ACS Publications. Most Trusted. Most Cited. Most Read
Phosphorescent Sensor for Phosphorylated Peptides Based on an Iridium Complex

OR SEARCH CITATIONS

My Activity
Publications

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Org. Chem. 2014, 79, 13, 6000-6005
    Article

    Phosphorescent Sensor for Phosphorylated Peptides Based on an Iridium Complex
    Click to copy article linkArticle link copied!

    View Author Information
    † Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-747, South Korea
    ‡ Department of Chemistry, School of Natural Science, Ulsan National Institute of Science and Technology, Ulsan 689-798, South Korea
    *E-mail: [email protected]
    *E-mail: [email protected]
    Other Access OptionsSupporting Information (1)

    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2014, 79, 13, 6000–6005
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo5005263
    Published June 12, 2014
    Copyright © 2014 American Chemical Society
    Request reuse permissions

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    A bis[(4,6-difluorophenyl)pyridinato-N,C2′]iridium(III) picolinate (FIrpic) derivative coupled with bis(Zn2+–dipicolylamine) (ZnDPA) was developed as a sensor (1) for phosphorylated peptides, which are related to many cellular mechanisms. As a control, a fluorescent sensor (2) based on anthracene coupled to ZnDPA was also prepared. When the total negative charge on the phosphorylated peptides was changed to −2, −4, and −6, the emission intensity of sensor 1 gradually increased by factors of up to 7, 11, and 16, respectively. In contrast, there was little change in the emission intensity of sensor 1 upon the addition of a neutral phosphorylated peptide, non-phosphorylated peptides, or various anions such as CO32–, NO3–, SO42–, phosphate, azide, and pyrophosphate. Furthermore, sensor 1 could be used to visually discriminate between phosphorylated peptides and adenosine triphosphate in aqueous solution under a UV–vis lamp, unlike fluorescent sensor 2. This enhanced luminance of phosphorescent sensor 1 upon binding to a phosphorylated peptide is attributed to a reduction in the repulsion between the Zn2+ ions due to the phenoxy anion, its strong metal-to-ligand charge transfer character, and a reduction in self-quenching.

    Copyright © 2014 American Chemical Society

    Subjects

    what are subjects

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    Job’s plots between sensors (1 and 2) and p-Tyr, UV and PL spectra of sensors 1 and 2, and titration PL spectrum of sensor 1 with various peptides (II–VI) and ATP. This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!

    This article is cited by 21 publications.

    1. Guo Zou, Li Zhao, Longwei Zeng, Kaijun Luo, Hailiang Ni, Haifeng Wang, Quan Li, Wenhao Yu, Xuelian Li. Columnar Iridium(III) Metallomesogens Based on Polycatenar Pyridyltetrazolate with Ambipolar Carrier Mobility Behavior. Inorganic Chemistry 2019, 58 (1) , 861-869. https://doi.org/10.1021/acs.inorgchem.8b02984
    2. Juan Sanz-Villafruela, Cristina Bermejo-Casadesús, Marta Martínez-Alonso, Artur Moro, João C. Lima, Anna Massaguer, Gustavo Espino. Towards efficient Ir( iii ) anticancer photodynamic therapy agents by extending π-conjugation on N^N ligands. Dalton Transactions 2024, 53 (27) , 11393-11409. https://doi.org/10.1039/D4DT00390J
    3. Byung Hak Jhun, Dayoon Song, Soo Young Park, Youngmin You. Phosphorescent Ir(III) Complexes for Biolabeling and Biosensing. Topics in Current Chemistry 2022, 380 (5) https://doi.org/10.1007/s41061-022-00389-3
    4. Ruixi Xu, Yuting Wu, Zhe Liu, Jinfeng Liu, Xicheng Liu. Lysosomal Targeted Cyclometallic Iridium(Ⅲ) Salicylaldehyde-Coumarin Schiff Base Complexes and Anticancer Application. Frontiers in Chemistry 2022, 10 https://doi.org/10.3389/fchem.2022.906954
    5. Shuai Wang, Lichong Gong, Georges El Fakhri, Junfeng Wang. Efficient synthesis of 6,6′-diamido-2,2′-dipicolylamine ligands for potential phosphate anion sensing. New Journal of Chemistry 2021, 45 (36) , 16833-16840. https://doi.org/10.1039/D1NJ03030B
    6. Pedro Mateus, Rita Delgado. Zinc( ii ) and copper( ii ) complexes as tools to monitor/inhibit protein phosphorylation events. Dalton Transactions 2020, 49 (47) , 17076-17092. https://doi.org/10.1039/D0DT03503C
    7. Sushil K. Dwivedi, Rashid Ali, Manjeet Singh, Tulika Gupta, Aditya K. Kar, Ved Prakash, Anbumani Sadasivam, Satyakam Patnaik, Arvind Misra. A simple naphthalimide based PET probe for Fe3+ and selective detection of pyrophosphate through displacement approach: Cell imaging studies and logic interpretation. Journal of Photochemistry and Photobiology A: Chemistry 2020, 403 , 112854. https://doi.org/10.1016/j.jphotochem.2020.112854
    8. Ku Sun Choung, Karen Marroquin, Thomas S. Teets. Cyclometalated iridium–BODIPY ratiometric O 2 sensors. Chemical Science 2019, 10 (19) , 5124-5132. https://doi.org/10.1039/C9SC00696F
    9. Pushap Raj, Amanpreet Singh, Ajnesh Singh, Ashutosh Singh, Neha Garg, Navneet Kaur, Narinder Singh. Pyrophosphate Prompted Aggregation‐Induced Emission: Chemosensor Studies, Cell Imaging, Cytotoxicity, and Hydrolysis of the Phosphoester Bond with Alkaline Phosphatase. European Journal of Inorganic Chemistry 2019, 2019 (5) , 628-638. https://doi.org/10.1002/ejic.201801173
    10. Marta Martínez‐Alonso, Natalia Busto, Larry Danilo Aguirre, Leticia Berlanga, M. Carmen Carrión, José V. Cuevas, Ana M. Rodríguez, Arancha Carbayo, Blanca R. Manzano, Enrique Ortí, Félix A. Jalón, Begoña García, Gustavo Espino. Strong Influence of the Ancillary Ligand over the Photodynamic Anticancer Properties of Neutral Biscyclometalated Ir III Complexes Bearing 2‐Benzoazole‐Phenolates. Chemistry – A European Journal 2018, 24 (66) , 17523-17537. https://doi.org/10.1002/chem.201803784
    11. Massimiliano Francesco Peana, Serenella Medici, Maria Antonietta Zoroddu. The Intriguing Potential of “Minor” Noble Metals: Emerging Trends and New Applications. 2018, 49-72. https://doi.org/10.1007/978-3-319-74814-6_2
    12. Dik‐Lung Ma, Chun Wu, Guodong Li, Chung‐Hang Leung. Group 8–9 Metal-Based Luminescent Chemosensors for Protein Biomarker Detection. Journal of Analysis and Testing 2018, 2 (1) , 77-89. https://doi.org/10.1007/s41664-017-0045-1
    13. Se Won Bae, Jae Il Kim, Inseong Choi, Jiha Sung, Jong-In Hong, Woon-Seok Yeo. Zinc Ion-immobilized Magnetic Microspheres for Enrichment and Identification of Multi-phosphorylated Peptides by Mass Spectrometry. Analytical Sciences 2017, 33 (12) , 1381-1385. https://doi.org/10.2116/analsci.33.1381
    14. Teresa Ramón‐Márquez, Marta Marín‐Suárez, Alberto Fernández‐Gutiérrez, J. F. Fernández‐Sánchez. Iridium Complexes in the Development of Optical Sensors. 2017, 479-539. https://doi.org/10.1002/9781119007166.ch10
    15. P.T. Gunning, D. Kraskouskaya, J.S. Park, A.D. Cabral, R.F. Gomez-Biagi. Fluorescence-Based Chemosensors for the Detection of Biologically Relevant Phosphates in Water. 2017, 113-160. https://doi.org/10.1016/B978-0-12-409547-2.12554-5
    16. Lígia M. Mesquita, Pedro Mateus, Rui D. V. Fernandes, Olga Iranzo, Vânia André, Filipe Tiago de Oliveira, Carlos Platas-Iglesias, Rita Delgado. Recognition of phosphopeptides by a dinuclear copper( ii ) macrocyclic complex in a water : methanol 50 : 50 v/v solution. Dalton Transactions 2017, 46 (29) , 9549-9564. https://doi.org/10.1039/C7DT01724C
    17. Dik-Lung Ma, Modi Wang, Chenfu Liu, Xiangmin Miao, Tian-Shu Kang, Chung-Hang Leung. Metal complexes for the detection of disease-related protein biomarkers. Coordination Chemistry Reviews 2016, 324 , 90-105. https://doi.org/10.1016/j.ccr.2016.07.010
    18. Sarah H. Hewitt, Andrew J. Wilson. Metal complexes as “protein surface mimetics”. Chemical Communications 2016, 52 (63) , 9745-9756. https://doi.org/10.1039/C6CC03457H
    19. M. Becuwe, P.-E. Danjou, F. Cazier, P. Woisel, F. Delattre. Immobilization of fluorescent chemosensor on pyrogenic silica: A promising device for gaseous detection. Journal of Colloid and Interface Science 2015, 450 , 62-67. https://doi.org/10.1016/j.jcis.2015.02.041
    20. Judith P. Morales-Cerón, Verónica Salazar-Pereda, Daniel Mendoza-Espinosa, José G. Alvarado-Rodríguez, Julián Cruz-Borbolla, Noemí Andrade-López, José M. Vásquez-Pérez. Synthesis of Ir( iii ) complexes with Tp Me2 and acac ligands and their reactivity with electrophiles. Dalton Transactions 2015, 44 (31) , 13881-13889. https://doi.org/10.1039/C5DT01937K
    21. Aihui Liang, Lei Ying, Fei Huang. Recent Progresses of Iridium Complex-Containing Macromolecules for Solution-Processed Organic Light-Emitting Diodes. Journal of Inorganic and Organometallic Polymers and Materials 2014, 24 (6) , 905-926. https://doi.org/10.1007/s10904-014-0099-8
    Download PDF
    Go to The Journal of Organic Chemistry
    Get e-Alerts
    Get e-Alerts

    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2014, 79, 13, 6000–6005
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo5005263
    Published June 12, 2014
    Copyright © 2014 American Chemical Society
    Request reuse permissions

    Article Views

    1650

    Altmetric

    -

    Citations

    21
    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.