4'-O-carboxymethyl-genistein

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 4'-O-carboxymethyl-genistein
• 英文别名: 2-[4-(5,7-Dihydroxy-4-oxochromen-3-yl)phenoxy]acetic acid
• 化学式: C₁₇H₁₂O₇
• 分子量: 328.278
• InChiKey: BQHSNLYCWMQWAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  染料木素 在 potassium tert-butylate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 4'-O-carboxymethyl-genistein
  参考文献：
  名称：

  Time-resolved fluoroimmunoassay of plasma daidzein and genistein11Abbreviations: Daidzein (Da), genistein (Gen), gas-liquid chromatography (GC), high performance liquid chromatography (HPLC), mass spectrometry (MS), radioimmunoassay (RIA), time-resolved fluoroimmunoassay (TR-FIA), enzymeimmunoassay (EIA), fluoroimmunoassay (FIA), bovine serum albumin (BSA), N,N′-dicyclohexylcarbodiimide (DCC), N-hydroxysuccinimide (NHS), isotope dilution gas chromatography-mass spectrometry in the selected ion monitoring mode (ID-GC-MS-SIM), coefficients of variation (CVs). B = Binding of tracer to antibody in the presence of unlabeled analyte. B0 = Binding of tracer to antibody in the absence of unlabeled analyte. T = Total amount of tracer added. Estradiol = estradiol-17β.

  摘要：

  We present a method for the determination of the phytoestrogens daidzein and genistein in plasma (serum). These weakly estrogenic isoflavones occur in soybeans and in smaller amounts in some other beans and plants. It has been suggested that they may afford protection against prostate and breast cancer. The method is based on time-resolved fluoroimmunoassay (TR-FIA) using a europium chelate as a label. After synthesis of 4'-O-carboxymethyl-daidzein and 4'-O-carboxymethyl-genistein the compounds are coupled to bovine serum albumin (BSA), then used as antigens to immunize rabbits. The tracers with the europium chelate are synthesized using the same 4'-O-derivative of the isoflavones. After enzymatic hydrolysis and ether extraction the immunoassay is carried out using the VICTOR 1420 multilabel counter (Wallac Oy, Turku, Finland). The antisera cross-reacted to some extent with some isoflavonoids but not with flavonoids. The cross-reactivity seems not to influence the results, which were highly specific for both compounds. The correlation coefficients between the TR-FIA methods and the reference method based on isotope dilution gas chromatography-mass spectrometry were high; r-values were about 0.95-0.99 depending on concentration. The intra-assay coefficients of variation (CV%) for daidzein and genistein at three different concentrations vary 3.2-4.5 and 3.2-4.1, respectively. The inter-assay CVs vary 5.0-6.3 and 4.5-5.3, respectively. The working ranges of the daidzein and genistein assays are 1.0-216 and 1.7-370 nmol/l, respectively. The plasma values (n = 80) of daidzein and genistein are very low in Finnish subjects (mean for daidzein, 3.8 +/- 6.8 and for genistein, 3.2 +/- 7.6 nmol/l; median value for daidzein 1.5 and for genistein 1.4 nmol/l). (C) 2000 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(00)00089-1

文献信息

• METHODS AND COMPOUNDS FOR THE TARGETED DELIVERY OF AGENTS TO BONE FOR INTERACTION THEREWITH
  申请人：Pierce, JR. William M.

  公开号：US20090118164A1

  公开（公告）日：2009-05-07

  Bone targeted compounds and methods are provided. Compounds can include a Bone Targeting Portion (R T ), having an affinity for bone; a Bone Active Portion (R A ) for interacting with and affecting bone; and a Linking Portion (R L ) connecting the Bone Targeting Portion and the Bone Active Portion.

  提供了针对骨骼的化合物和方法。化合物可以包括具有对骨骼亲和力的骨靶向部分（RT）；用于与骨骼相互作用和影响骨骼的骨活性部分（RA）；以及连接骨靶向部分和骨活性部分的连接部分（RL）。
• US8071575B2
  申请人：——

  公开号：US8071575B2

  公开（公告）日：2011-12-06
• [EN] METHODS AND COMPOUNDS FOR THE TARGETED DELIVERY OF AGENTS TO BONE FOR INTERACTION THEREWITH<br/>[FR] PROCÉDÉS ET COMPOSÉS POUR LA DÉLIVRANCE CIBLÉE D'AGENTS À UN OS POUR UNE INTERACTION AVEC CET OS
  申请人：UNIV LOUISVILLE RES FOUND

  公开号：WO2008103951A1

  公开（公告）日：2008-08-28

  [EN] Bone targeted compounds and methods are provided. Compounds can include a Bone Targeting Portion (RT), having an affinity for bone; a Bone Active Portion (RA) for interacting with and affecting bone; and a Linking Portion (RL) connecting the Bone Targeting Portion and the Bone Active Portion.
  [FR] L'invention concerne des composés et des procédés ciblant les os. Les composés peuvent comprendre une partie ciblant l'os (RT), qui présente une affinité pour les os ; une partie active envers l'os (RA), qui est destinée à interagir avec l'os et à affecter l'os ; et une partie de liaison (RL), qui est destinée à connecter la partie ciblant l'os et la partie active envers l'os.
• Time-resolved fluoroimmunoassay of plasma daidzein and genistein11Abbreviations: Daidzein (Da), genistein (Gen), gas-liquid chromatography (GC), high performance liquid chromatography (HPLC), mass spectrometry (MS), radioimmunoassay (RIA), time-resolved fluoroimmunoassay (TR-FIA), enzymeimmunoassay (EIA), fluoroimmunoassay (FIA), bovine serum albumin (BSA), N,N′-dicyclohexylcarbodiimide (DCC), N-hydroxysuccinimide (NHS), isotope dilution gas chromatography-mass spectrometry in the selected ion monitoring mode (ID-GC-MS-SIM), coefficients of variation (CVs). B = Binding of tracer to antibody in the presence of unlabeled analyte. B0 = Binding of tracer to antibody in the absence of unlabeled analyte. T = Total amount of tracer added. Estradiol = estradiol-17β.
  作者：Guojie J Wang、Oldrich Lapcı́k、Richard Hampl、Mariko Uehara、Nawaf Al–Maharik、Katariina Stumpf、Heikki Mikola、Kristiina Wähälä、Herman Adlercreutz

  DOI：10.1016/s0039-128x(00)00089-1

  日期：2000.6

  We present a method for the determination of the phytoestrogens daidzein and genistein in plasma (serum). These weakly estrogenic isoflavones occur in soybeans and in smaller amounts in some other beans and plants. It has been suggested that they may afford protection against prostate and breast cancer. The method is based on time-resolved fluoroimmunoassay (TR-FIA) using a europium chelate as a label. After synthesis of 4'-O-carboxymethyl-daidzein and 4'-O-carboxymethyl-genistein the compounds are coupled to bovine serum albumin (BSA), then used as antigens to immunize rabbits. The tracers with the europium chelate are synthesized using the same 4'-O-derivative of the isoflavones. After enzymatic hydrolysis and ether extraction the immunoassay is carried out using the VICTOR 1420 multilabel counter (Wallac Oy, Turku, Finland). The antisera cross-reacted to some extent with some isoflavonoids but not with flavonoids. The cross-reactivity seems not to influence the results, which were highly specific for both compounds. The correlation coefficients between the TR-FIA methods and the reference method based on isotope dilution gas chromatography-mass spectrometry were high; r-values were about 0.95-0.99 depending on concentration. The intra-assay coefficients of variation (CV%) for daidzein and genistein at three different concentrations vary 3.2-4.5 and 3.2-4.1, respectively. The inter-assay CVs vary 5.0-6.3 and 4.5-5.3, respectively. The working ranges of the daidzein and genistein assays are 1.0-216 and 1.7-370 nmol/l, respectively. The plasma values (n = 80) of daidzein and genistein are very low in Finnish subjects (mean for daidzein, 3.8 +/- 6.8 and for genistein, 3.2 +/- 7.6 nmol/l; median value for daidzein 1.5 and for genistein 1.4 nmol/l). (C) 2000 Elsevier Science Inc. All rights reserved.