6-三氟甲基吡啶醇：用于体内检测的新型（19）F NMR pH 指示剂。
6-Trifluoromethylpyridoxine: novel (19)F NMR pH indicator for in vivo detection.
机构信息
Advanced Radiological Sciences, Department of Radiology, The University of Texas Southwestern Medical Center at Dallas , 5323 Harry Hines Boulevard, Dallas, Texas 75390-9058, United States.
出版信息
J Med Chem. 2012 Aug 9;55(15):6814-21. doi: 10.1021/jm300520q. Epub 2012 Jul 27.
Abstract
pH plays an important role in tumor proliferation, angiogenesis, metabolic control, and the efficacy of cytotoxic therapy, and accurate noninvasive assessment of tumor pH promises to provide insight into developmental processes and prognostic information. In this paper, we report the design, synthesis, and characterization of two novel pH indicators 6-trifluoromethylpyridoxine 8 and α(4),α(5)-di-O-[3'-O-(β-d-glucopyranosyl)propyl]-6-trifluoromethylpyridoxine 17 and demonstrate 8 as an extracellular (19)F NMR pH probe to assess pH(e) of various tumors in vivo.
摘要
pH 在肿瘤增殖、血管生成、代谢控制和细胞毒性治疗的疗效中起着重要作用，准确的无创评估肿瘤 pH 值有望提供对发育过程和预后信息的深入了解。在本文中，我们报告了两种新型 pH 指示剂 6-三氟甲基吡哆醇 8 和 α(4),α(5)-二-O-[3'-O-(β-d-吡喃葡萄糖基)丙基]-6-三氟甲基吡哆醇 17 的设计、合成和表征，并证明 8 作为一种细胞外 (19)F NMR pH 探针，可用于评估体内各种肿瘤的 pH(e)。
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本文引用的文献
1
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Chempluschem. 2012 May 1;77(5):370-378. doi: 10.1002/cplu.201100072.
2
Imaging pH and metastasis.成像 pH 值与转移。
NMR Biomed. 2011 Jul;24(6):582-91. doi: 10.1002/nbm.1644. Epub 2011 Mar 8.
3
Tumor pH and its measurement.肿瘤 pH 值及其测量。
J Nucl Med. 2010 Aug;51(8):1167-70. doi: 10.2967/jnumed.109.068981. Epub 2010 Jul 21.
4
Acidic extracellular pH promotes experimental metastasis of human melanoma cells in athymic nude mice.酸性细胞外pH值促进人黑色素瘤细胞在无胸腺裸鼠体内的实验性转移。
Cancer Res. 2006 Jul 1;66(13):6699-707. doi: 10.1158/0008-5472.CAN-06-0983.
5
Tumor pH controls the in vivo efficacy of weak acid and base chemotherapeutics.肿瘤pH值控制弱酸和弱碱化疗药物的体内疗效。
Mol Cancer Ther. 2006 May;5(5):1275-9. doi: 10.1158/1535-7163.MCT-06-0024.
6
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J Med Chem. 2006 Mar 23;49(6):1991-9. doi: 10.1021/jm051049o.
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