[11C]methanol | 13036-26-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [11C]methanol
• 英文别名: <11C>methanol；[¹¹C]-methanol；[(11)C]methanol；[¹¹C]CH₃OH；[¹¹C]Methanol；(11)C-methanol；(111C)methanol
• CAS: 13036-26-5
• 化学式: CH₄O
• 分子量: 31.0312
• InChiKey: OKKJLVBELUTLKV-BJUDXGSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  2
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [11C]methanol 在 氢碘酸 作用下， 反应 0.08h， 生成 [11C]methyl iodide
  参考文献：
  名称：

  Synthesis and biodistribution of [¹¹C]SN-38

  摘要：

  SN-38（7-乙基-10-羟基喜树碱）是一种拓扑异构酶I抑制剂，是伊立替康的活性化疗药物，适用于结肠癌。由于对伊立替康治疗的反应率较低，因此寻找一个预后指标，以便识别和更有选择性地治疗可能对治疗有反应的患者，具有重要意义。因此，我们制备了标记了碳-11的SN-38。SN-38通过对3-[11C]丙醛的自由基氧化反应及随后将乙基片段自由基加到10-羟基喜树碱上制备而成。标记的丙醛是通过甲基碘与2-锂甲基-1,3-二恶烷反应制备的。总体化学收率为34%，来源于二氧化碳。通过正电子发射断层扫描（PET）测量了[11C]SN-38的小鼠生物分布和辐射剂量，以为首次人类研究做准备。生物分布相对均匀，除了肝胆和尿液排泄。版权所有 © 2010 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1746
• 作为产物：
  描述：

  [11C]methane 在 铁粉 、 一氧化二氮 作用下， 生成 [11C]methanol
  参考文献：
  名称：

  Sarkadi-Priboczki, E.; Elsinga, P. H.; Medema, J., Journal of labelled compounds and radiopharmaceuticals, 2001, vol. 44, p. S1026 - S1028

  摘要：

  DOI：

文献信息

• 亚氨基酸类PET显像剂及其制备方法与应用
  申请人：广东回旋医药科技股份有限公司

  公开号：CN103333079B

  公开（公告）日：2016-08-17

  本发明公开了一种亚氨基酸类正电子发射断层(PET)显像剂及其制备方法和应用，其属于N‑取代正电子核素标记谷氨基酸类化合物，其结构为：其中，L*＝‑11 ，‑CH2CH218F，‑COCH(18F)CH3；新型显像剂N‑(2‑18F‑氟丙酰基)‑谷氨酸显示很好的肿瘤PET显像灵敏性和特异性，对肿瘤(如S180纤维肉瘤)有很高的摄取，并且体内其他组织器官(除膀胱外)摄取不明显，显示了高的肿瘤与本底比值。体内外实验表明N‑(2‑18F‑氟丙酰基)‑谷氨酸在体内外较稳定，显示了很好的药代动力学特性。
• Highly efficient synthesis of [11C]Me-QNB, a selective radioligand for the quantification of the cardiac muscarinic receptors using PET
  作者：Fr�d�ric Dolle、Fran�oise Hinnen、Fran�oise Vaufrey、St�phane Demphel、Yann Bramoulle、Denis Fournier、Michel Ponchant、H�ric Valette、Christian Crouzel

  DOI：10.1002/jlcr.460

  日期：2001.4

  Me-QNB (N-methyl-quinuclidin-3-yl benzilate or N-methyl-quinuclidin-3-yl diphenylhydroxy acetate) is a hydrophilic, non-metabolized and highly specific muscarinic acetylcholinergic antagonist. Using this quaternary ammonium derivative of QNB, labelled with carbon-11, a positron-emitting isotope (half-life : 20.4 minutes), the potential for quantification of myocardial muscarinic receptors in vivo using the high-resolution, sensitive and quantitative imaging technique PET (positron emission tomography) was previously demonstrated in dogs and validated in humans. In this paper, the radiosynthesis of carbon-11-labelled Me-QNB is investigated and oriented towards the preparation of multi milliCuries of radiotracer. Typically, using no-carrier-added [11C]methyl triflate as the alkylating agent and 0.64 mg (1.89 µmol) of QNB as precursor for labelling at 100°C for 1 minute lead to a 48.5% +/−10% (15 runs) decay-corrected radiochemical yield (based on [11C]methyl triflate). 183 mCi (+/−39) of [11C]Me-QNB ([11C]-1) could be synthesized in only 27 to 28 minutes after EOB and occasionally, up to 340 mCi of [11C]Me-QNB ([11C]-1) were obtained, corresponding to a 85% decay-corrected yield. The associated decay-corrected specific radioactivities obtained were 2658 mCi/µmol (+/−971) at EOB. Copyright © 2001 John Wiley & Sons, Ltd.

  Me-QNB (N-甲基-喹宁环-3-基苄酯或N-甲基-喹宁环-3-基二苯羟乙酸酯)是一种亲水性、非代谢性和高度特异性的毒蕈碱型乙酰胆碱拮抗剂。使用这种标记有碳-11(一种正电子发射同位素，半衰期为20.4分钟)的QNB四级铵衍生物，先前已在狗中证明了利用高分辨率、灵敏和定量的成像技术(正电子发射断层扫描，PET)对心肌毒蕈碱受体进行定量测量的潜力，并在人类中得到了验证。本文研究了碳-11标记的Me-QNB的放射合成，旨在制备多毫居里的放射性示踪剂。通常，使用无载体添加的[11C]甲基三氟甲磺酸酯作为烷基化剂，并以0.64 mg (1.89 µmol)的QNB作为标记前体，在100°C下标记1分钟，得到48.5% ±10%(15次运行)的衰变校正放射化学产率(基于[11C]甲基三氟甲磺酸酯)。在EOB后仅27到28分钟内可以合成183 mCi (±39)的[11C]Me-QNB ([11C]-1)，偶尔可获得高达340 mCi的[11C]Me-QNB ([11C]-1)，对应于85%的衰变校正产率。在EOB时获得的关联衰变校正比活度为2658 mCi/µmol (±971)。版权所有 © 2001 John Wiley & Sons, Ltd.
• The synthesis of 4-(4-([11C]methoxyphenyl) -(5-fluoro-2-hydro-xyphenyl)-methylene-aminobutyric acid, as a potential radioli-gand for the gaba receptor in the brain
  作者：Filip De Vos、Guido Slegers

  DOI：10.1002/jlcr.2580340708

  日期：1994.7

  A procedure for the synthesis of 4-(4-[11C]methoxyphenyl) -(5-fluoro-2-hydroxyphenyl)-methylene-aminobutyric acid has been developed. The production entailed a O-methylation of 5-fluoro-2-hydroxy-4′-hydroxybenzophenone with cyclotron produced [11C]iodomethane in the presence of alkali and a subsequent Schiff reaction of 5-fluoro-2-hydroxy-4′-(11C]methoxybenzophenone with γ-aminobutyric acid. 5-Fluoro-2-hydroxy-4′-hydroxybenzophenone was obtained by a demethylation of the 4′-methoxyderivative with boron tribromide. Subsequent purification by HPLC and sterilisation by filtration gave 740 MBq (20 mCi) of an injectable solution. The radiochemical yield (decaycorrected) from [11C]iodomethane achieved 27%. The specific activity was 3.7 GBq/μmol (100 mCi/μmol) at the end of the radiosynthesis (45 min from EOB). The preparations have been demonstrated to be chemically and radiochemically pure by HPLC and TLC.

  已开发出一种合成4-(4-[11C]甲氧基苯基)-(5-氟-2-羟苯基)-甲亚胺基丁酸的方法。该生产过程包括在碱性条件下，用回旋加速器生产的[11C]碘甲烷对5-氟-2-羟基-4′-羟基二苯酮进行O-甲基化，随后与γ-氨基丁酸进行希夫反应。5-氟-2-羟基-4′-羟基二苯酮是通过用三溴化硼对4′-甲氧基衍生物进行脱甲基化得到的。随后通过HPLC纯化和过滤灭菌得到740 MBq（20 mCi）的可注射溶液。从[11C]碘甲烷获得的放射化学产率（衰变校正）为27%。在放射合成结束时（自EOB起45分钟），比活性为3.7 GBq/μmol（100 mCi/μmol）。通过HPLC和TLC证实制备物在化学和放射化学上是纯的。
• Fully automated high yield synthesis of (R)- and (S)-[11C]verapamil for measuring P-glycoprotein function with positron emission tomography
  作者：Gert Luurtsema、Albert D. Windhorst、Martien P.J. Mooijer、Jacobus D.M. Herscheid、Adriaan A. Lammertsma、Eric J.F. Franssen

  DOI：10.1002/jlcr.632

  日期：2002.12

  Racemic (±) verapamil is a well characterized substrate for P-glycoprotein (P-gp). However, the in vivo pharmacokinetics and pharmacodynamics of both enantiomers are reported to be different. In the preparation of evaluation studies of both enantiomers in animals and humans, the purpose of the present study was to optimize and automate the synthesis of (R)- and (S)-[11C]verapamil. (R)- and (S)-[11C]verapamil were prepared from (R)- and (S)-desmethyl-verapamil, respectively, by methylation with no-carrier added [11C]methyliodide or [11C]methyltriflate. Different conditions of the methylation reaction were studied: reaction time, temperature, base and solvent, and chemical form of the precursor using either the hydrochloric acid salt or the free base of the starting material. After optimization, the synthesis was fully automated using home-made modules and performed according to GMP guidelines. Optimal yields of 60–70% for the methylation reaction were obtained using 1.5 mg of the free base of (R)- or (S)-desmethyl-verapamil in 0.5 ml of acetonitrile at 50°C for 5 min with [11C]methyltriflate as methylating agent. Under the same reaction conditions, but with a reaction temperature of 100°C, the radiochemical yield starting with [11C]methyliodide as methylation reagent was 40%. The specific activity of (R)- and (S)-[11C]verapamil was >20 GBq/μmol and the radiochemical purity was >99% for both methods. The total synthesis time was 45 min. The automated high yield synthesis of (R)- and (S)-[11C]verapamil provides the means for evaluating both enantiomers as in vivo tracers of P-gp function. Copyright © 2002 John Wiley & Sons, Ltd.

  消旋(±)维拉帕米是一种已被充分表征的P-糖蛋白(P-gp)底物。然而,两种对映体的体内药代动力学和药效学报道存在差异。在动物和人类中对两种对映体进行评价研究的准备过程中,本研究旨在优化和自动化合成(R)-和(S)-[11C]维拉帕米。(R)-和(S)-[11C]维拉帕米分别由(R)-和(S)-去甲维拉帕米通过无载体添加的[11C]甲基碘或[11C]甲基三氟化硫进行甲基化制备。研究了甲基化反应的不同条件:反应时间、温度、碱和溶剂,以及使用起始物质的盐酸盐或游离碱作为前体的化学形式。经过优化后,根据GMP指南,使用自制模块实现了合成的完全自动化。使用1.5 mg的(R)-或(S)-去甲维拉帕米的游离碱在0.5 ml的乙腈中于50°C下反应5分钟,并以[11C]甲基三氟化硫作为甲基化剂,获得了60-70%的最佳甲基化反应产率。在相同的反应条件下,但反应温度为100°C时,以[11C]甲基碘作为甲基化试剂的放射化学产率为40%。(R)-和(S)-[11C]维拉帕米的比活度均>20 GBq/μmol,且两种方法的放射化学纯度均>99%。总合成时间为45分钟。(R)-和(S)-[11C]维拉帕米的自动高产率合成为评估两种对映体作为P-gp功能的体内示踪剂提供了手段。版权所有 © 2002 John Wiley & Sons, Ltd.
• Benzyl [¹¹C]Hippurate as an Agent for Measuring the Activities of Organic Anion Transporter 3 in the Brain and Multidrug Resistance-Associated Protein 4 in the Heart of Mice
  作者：Tatsuya Kikuchi、Toshimitsu Okamura、Maki Okada、Masanao Ogawa、Chie Suzuki、Hidekatsu Wakizaka、Joji Yui、Toshimitsu Fukumura、Antony D. Gee、Ming-Rong Zhang

  DOI：10.1021/acs.jmedchem.6b00454

  日期：2016.6.23

  Multidrug resistance-associated protein 4 (MRP4) and organic anion transporter 3 (OAT3) mediate the efflux of organic anions from the brain and heart. In this study, we have developed a probe for estimating the activity of these transporters in these tissues using positron emission tomography. Several 11C-labeled hippuric acid ester derivatives were screened with the expectation that they would be

  多药耐药相关蛋白4（MRP4）和有机阴离子转运蛋白3（OAT3）介导有机阴离子从大脑和心脏流出。在这项研究中，我们已经开发出了一种探针，用于使用正电子发射断层扫描技术估计这些组织中这些转运蛋白的活性。筛选了几种11 C标记的马尿酸酯衍生物，期望它们会在目标组织中原位水解形成相应的11 C标记的有机酸。在所筛选的化合物中，[ 11 C]马尿酸苄酯在小鼠的目标组织中显示出良好的水解速率和摄取特性。随后使用转运蛋白敲除小鼠进行的评估显示，OAt3的大脑和心脏保留了放射性。– / –和Mrp4 – / –小鼠分别与静脉注射苄基[ 11 C]马尿酸酯后与对照组相比。因此，[ 11 C]马尿酸苄酯可用作分别评估小鼠脑和心脏中OAT3和MRP4活性的探针。