一种用于活细胞中细胞色素P450活性的高灵敏度荧光探针。
A highly sensitive fluorogenic probe for cytochrome P450 activity in live cells.
作者信息
Yatzeck Melissa M, Lavis Luke D, Chao Tzu-Yuan, Chandran Sunil S, Raines Ronald T
机构信息
Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706-1322, USA.
出版信息
Bioorg Med Chem Lett. 2008 Nov 15;18(22):5864-6. doi: 10.1016/j.bmcl.2008.06.015. Epub 2008 Jun 10.
Abstract
A derivative of rhodamine 110 has been designed and assessed as a probe for cytochrome P450 activity. This probe is the first to utilize a 'trimethyl lock' that is triggered by cleavage of an ether bond. In vitro, fluorescence was manifested by the CYP1A1 isozyme with k(cat)/K(M)=8.8x10(3)M(-1)s(-1) and K(M)=0.09microM. In cellulo, the probe revealed the induction of cytochrome P450 activity by the carcinogen 2,3,7,8-tetrachlorodibenzo-p-dioxin, and its repression by the chemoprotectant resveratrol.
摘要
一种罗丹明110衍生物已被设计并评估为细胞色素P450活性的探针。该探针是首个利用由醚键裂解触发的“三甲基锁”的探针。在体外，CYP1A1同工酶表现出荧光，其催化常数与米氏常数之比（k(cat)/K(M)）为8.8×10³M⁻¹s⁻¹，米氏常数（K(M)）为0.09微摩尔。在细胞内，该探针揭示了致癌物2,3,7,8 - 四氯二苯并 - p - 二恶英对细胞色素P450活性的诱导作用，以及化学保护剂白藜芦醇对其的抑制作用。
相似文献
1
A highly sensitive fluorogenic probe for cytochrome P450 activity in live cells.一种用于活细胞中细胞色素P450活性的高灵敏度荧光探针。
Bioorg Med Chem Lett. 2008 Nov 15;18(22):5864-6. doi: 10.1016/j.bmcl.2008.06.015. Epub 2008 Jun 10.
2
Resveratrol inhibits TCDD-induced expression of CYP1A1 and CYP1B1 and catechol estrogen-mediated oxidative DNA damage in cultured human mammary epithelial cells.白藜芦醇可抑制2,3,7,8-四氯二苯并对二恶英诱导的CYP1A1和CYP1B1的表达以及儿茶酚雌激素介导的培养人乳腺上皮细胞中的氧化性DNA损伤。
Carcinogenesis. 2004 Oct;25(10):2005-13. doi: 10.1093/carcin/bgh183. Epub 2004 May 13.
3
Resveratrol inhibits transcription of CYP1A1 in vitro by preventing activation of the aryl hydrocarbon receptor.白藜芦醇通过阻止芳烃受体的激活在体外抑制CYP1A1的转录。
Cancer Res. 1998 Dec 15;58(24):5707-12.
4
Roles of coactivator proteins in dioxin induction of CYP1A1 and CYP1B1 in human breast cancer cells.共激活蛋白在二噁英诱导人乳腺癌细胞中CYP1A1和CYP1B1表达中的作用
Toxicol Sci. 2009 Jan;107(1):1-8. doi: 10.1093/toxsci/kfn217. Epub 2008 Oct 8.
5
Regulation of cytochrome P450 in a primary culture of rainbow trout hepatocytes.虹鳟鱼肝细胞原代培养中细胞色素P450的调控
In Vitro Cell Dev Biol Anim. 2001 Mar;37(3):180-4. doi: 10.1290/1071-2690(2001)037<0180:ROCPIA>2.0.CO;2.
6
Strong synergistic induction of CYP1A1 expression by andrographolide plus typical CYP1A inducers in mouse hepatocytes.
Toxicol Appl Pharmacol. 2007 Oct 15;224(2):156-62. doi: 10.1016/j.taap.2007.07.008. Epub 2007 Jul 28.
7
2,3,7,8-Tetrachlorodibenzo-p-dioxin and diindolylmethanes differentially induce cytochrome P450 1A1, 1B1, and 19 in H295R human adrenocortical carcinoma cells.2,3,7,8-四氯二苯并对二恶英和二吲哚甲烷对H295R人肾上腺皮质癌细胞中细胞色素P450 1A1、1B1和19的诱导作用存在差异。
Toxicol Sci. 2001 May;61(1):40-8. doi: 10.1093/toxsci/61.1.40.
8
Effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin or 2,2',4,4',5,5'-hexachlorobiphenyl on vitamin K-dependent blood coagulation in male and female WAG/Rij-rats.2,3,7,8-四氯二苯并对二恶英或2,2',4,4',5,5'-六氯联苯对雄性和雌性WAG/Rij大鼠维生素K依赖的血液凝固的影响。
Chemosphere. 1999 Feb;38(3):489-505. doi: 10.1016/s0045-6535(98)00208-2.
9
The human cytochrome P450 1A1 mRNA is rapidly degraded in HepG2 cells.人类细胞色素P450 1A1信使核糖核酸在肝癌细胞系HepG2细胞中迅速降解。
Arch Biochem Biophys. 2000 Dec 15;384(2):311-8. doi: 10.1006/abbi.2000.2115.
10
Evidence for an aryl hydrocarbon receptor-mediated cytochrome p450 autoregulatory pathway.芳烃受体介导的细胞色素P450自身调节途径的证据。
Mol Pharmacol. 2007 Nov;72(5):1369-79. doi: 10.1124/mol.107.038968. Epub 2007 Aug 24.
引用本文的文献
1
Robust Inclusion Complex of Topotecan Comprised within a Rhodamine-Labeled β-Cyclodextrin: Competing Proton and Energy Transfer Processes.包含在罗丹明标记的β-环糊精中的拓扑替康的稳健包合物：竞争性质子和能量转移过程
Pharmaceutics. 2023 May 30;15(6):1620. doi: 10.3390/pharmaceutics15061620.
2
Label-free chemical imaging of cytochrome P450 activity by Raman microscopy.拉曼显微镜无标记化学成像细胞色素 P450 活性。
Commun Biol. 2022 Aug 22;5(1):778. doi: 10.1038/s42003-022-03713-1.
3
Masked Amino Trimethyl Lock (H N-TML) Systems: New Molecular Entities for the Development of Turn-On Fluorophores and Their Application in Hydrogen Sulfide (H S) Imaging in Human Cells.掩蔽氨基三甲基锁 (H N-TML) 系统：用于开发开启型荧光团的新分子实体及其在人细胞中硫化氢 (H S) 成像中的应用。
Chemistry. 2022 Jan 10;28(2):e202103525. doi: 10.1002/chem.202103525. Epub 2021 Nov 8.
4
Visualizing and Manipulating Biological Processes by Using HaloTag and SNAP-Tag Technologies.利用 HaloTag 和 SNAP-Tag 技术可视化和操作生物过程。
Chembiochem. 2020 Jul 16;21(14):1935-1946. doi: 10.1002/cbic.202000037. Epub 2020 Apr 2.
5
Electronic and Steric Optimization of Fluorogenic Probes for Biomolecular Imaging.用于生物分子成像的荧光探针的电子和空间优化。
J Org Chem. 2017 Apr 21;82(8):4297-4304. doi: 10.1021/acs.joc.7b00285. Epub 2017 Apr 11.
6
Activatable Optical Probes for the Detection of Enzymes.用于酶检测的可激活光学探针。
Curr Org Synth. 2011 Aug;8(4):498-520. doi: 10.2174/157017911796117232.
7
Trimethyl lock: A trigger for molecular release in chemistry, biology, and pharmacology.三甲基锁：化学、生物学和药理学中分子释放的触发因素。
Chem Sci. 2012 Jan 1;3(8):2412-2420. doi: 10.1039/C2SC20536J. Epub 2012 May 30.
8
Sensitive fluorogenic substrate for alkaline phosphatase.用于碱性磷酸酶的灵敏荧光底物。
Anal Biochem. 2011 Nov 15;418(2):247-52. doi: 10.1016/j.ab.2011.07.021. Epub 2011 Jul 24.
9
Synthesis and utility of fluorogenic acetoxymethyl ethers.荧光乙酰氧基甲基醚的合成与应用
Chem Sci. 2011 Jan 1;2(3):521-530. doi: 10.1039/C0SC00466A.
10
Fluorogenic affinity label for the facile, rapid imaging of proteins in live cells.用于活细胞中蛋白质简便、快速成像的荧光亲和标记物。
Org Biomol Chem. 2009 Oct 7;7(19):3969-75. doi: 10.1039/b907664f. Epub 2009 Jul 31.
本文引用的文献
1
Synthesis of fluorogenic polymers for visualizing cellular internalization.用于可视化细胞内吞作用的荧光聚合物的合成。
Org Lett. 2008 Jul 17;10(14):2997-3000. doi: 10.1021/ol800932w. Epub 2008 Jun 19.
2
Bright ideas for chemical biology.化学生物学的绝妙想法。
ACS Chem Biol. 2008 Mar 20;3(3):142-55. doi: 10.1021/cb700248m.
3
Trimethyl lock: a stable chromogenic substrate for esterases.三甲基锁：一种用于酯酶的稳定显色底物。
Molecules. 2008 Jan 31;13(2):204-11. doi: 10.3390/molecules13020204.
4
Development of sensitive cathepsin G fluorogenic substrate using combinatorial chemistry methods.运用组合化学方法开发灵敏的组织蛋白酶G荧光底物。
Anal Biochem. 2008 Apr 15;375(2):306-12. doi: 10.1016/j.ab.2008.01.020. Epub 2008 Jan 19.
5
Cytochrome P450 inactivation by pharmaceuticals and phytochemicals: therapeutic relevance.药物和植物化学物质对细胞色素P450的失活作用：治疗相关性。
Drug Metab Rev. 2008;40(1):101-47. doi: 10.1080/03602530701836704.
6
Cytochrome p450 and chemical toxicology.细胞色素P450与化学毒理学
Chem Res Toxicol. 2008 Jan;21(1):70-83. doi: 10.1021/tx700079z. Epub 2007 Dec 6.
7
Influence of cytochrome P450 polymorphisms on drug therapies: pharmacogenetic, pharmacoepigenetic and clinical aspects.细胞色素P450基因多态性对药物治疗的影响：药物遗传学、药物表观遗传学及临床方面
Pharmacol Ther. 2007 Dec;116(3):496-526. doi: 10.1016/j.pharmthera.2007.09.004. Epub 2007 Oct 9.
8
Chemical proteomic probes for profiling cytochrome p450 activities and drug interactions in vivo.用于体内细胞色素P450活性分析及药物相互作用研究的化学蛋白质组学探针。
Chem Biol. 2007 Sep;14(9):1043-51. doi: 10.1016/j.chembiol.2007.08.008.
9
Inhibition of cytochromes p450: existing and new promising therapeutic targets.
Drug Metab Rev. 2007;39(2-3):481-99. doi: 10.1080/03602530701498455.
10
Cytotoxic ribonucleases: the dichotomy of Coulombic forces.细胞毒性核糖核酸酶：库仑力的二分法
Biochemistry. 2007 Sep 11;46(36):10308-16. doi: 10.1021/bi700857u. Epub 2007 Aug 18.
Zotero 插件