揭示细胞色素P450结合作用：CYP17A1的钌（II）笼形抑制剂
Illuminating cytochrome P450 binding: Ru(ii)-caged inhibitors of CYP17A1.
作者信息
Li Ao, Yadav Rahul, White Jessica K, Herroon Mackenzie K, Callahan Brian P, Podgorski Izabela, Turro Claudia, Scott Emily E, Kodanko Jeremy J
机构信息
Department of Chemistry, Wayne State University, Detroit, MI 48202, USA.
Department of Medicinal Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
出版信息
Chem Commun (Camb). 2017 Mar 28;53(26):3673-3676. doi: 10.1039/c7cc01459g.
Abstract
New Ru(ii)-caged abiraterone complexes were synthesized that exhibit strong absorption in the visible region and release the steroidal CYP17A1 inhibitor abiraterone upon exposure to low energy visible light in buffer and prostate cancer cells. Photoinduced release results in abiraterone binding to its CYP17A1 target in an inhibitory mode.
摘要
合成了新型钌（II）-笼状阿比特龙配合物，其在可见光区域表现出强烈吸收，并在缓冲液和前列腺癌细胞中暴露于低能量可见光时释放甾体CYP17A1抑制剂阿比特龙。光诱导释放导致阿比特龙以抑制模式与其CYP17A1靶点结合。
相似文献
1
Illuminating cytochrome P450 binding: Ru(ii)-caged inhibitors of CYP17A1.
Chem Commun (Camb). 2017 Mar 28;53(26):3673-3676. doi: 10.1039/c7cc01459g.
2
Photosensitive Ru(II) Complexes as Inhibitors of the Major Human Drug Metabolizing Enzyme CYP3A4.
J Am Chem Soc. 2021 Jun 23;143(24):9191-9205. doi: 10.1021/jacs.1c04155. Epub 2021 Jun 10.
3
Cytotoxic Ruthenium(II) Complexes Containing a Dangling Pyridine: Selectivity for Diseased Cells Mediated by pH-Dependent DNA Binding.
Inorg Chem. 2022 Feb 14;61(6):2864-2882. doi: 10.1021/acs.inorgchem.1c03399. Epub 2022 Jan 31.
4
Half-Sandwich Iridium(III) and Ruthenium(II) Complexes Containing P^P-Chelating Ligands: A New Class of Potent Anticancer Agents with Unusual Redox Features.
Inorg Chem. 2018 Feb 19;57(4):1705-1716. doi: 10.1021/acs.inorgchem.7b01959. Epub 2018 Feb 5.
5
New Class of Half-Sandwich Ruthenium(II) Arene Complexes Bearing the Water-Soluble CAP Ligand as an in Vitro Anticancer Agent.
Inorg Chem. 2017 May 15;56(10):5514-5518. doi: 10.1021/acs.inorgchem.7b00915. Epub 2017 Apr 26.
6
Pyrazole appended quinoline-BODIPY based arene ruthenium complexes: their anticancer activity and potential applications in cellular imaging.
Dalton Trans. 2018 Dec 11;47(48):17500-17514. doi: 10.1039/c8dt02947d.
7
A Cancer Cell-Selective and Low-Toxic Bifunctional Heterodinuclear Pt(IV)-Ru(II) Anticancer Prodrug.
Inorg Chem. 2018 Mar 5;57(5):2917-2924. doi: 10.1021/acs.inorgchem.8b00053. Epub 2018 Feb 13.
8
Novel oxazolinyl derivatives of pregna-5,17(20)-diene as 17α-hydroxylase/17,20-lyase (CYP17A1) inhibitors.
Steroids. 2014 Oct;88:66-71. doi: 10.1016/j.steroids.2014.06.014. Epub 2014 Jun 24.
9
A nuclear permeable Ru(ii)-based photoactivated chemotherapeutic agent towards a series of cancer cells: in vitro and in vivo studies.
Dalton Trans. 2019 May 15;48(19):6492-6500. doi: 10.1039/c9dt00441f.
10
Rhodamine-modified fluorescent half-sandwich iridium and ruthenium complexes: potential application as bioimaging and anticancer agents.
Dalton Trans. 2019 Apr 9;48(15):4788-4793. doi: 10.1039/c9dt00999j.
引用本文的文献
1
Control of metalloenzyme activity using photopharmacophores.
Coord Chem Rev. 2024 Jan 15;499. doi: 10.1016/j.ccr.2023.215485. Epub 2023 Oct 31.
2
Mixed Ru(II)-Ir(III) Complexes as Photoactive Inhibitors of the Major Human Drug Metabolizing Enzyme CYP3A4.
Inorg Chem. 2024 Oct 7;63(40):18509-18518. doi: 10.1021/acs.inorgchem.4c02633. Epub 2024 Sep 16.
3
Ru(II) Oligothienyl Complexes with Fluorinated Ligands: Photophysical, Electrochemical, and Photobiological Properties.
Inorg Chem. 2024 May 27;63(21):9735-9752. doi: 10.1021/acs.inorgchem.3c04382. Epub 2024 May 10.
4
The Impact of Inorganic Systems and Photoactive Metal Compounds on Cytochrome P450 Enzymes and Metabolism: From Induction to Inhibition.
Biomolecules. 2024 Apr 4;14(4):441. doi: 10.3390/biom14040441.
5
Ru(II) Phenanthroline-Based Oligothienyl Complexes as Phototherapy Agents.
Inorg Chem. 2023 Dec 25;62(51):21181-21200. doi: 10.1021/acs.inorgchem.3c03216. Epub 2023 Dec 11.
6
Taking phototherapeutics from concept to clinical launch.
Nat Rev Chem. 2021 Nov;5(11):816-834. doi: 10.1038/s41570-021-00326-w. Epub 2021 Oct 6.
7
Low-Temperature Observation of the Excited-State Decay of Ruthenium-(Mono-2,2':6',2″-Terpyridine) Ions with Innocent Ligands: DFT Modeling of an MLCT-MC Intersystem Crossing Pathway.
ACS Omega. 2023 Mar 13;8(12):11623-11633. doi: 10.1021/acsomega.3c01006. eCollection 2023 Mar 28.
8
Ru(II) photocages enable precise control over enzyme activity with red light.
Nat Commun. 2022 Jun 25;13(1):3636. doi: 10.1038/s41467-022-31269-5.
9
Intraligand Excited States Turn a Ruthenium Oligothiophene Complex into a Light-Triggered Ubertoxin with Anticancer Effects in Extreme Hypoxia.
J Am Chem Soc. 2022 May 11;144(18):8317-8336. doi: 10.1021/jacs.2c02475. Epub 2022 Apr 28.
10
Photocytotoxicity and photoinduced phosphine ligand exchange in a Ru(ii) polypyridyl complex.
Chem Sci. 2022 Feb 1;13(7):1933-1945. doi: 10.1039/d1sc05647f. eCollection 2022 Feb 16.
本文引用的文献
1
Combination of Ru(ii) complexes and light: new frontiers in cancer therapy.
Chem Sci. 2015 May 1;6(5):2660-2686. doi: 10.1039/c4sc03759f. Epub 2015 Jan 13.
2
Control of an Unusual Photo-Claisen Rearrangement in Coumarin Caged Tamoxifen through an Extended Spacer.
ACS Chem Biol. 2017 Apr 21;12(4):1001-1010. doi: 10.1021/acschembio.6b00999. Epub 2017 Feb 17.
3
Ruthenium-containing P450 inhibitors for dual enzyme inhibition and DNA damage.
Dalton Trans. 2017 Feb 14;46(7):2165-2173. doi: 10.1039/c6dt04405k.
4
An Overview Of Photosubstitution Reactions Of Ru(II) Imine Complexes And Their Application In Photobiology And Photodynamic Therapy.
Inorganica Chim Acta. 2017 Jan 1;454:7-20. doi: 10.1016/j.ica.2016.06.007. Epub 2016 Jun 18.
5
Hedgehog Proteins Consume Steroidal CYP17A1 Antagonists: Potential Therapeutic Significance in Advanced Prostate Cancer.
ChemMedChem. 2016 Sep 20;11(18):1983-6. doi: 10.1002/cmdc.201600238. Epub 2016 Jul 20.
6
Selective Release of Aromatic Heterocycles from Ruthenium Tris(2-pyridylmethyl)amine with Visible Light.
Inorg Chem. 2016 Jan 4;55(1):10-2. doi: 10.1021/acs.inorgchem.5b02600. Epub 2015 Dec 15.
7
A luminescent ruthenium(II) complex for light-triggered drug release and live cell imaging.
Chem Commun (Camb). 2015 Sep 25;51(74):14038-41. doi: 10.1039/c5cc05172j.
8
New Ru(II) complexes for dual photoreactivity: ligand exchange and (1)O2 generation.
Acc Chem Res. 2015 Aug 18;48(8):2280-7. doi: 10.1021/acs.accounts.5b00227. Epub 2015 Jul 17.
9
Conversion of abiraterone to D4A drives anti-tumour activity in prostate cancer.
Nature. 2015 Jul 16;523(7560):347-51. doi: 10.1038/nature14406. Epub 2015 Jun 1.
10
Synthetic peptides caged on histidine residues with a bisbipyridyl ruthenium(II) complex that can be photolyzed by visible light.
Chem Commun (Camb). 2015 Mar 28;51(25):5501-4. doi: 10.1039/c4cc08049a.
Zotero 插件