Use of a Coumarin-Labeled Hexa-Arginine Peptide as a Fluorescent Hydroxyl Radical Probe in a Nanoparticulate Plasmid DNA Condensate
Abstract

Coumarin derivatives have found application as probes for the hydroxyl radical because one of the products of the reaction between them is a highly fluorescent umbelliferone. We have examined the interaction in aqueous solution between a cationic coumarin-labeled hexa-arginine peptide ligand and plasmid DNA, and compared after gamma irradiation the yields of products derived from both of them. At low ionic strengths, the ligand binds very tightly to the plasmid. Compared with the structurally similar 4-methylumbelliferone (phenolic pKa = 7.8), the fluorescent product derived from gamma irradiation of the coumarin labeled cationic peptide is significantly more acidic (pKa = 6.1), making it a very convenient probe for solutions of pH in the physiological range. The yield of this product is generally in excellent agreement over a wide range of conditions with that of the single strand break product produced by the reaction of the hydroxyl radical with the plasmid. Thus coumarin-labeled peptide ligands offer promise as hydroxyl radical probes for locations in close proximity to DNA.
Cited By
This article is cited by 17 publications.
- Christopher C. Perry, José Ramos-Méndez, Jamie R. Milligan. Boronated Condensed DNA as a Heterochromatic Radiation Target Model. Biomacromolecules 2021, 22 (4) , 1675-1684. https://doi.org/10.1021/acs.biomac.1c00106
- Na Young Lim, Junho Ahn, Miae Won, Wonjin Choi, Jong Seung Kim, Jong Hwa Jung. Novel Cyanostilbene-Based Fluorescent Chemoprobe for Hydroxyl Radicals and Its Two-Photon Bioimaging in Living Cells. ACS Applied Bio Materials 2019, 2 (2) , 936-942. https://doi.org/10.1021/acsabm.8b00796
- Lingyu Zeng, Tian Xia, Wei Hu, Shiyu Chen, Siyu Chi, Yidi Lei, and Zhihong Liu . Visualizing the Regulation of Hydroxyl Radical Level by Superoxide Dismutase via a Specific Molecular Probe. Analytical Chemistry 2018, 90 (2) , 1317-1324. https://doi.org/10.1021/acs.analchem.7b04191
- Xiaohua Li, Xinghui Gao, Wen Shi, and Huimin Ma . Design Strategies for Water-Soluble Small Molecular Chromogenic and Fluorogenic Probes. Chemical Reviews 2014, 114 (1) , 590-659. https://doi.org/10.1021/cr300508p
- Yuming Yang, Qiang Zhao, Wei Feng, and Fuyou Li . Luminescent Chemodosimeters for Bioimaging. Chemical Reviews 2013, 113 (1) , 192-270. https://doi.org/10.1021/cr2004103
- Wei Wei, Jiaqi Pan, Chanan Euaruksakul, Yang Yang, Yi Cui, Qiang Fu, Xinhe Bao. Dynamic observation of in-plane h-BN/graphene heterostructures growth on Ni(111). Nano Research 2020, 13 (7) , 1789-1794. https://doi.org/10.1007/s12274-020-2638-7
- Chris C. Perry, Jose Ramos-Méndez, Jamie R. Milligan. DNA condensation with a boron-containing cationic peptide for modeling boron neutron capture therapy. Radiation Physics and Chemistry 2020, 166 , 108521. https://doi.org/10.1016/j.radphyschem.2019.108521
- Peter Sandwall, Brandt Bastow, Henry Spitz, Howard Elson, Michael Lamba, William Connick, Henry Fenichel. Radio-Fluorogenic Gel Dosimetry with Coumarin. Bioengineering 2018, 5 (3) , 53. https://doi.org/10.3390/bioengineering5030053
- Chaoqun SUN, Zili HUANG, Li LIU, Menglu LI, Huzhi ZHENG. Umbelliferone as a Small Molecular Peroxidase Mimic towards Sensitive Detection of H2O2 and Glucose. Analytical Sciences 2018, 34 (8) , 933-938. https://doi.org/10.2116/analsci.18P023
- Peter A. Sandwall, Henry B. Spitz, Howard R. Elson, Michael A. S. Lamba, William B. Connick, Henry Fenichel. Measuring the photon depth dose distribution produced by a medical linear accelerator in a water-equivalent radio-fluorogenic gel. Journal of Radioanalytical and Nuclear Chemistry 2016, 307 (3) , 2505-2508. https://doi.org/10.1007/s10967-015-4563-x
- Hui-Yan Wang, Xue-Cheng Liu, Zhi-Bin Huang, Da-Qing Shi. Copper-catalyzed Cyclization of 3-Acylcoumarin Hydrazone using Air as the Oxidant: Efficient Synthesis of Pyrazole-Fused Coumarin Derivatives. Journal of Heterocyclic Chemistry 2015, 52 (2) , 380-385. https://doi.org/10.1002/jhet.2052
- Luyan Meng, Yongquan Wu, Tao Yi. A ratiometric fluorescent probe for the detection of hydroxyl radicals in living cells. Chem. Commun. 2014, 50 (37) , 4843-4845. https://doi.org/10.1039/C4CC00975D
- ZhaoHui Huang, Vincent H. Crespi, James R. Chelikowsky. Electronic properties of mixed-phase graphene/ h -BN sheets using real-space pseudopotentials. Physical Review B 2013, 88 (23) https://doi.org/10.1103/PhysRevB.88.235425
- Christopher C. Perry, Sarah M. Urata, Melissa Lee, Joe A. Aguilera, Jamie R. Milligan. Radioprotective effects produced by the condensation of plasmid DNA with avidin and biotinylated gold nanoparticles. Radiation and Environmental Biophysics 2012, 51 (4) , 457-468. https://doi.org/10.1007/s00411-012-0429-6
- Miao Yu, Guo Zhang, Wenhao Wang, Jianbin Niu, Ning Zhang. Fluorescence sensing and intracellular imaging for hydroxyl radical using coumarin-modified cyclodextrin derivatives. Supramolecular Chemistry 2012, 24 (11) , 799-802. https://doi.org/10.1080/10610278.2012.717698
- Katie M. Konigsfeld, Melissa Lee, Sarah M. Urata, Joe A. Aguilera, Jamie R. Milligan. Free terminal amines in DNA-binding peptides alter the product distribution from guanine radicals produced by single electron oxidation. International Journal of Radiation Biology 2012, 88 (3) , 230-238. https://doi.org/10.3109/09553002.2012.643853
- Melissa Lee, Sarah M Urata, Joe A Aguilera, Christopher C Perry, Jamie R Milligan. Modeling the Influence of Histone Proteins on the Sensitivity of DNA to Ionizing Radiation. Radiation Research 2012, 177 (2) , 152-163. https://doi.org/10.1667/RR2812.1



