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Literature DB >> 18595692

A highly sensitive fluorogenic probe for cytochrome P450 activity in live cells.

Melissa M Yatzeck¹, Luke D Lavis, Tzu-Yuan Chao, Sunil S Chandran, Ronald T Raines.

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.

Entities: Chemical Gene

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Year: 2008 PMID： 18595692 PMCID： PMC2586036 DOI： 10.1016/j.bmcl.2008.06.015

Source DB: PubMed Journal: Bioorg Med Chem Lett ISSN： 0960-894X Impact factor: 2.823

37 in total

1. Lung carcinogenesis: resveratrol modulates the expression of genes involved in the metabolism of PAH in human bronchial epithelial cells.

Authors: S Mollerup; S Ovrebø; A Haugen
Journal: Int J Cancer Date: 2001-04-01 Impact factor: 7.396

2. Fluorogenic label for biomolecular imaging.

Authors: Luke D Lavis; Tzu-Yuan Chao; Ronald T Raines
Journal: ACS Chem Biol Date: 2006-05-23 Impact factor: 5.100

3. Cytotoxic ribonucleases: the dichotomy of Coulombic forces.

Authors: R Jeremy Johnson; Tzu-Yuan Chao; Luke D Lavis; Ronald T Raines
Journal: Biochemistry Date: 2007-08-18 Impact factor: 3.162

Review 4. Cytochromes P450: decision-making tools for personalized therapeutics.

Authors: Michael Murray; Nenad Petrovic
Journal: Curr Opin Mol Ther Date: 2006-12

5. A real-time fluorescence assay for measuring N-dealkylation.

Authors: Richard T Mayer; E Kurt Dolence; Gabriele E Mayer
Journal: Drug Metab Dispos Date: 2006-10-11 Impact factor: 3.922

6. Induction and regulation of xenobiotic-metabolizing cytochrome P450s in the human A549 lung adenocarcinoma cell line.

Authors: J Hukkanen; A Lassila; K Päivärinta; S Valanne; S Sarpo; J Hakkola; O Pelkonen; H Raunio
Journal: Am J Respir Cell Mol Biol Date: 2000-03 Impact factor: 6.914

Review 7. The role of cytochrome P450 enzymes in endogenous signalling pathways and environmental carcinogenesis.

Authors: Daniel W Nebert; Timothy P Dalton
Journal: Nat Rev Cancer Date: 2006-12 Impact factor: 60.716

8. Characterization of substrate binding to cytochrome P450 1A1 using molecular modeling and kinetic analyses: case of residue 382.

Authors: Jianguo Liu; Spencer S Ericksen; Dan Besspiata; Charles W Fisher; Grazyna D Szklarz
Journal: Drug Metab Dispos Date: 2003-04 Impact factor: 3.922

9. Rapid determination of enzyme activities of recombinant human cytochromes P450, human liver microsomes and hepatocytes.

Authors: Anima Ghosal; Neil Hapangama; Yuan Yuan; Xiaowen Lu; Debra Horne; James E Patrick; Shmuel Zbaida
Journal: Biopharm Drug Dispos Date: 2003-12 Impact factor: 1.627

9. Masked Amino Trimethyl Lock (H₂ N-TML) Systems: New Molecular Entities for the Development of Turn-On Fluorophores and Their Application in Hydrogen Sulfide (H₂ S) Imaging in Human Cells.

Authors: Claire Cheyenne Jimidar; Jörg Grunenberg; Bianka Karge; Hazel Leanne Sarah Fuchs; Mark Brönstrup; Philipp Klahn
Journal: Chemistry Date: 2021-11-08 Impact factor: 5.020

9 in total

A highly sensitive fluorogenic probe for cytochrome P450 activity in live cells.

1. Lung carcinogenesis: resveratrol modulates the expression of genes involved in the metabolism of PAH in human bronchial epithelial cells.

2. Fluorogenic label for biomolecular imaging.

3. Cytotoxic ribonucleases: the dichotomy of Coulombic forces.

Review 4. Cytochromes P450: decision-making tools for personalized therapeutics.

5. A real-time fluorescence assay for measuring N-dealkylation.

6. Induction and regulation of xenobiotic-metabolizing cytochrome P450s in the human A549 lung adenocarcinoma cell line.

Review 7. The role of cytochrome P450 enzymes in endogenous signalling pathways and environmental carcinogenesis.

8. Characterization of substrate binding to cytochrome P450 1A1 using molecular modeling and kinetic analyses: case of residue 382.

9. Rapid determination of enzyme activities of recombinant human cytochromes P450, human liver microsomes and hepatocytes.

Review 10. Inhibition of cytochromes p450: existing and new promising therapeutic targets.

1. Sensitive fluorogenic substrate for alkaline phosphatase.

2. Electronic and Steric Optimization of Fluorogenic Probes for Biomolecular Imaging.

3. Synthesis and utility of fluorogenic acetoxymethyl ethers.

4. Fluorogenic affinity label for the facile, rapid imaging of proteins in live cells.

Review 5. Visualizing and Manipulating Biological Processes by Using HaloTag and SNAP-Tag Technologies.

6. Activatable Optical Probes for the Detection of Enzymes.

7. Trimethyl lock: A trigger for molecular release in chemistry, biology, and pharmacology.

8. Label-free chemical imaging of cytochrome P450 activity by Raman microscopy.

9. Masked Amino Trimethyl Lock (H₂ N-TML) Systems: New Molecular Entities for the Development of Turn-On Fluorophores and Their Application in Hydrogen Sulfide (H₂ S) Imaging in Human Cells.