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experimental part
p. 4722 - 4736
(2010/10/20)
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- Enhanced stability and intracellular accumulation of quercetin by protection of the chemically or metabolically susceptible hydroxyl groups with a pivaloxymethyl (POM) promoiety
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In order to increase stability of quercetin, its metabolically and chemically susceptible hydroxyl groups 7-OH and 3-OH respectively were transiently blocked with a pivaloxymethyl (POM) promoiety to provide two novel quercetin conjugates [7-O-POM-Q (2), 3
- Kim, Mi Kyoung,Park, Kwang-Su,Lee, Chaewoon,Park, Hye Ri,Choo, Hyunah,Chong, Youhoon
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experimental part
p. 8597 - 8607
(2011/02/25)
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- Investigation of the pharmacophore space of Severe Acute Respiratory Syndrome coronavirus (SARS-CoV) NTPase/helicase by dihydroxychromone derivatives
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Aryl diketoacids have been identified as the first SARS-CoV NTPase/helicase inhibitors with a distinct pharmacophore featuring an arylmethyl group attached to a diketoacid. In order to search for the pharmacophore space around the diketoacid core, three c
- Lee, Chaewoon,Lee, Jin Moo,Lee, Na-Ra,Kim, Dong-Eun,Jeong, Yong-Joo,Chong, Youhoon
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experimental part
p. 4538 - 4541
(2010/04/03)
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- Facile synthesis of flavonoid 7-O-glycosides
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Highly regioselective removal of the 7-O-acyl groups of the peracylated flavones, isoflavones, and flavonols (PhSH, imidazole, NMP) followed by effective glycosylation with glycosyl trifluoroacetimidates (BF 3·Et2O) and cautious deprotection of the acyl groups under basic conditions afforded the desired 7-O-flavonoid glycosides in satisfactory yields.
- Li, Ming,Han, Xiuwen,Yu, Biao
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p. 6842 - 6845
(2007/10/03)
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