6-fluoropyridoxol | 42242-41-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-fluoropyridoxol
• 英文别名: 6-fluoro-4,5-bis-hydroxymethyl-2-methyl-pyridin-3-ol；6-fluoro-4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol
• CAS: 42242-41-1
• 化学式: C₈H₁₀FNO₃
• 分子量: 187.171
• InChiKey: IDPINNAOTHGQQW-UHFFFAOYSA-N

物化性质

• 沸点：
  509.4±45.0 °C(Predicted)
• 密度：
  1.448±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  73.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-fluoropyridoxol 在 palladium on activated charcoal 4 A molecular sieve 、 四丁基溴化铵 、 氨 、 氢气 、 氰化汞 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 50.0 ℃ 、172.37 kPa 条件下， 反应 49.0h， 生成 3-O-(β-D-galactopyranosyl)-α⁴,α⁵-di-O-(β-D-glucopyranosyl)-6-fluoropyridoxol
  参考文献：
  名称：

  Synthesis and Characterization of Novel lacZ Gene Reporter Molecules:  Detection of β-Galactosidase Activity by ¹⁹F Nuclear Magnetic Resonance of Polyglycosylated Fluorinated Vitamin B₆

  摘要：

  Gene therapy has emerged as a promising strategy for treatment of various diseases. However, widespread implementation is hampered by difficulties in assessing the success of transfection, in particular, the spatial extent of expression in the target tissue and the longevity of expression. Thus, the development of noninvasive reporter techniques based on appropriate molecules and imaging modalities may help to assay gene expression. We have previously demonstrated the ability to detect beta-galactosidase (beta-gal) activity on the basis of F-19 NMR chemical shift associated with release of fluorophenyl aglycons from galactopyranoside conjugates. Use of fluoropyridoxol as the aglycon provides a potential less toxic alternative and we now report the design, synthesis, and structural analysis of a series of novel polyglycosylated fluorinated vitamin 136 derivatives as F-19 NMR-sensitive aglycons for detection of lacZ gene expression. In particular, we report the activity of 3,alpha(4),alpha(5)-tri-O-(beta-D-galactopyranosyl)-6-fluoropyridoxol 4, 3-O-(beta-D-galactopyranosyl)-alpha(4),alpha(5)-di-O-(beta-D-glucopyranosyl)-6-fluoropyridoxol 12, and 3-O-(beta-D-galactopyranosyl)-alpha(4),alpha(5)-di-O-(alpha-D-mannopyranosyl)-6-fluoropyridoxol 13. Compounds 4, 12, and 13 all show promising characteristics including highly sensitive F-19 NMR response to beta-gal activity (Delta delta = 9.0 similar to 9.4 ppm), minimal toxicity for substrate or aglycon, and good water solubility. However, the differential glycosylation of 12 and 13 appears more advantageous for assessing lacZ gene expression in vivo.

  DOI：

  10.1021/jm051049o
• 作为产物：
  描述：

  6-amino-4,5-bis-hydroxymethyl-2-methyl-pyridin-3-ol 在 氢氟酸 、 sodium nitrite 作用下， 以 吡啶 为溶剂， 以50%的产率得到6-fluoropyridoxol
  参考文献：
  名称：

  Development of novel 19 F NMR pH indicators: synthesis and evaluation of a series of fluorinated vitamin B 6 analogues

  摘要：

  We have synthesized a series of novel fluorinated vitamin B-6 analogues (6-fluoropyridoxol derivatives) as potential F-19 NMR pH indicators for use in vivo. Modifications included addition of aldehyde, carboxyl or aminomethyl groups at the 4- or 5-ring position, and examination of a trifluoromethyl moiety as an internal chemical shift standard. The variation in chemical shift with respect to acid-base titration showed pK(a) values in the range 7.05-9.5 with a chemical shift sensitivity in the range 7.4-12 ppm. Several of the molecules readily cross cell membranes providing estimates of both intra- and extra-cellular pH in whole blood. 6-Fluoropyridoxamine (6-FPAM) exhibits a pK(a) = 7.05, which is closer to normal physiological pH than the parent molecule 6-fluoropyridoxol (6-FPOL) (pK(a) = 8.2), and should thus, be useful for precise and accurate measurements of pH in vivo. Enhanced spectral resolution for 6-FPAM over 6-FPOL is demonstrated in whole blood and the perfused rat heart. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00104-7

文献信息

• Use of particulate contrast agents in diagnostic imaging for studying physiological paramaters
  申请人：Fossheim Lise Sigrid

  公开号：US20050136002A1

  公开（公告）日：2005-06-23

  The present invention relates to a method of imaging of an animate human or non-human animal body, which method comprises: administering parenterally to said body a particulate material comprising a matrix or membrane material and at least one contrast generating species, which matrix or membrane material is responsive to a pre-selected physiological parameter whereby to alter the contrast efficacy of said species in response to a change in the value of said parameter; generating image data of at least part of said body in which said species is present; and generating therefrom a signal indicative of the value or variation of said parameter in said part of said body. The invention also relates to contrast media for imaging a physioloogical parameter.

  本发明涉及一种用于成像活体人类或非人类动物体的方法，该方法包括：将包含基质或膜材料和至少一种对比产生物的颗粒材料经肠外途径注入到该体内，其中所述基质或膜材料对预选生理参数具有响应性，以便在所述参数值发生变化时改变所述物种的对比效能；在存在所述物种的至少一部分体内生成图像数据；并从中生成一个信号，该信号指示所述部位体内所述参数的值或变化。本发明还涉及用于成像生理参数的对比介质。
• USE OF PARTICULATE CONTRAST AGENTS IN DIAGNOSTIC IMAGING FOR STUDYING PHYSIOLOGICAL PARAMATERS
  申请人：Fossheim Sigrid Lise

  公开号：US20090191131A1

  公开（公告）日：2009-07-30

  The present invention relates to a method of imaging of an animate human or non-human animal body, which method comprises: administering parenterally to said body a particulate material comprising a matrix or membrane material and at least one contrast generating species, which matrix or membrane material is responsive to a pre-selected physiological parameter whereby to alter the contrast efficacy of said species in response to a change in the value of said parameter; generating image data of at least part of said body in which said species is present; and generating therefrom a signal indicative of the value or variation of said parameter in said part of said body. The invention also relates to contrast media for imaging a physiological parameter.

  本发明涉及一种成像动物或非人类动物体的方法，该方法包括：将包含基质或膜材料和至少一种对比剂的颗粒状物质经肠外给予该体，该基质或膜材料对预选生理参数具有响应性，以便在该参数值发生变化时改变该对比剂的对比效果；生成至少该体的部分中存在该对比剂的图像数据；并由此生成一个信号，指示该体部分中该参数的值或变化。本发明还涉及用于成像生理参数的对比介质。
• Chemistry and biology of vitamin B6. 31. Synthesis and physicochemical and biological properties of 6-halogen-substituted vitamin B6 analogs
  作者：W. Korytnyk、S. C. Srivastava

  DOI：10.1021/jm00264a013

  日期：1973.6
• USE OF PARTICULATE CONTRAST AGENTS IN DIAGNOSTIC IMAGING FOR STUDYING PHYSIOLOGICAL PARAMETERS
  申请人：NYCOMED IMAGING AS

  公开号：EP1069888A1

  公开（公告）日：2001-01-24
• Transporter-targeted methods of diagnosis and treatment
  申请人：Zerangue Noa

  公开号：US20070231260A1

  公开（公告）日：2007-10-04

  Methods of treating a disease in a patient, methods of determining the presence of a disease in a patient, methods of determining whether a disease in a patient is suitable to be treated with a therapeutic agent, and methods of monitoring treatment of a disease in a patient comprising determining a level of expression of a transporter in cells of a tissue associated with the disease are disclosed. The methods include administering to a patient a diagnostic conjugate and/or therapeutic conjugate that are substrates for a transporter expressed by cells of a tissue associated with the disease. Kits comprising a diagnostic composition comprising a diagnostic conjugate that is a transporter substrate are also disclosed. In particular, methods and kits useful for diagnosing and treating cancer are disclosed.