生物素连接的同色胺衍生物：人血清素转运体（hSERT）的高亲和力探针。
Biotin tethered homotryptamine derivatives: high affinity probes of the human serotonin transporter (hSERT).
机构信息
The Department of Chemistry, Vanderbilt University, Nashville, TN 37235-1822, USA.
出版信息
Bioorg Med Chem Lett. 2011 Mar 15;21(6):1678-82. doi: 10.1016/j.bmcl.2011.01.102. Epub 2011 Feb 2.
Abstract
Quantum dot conjugates of compounds capable of inhibiting the serotonin transporter (SERT) could form the basis of fluorescent probes for live cell imaging of membrane bound SERT. Additionally, quantum dot-SERT antagonist conjugates may be amenable to fluorescence-based, high-throughput assays for this transporter. This Letter describes the synthesis of SERT-selective ligands amenable to conjugation to quantum dots via a biotin-streptavidin binding interaction. SERT selectivity and affinity were incorporated into the ligand via a tetrahydropyridine or cyclohexylamine derivative and the affinity of these compounds for SERT was measured by their ability to produce SERT-dependent currents in Xenopus laveis oocytes.
摘要
能够抑制血清素转运体 (SERT) 的化合物的量子点缀合物可以作为荧光探针的基础，用于活细胞中膜结合 SERT 的成像。此外，量子点-SERT 拮抗剂缀合物可能适用于基于荧光的 SERT 高吞吐量测定。本信描述了可通过生物素-链霉亲和素结合相互作用连接到量子点的 SERT 选择性配体的合成。SERT 选择性和亲和力通过四氢吡啶或环己胺衍生物整合到配体中，这些化合物对 SERT 的亲和力通过它们在非洲爪蟾卵母细胞中产生 SERT 依赖性电流的能力来测量。
相似文献
1
Biotin tethered homotryptamine derivatives: high affinity probes of the human serotonin transporter (hSERT).生物素连接的同色胺衍生物：人血清素转运体（hSERT）的高亲和力探针。
Bioorg Med Chem Lett. 2011 Mar 15;21(6):1678-82. doi: 10.1016/j.bmcl.2011.01.102. Epub 2011 Feb 2.
2
A fluorescence displacement assay for antidepressant drug discovery based on ligand-conjugated quantum dots.基于配体偶联量子点的抗抑郁药物发现荧光置换 assay。
J Am Chem Soc. 2011 Nov 9;133(44):17528-31. doi: 10.1021/ja204301g. Epub 2011 Oct 17.
3
Dimethyltryptamine and other hallucinogenic tryptamines exhibit substrate behavior at the serotonin uptake transporter and the vesicle monoamine transporter.二甲色胺和其他致幻色胺在血清素摄取转运体和囊泡单胺转运体中表现出底物行为。
J Neural Transm (Vienna). 2009 Dec;116(12):1591-9. doi: 10.1007/s00702-009-0308-8. Epub 2009 Sep 12.
4
A Novel Biotinylated Homotryptamine Derivative for Quantum Dot Imaging of Serotonin Transporter in Live Cells.一种用于活细胞中血清素转运体量子点成像的新型生物素化高色胺衍生物。
Front Cell Neurosci. 2021 Nov 18;15:667044. doi: 10.3389/fncel.2021.667044. eCollection 2021.
5
Inhibitors of the serotonin transporter protein (SERT): the design and synthesis of biotinylated derivatives of 3-(1,2,3,6-tetrahydro-pyridin-4-yl)-1H-indoles. High-affinity serotonergic ligands for conjugation with quantum dots.血清素转运蛋白（SERT）抑制剂：3-(1,2,3,6-四氢吡啶-4-基)-1H-吲哚生物素化衍生物的设计与合成。用于与量子点结合的高亲和力血清素能配体。
Bioorg Med Chem Lett. 2005 Dec 1;15(23):5307-10. doi: 10.1016/j.bmcl.2005.08.030. Epub 2005 Sep 23.
6
Voltage and ionic regulation of human serotonin transporter in Xenopus oocytes.非洲爪蟾卵母细胞中人类血清素转运体的电压和离子调节
Clin Exp Pharmacol Physiol. 2006 Nov;33(11):1088-92. doi: 10.1111/j.1440-1681.2006.04491.x.
7
4-(4-(dimethylamino)phenyl)-1-methylpyridinium (APP+) is a fluorescent substrate for the human serotonin transporter.4-(4-(二甲氨基)苯基)-1-甲基吡啶鎓（APP+）是人血清素转运体的荧光底物。
J Biol Chem. 2012 Mar 16;287(12):8852-63. doi: 10.1074/jbc.M111.267757. Epub 2012 Jan 30.
8
Substrate and Inhibitor-Specific Conformational Changes in the Human Serotonin Transporter Revealed by Voltage-Clamp Fluorometry.电压钳荧光法揭示的人类血清素转运体中底物和抑制剂特异性构象变化
Mol Pharmacol. 2015 Oct;88(4):676-88. doi: 10.1124/mol.115.099911. Epub 2015 Jul 14.
9
Synthesis and characterization of a pegylated derivative of 3-(1,2,3,6-tetrahydro-pyridin-4yl)-1H-indole (IDT199): a high affinity SERT ligand for conjugation to quantum dots.
Bioorg Med Chem Lett. 2007 Oct 15;17(20):5656-60. doi: 10.1016/j.bmcl.2007.07.061. Epub 2007 Aug 21.
10
Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT) Receptor (5-HTR), 5-HTR, 5-HTR, and Serotonin Transporter.取代色胺类药物在 5-羟色胺（5-HT）受体（5-HTR）、5-HTR、5-HTR 和血清素转运体上的药理活性。
J Pharmacol Exp Ther. 2023 Apr;385(1):62-75. doi: 10.1124/jpet.122.001454. Epub 2023 Jan 20.
引用本文的文献
1
A Novel Biotinylated Homotryptamine Derivative for Quantum Dot Imaging of Serotonin Transporter in Live Cells.一种用于活细胞中血清素转运体量子点成像的新型生物素化高色胺衍生物。
Front Cell Neurosci. 2021 Nov 18;15:667044. doi: 10.3389/fncel.2021.667044. eCollection 2021.
2
Single-quantum-dot tracking reveals altered membrane dynamics of an attention-deficit/hyperactivity-disorder-derived dopamine transporter coding variant.单量子点追踪揭示了注意力缺陷多动障碍衍生的多巴胺转运体编码变体的膜动力学改变。
ACS Chem Neurosci. 2015 Apr 15;6(4):526-34. doi: 10.1021/cn500202c. Epub 2015 Mar 16.
3
Quantum dot conjugates of GABA and muscimol: binding to α1β2γ2 and ρ1 GABA(A) receptors.GABA 和 muscimol 的量子点缀合物：与 α1β2γ2 和 ρ1 GABA(A) 受体结合。
ACS Chem Neurosci. 2013 Mar 20;4(3):435-43. doi: 10.1021/cn300144v. Epub 2013 Jan 11.
4
Differential serotonin transport is linked to the rh5-HTTLPR in peripheral blood cells.差异血清素转运与外周血细胞中的 rh5-HTTLPR 相关。
Transl Psychiatry. 2012 Feb 7;2(2):e77. doi: 10.1038/tp.2012.2.
5
A fluorescence displacement assay for antidepressant drug discovery based on ligand-conjugated quantum dots.基于配体偶联量子点的抗抑郁药物发现荧光置换 assay。
J Am Chem Soc. 2011 Nov 9;133(44):17528-31. doi: 10.1021/ja204301g. Epub 2011 Oct 17.
6
Identification of a novel selective serotonin reuptake inhibitor by coupling monoamine transporter-based virtual screening and rational molecular hybridization.通过基于单胺转运蛋白的虚拟筛选与合理的分子杂交相结合鉴定一种新型选择性5-羟色胺再摄取抑制剂
ACS Chem Neurosci. 2011 Jun 8;2(9):544-552. doi: 10.1021/cn200044x.
本文引用的文献
1
Synthesis, Surface Studies, Composition and Structural Characterization of CdSe, Core/Shell, and Biologically Active Nanocrystals.CdSe、核壳结构及生物活性纳米晶体的合成、表面研究、组成与结构表征
Surf Sci Rep. 2007 Apr 30;62(4):111-157. doi: 10.1016/j.surfrep.2007.02.001.
2
Synthesis and characterization of a pegylated derivative of 3-(1,2,3,6-tetrahydro-pyridin-4yl)-1H-indole (IDT199): a high affinity SERT ligand for conjugation to quantum dots.
Bioorg Med Chem Lett. 2007 Oct 15;17(20):5656-60. doi: 10.1016/j.bmcl.2007.07.061. Epub 2007 Aug 21.
3
Conformationally restricted homotryptamines 3. Indole tetrahydropyridines and cyclohexenylamines as selective serotonin reuptake inhibitors.构象受限的高色胺3。吲哚四氢吡啶和环己烯基胺作为选择性5-羟色胺再摄取抑制剂。
Bioorg Med Chem Lett. 2007 Jun 1;17(11):3099-104. doi: 10.1016/j.bmcl.2007.03.040. Epub 2007 Mar 16.
4
Structural basis for near unity quantum yield core/shell nanostructures.接近单位量子产率的核/壳纳米结构的结构基础。
Nano Lett. 2006 Jul;6(7):1496-501. doi: 10.1021/nl060993k.
5
Surface modification to reduce nonspecific binding of quantum dots in live cell assays.用于减少活细胞分析中量子点非特异性结合的表面修饰。
Bioconjug Chem. 2005 Nov-Dec;16(6):1488-94. doi: 10.1021/bc0502006.
6
Inhibitors of the serotonin transporter protein (SERT): the design and synthesis of biotinylated derivatives of 3-(1,2,3,6-tetrahydro-pyridin-4-yl)-1H-indoles. High-affinity serotonergic ligands for conjugation with quantum dots.血清素转运蛋白（SERT）抑制剂：3-(1,2,3,6-四氢吡啶-4-基)-1H-吲哚生物素化衍生物的设计与合成。用于与量子点结合的高亲和力血清素能配体。
Bioorg Med Chem Lett. 2005 Dec 1;15(23):5307-10. doi: 10.1016/j.bmcl.2005.08.030. Epub 2005 Sep 23.
7
Regulated internalization and phosphorylation of the native norepinephrine transporter in response to phorbol esters. Evidence for localization in lipid rafts and lipid raft-mediated internalization.佛波酯刺激下天然去甲肾上腺素转运体的调节性内化与磷酸化。定位于脂筏及脂筏介导的内化的证据。
J Biol Chem. 2004 Apr 30;279(18):19315-26. doi: 10.1074/jbc.M311172200. Epub 2004 Feb 19.
8
Targeting cell surface receptors with ligand-conjugated nanocrystals.用配体偶联纳米晶体靶向细胞表面受体。
J Am Chem Soc. 2002 May 1;124(17):4586-94. doi: 10.1021/ja003486s.
9
Quantum dot bioconjugates for ultrasensitive nonisotopic detection.用于超灵敏非同位素检测的量子点生物共轭物。
Science. 1998 Sep 25;281(5385):2016-8. doi: 10.1126/science.281.5385.2016.
10
Semiconductor nanocrystals as fluorescent biological labels.半导体纳米晶体作为荧光生物标记物。
Science. 1998 Sep 25;281(5385):2013-6. doi: 10.1126/science.281.5385.2013.
Zotero 插件