The DOI matches its Crossref record; 30 of the 30 references it cites were found in a registry or an index.
Tunable Heptamethine–Azo Dye Conjugate as an NIR Fluorescent Probe for the Selective Detection of Mitochondrial Glutathione over Cysteine and Homocysteine
Abstract
Although a lot of mitochondria-targeting biothiol probes have been developed and applied to cellular imaging through thiol-induced disulfide cleavage or Michael addition reactions, relatively few probes assess mitochondrial GSH with high selectivity over Cys and Hcy and with NIR fluorescence capable of noninvasive imaging in biological samples. In order to monitor mitochondrial GSH with low background autofluorescence, we designed a heptamethine-azo conjugate as an NIR fluorescent probe by introducing a tunable lipophilic cation unit as the biomarker for mitochondria and a nitroazo group as the GSH-selective reaction site as well as the fluorescence quencher. The probe exhibited a dramatic off-on NIR fluorescence response toward GSH with high selectivity over other amino acids including Cys and Hcy. Further application to cellular imaging indicated that the probe was highly responsive to the changes of mitochondrial GSH in cells.
Overview
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Verification
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Citations
Cites
Recent progress in the development of near-infrared fluorescent probes for bioimaging applications
Guo, Z., Park, S., Yoon, J., & Shin, I. (2014) · Chem. Soc. Rev. · doi:10.1039/c3cs60271k · Cited by 1,801
Niu, L.-Y., Guan, Y.-S., Chen, Y.-Z., Wu, L.-Z., Tung, C.-H., & Yang, Q.-Z. (2012) · Journal of the American Chemical Society · doi:10.1021/ja309079f · Cited by 901
Disulfide-Cleavage-Triggered Chemosensors and Their Biological Applications
Lee, M. H., Yang, Z., Lim, C. W., Lee, Y. H., Dongbang, S., Kang, C., & Kim, J. S. (2013) · Chemical Reviews · doi:10.1021/cr300358b · Cited by 821
Yang, X., Guo, Y., & Strongin, R. M. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201103759 · Cited by 658
Neuroprotection by the Metabolic Antioxidant α-Lipoic Acid
Packer, L., Tritschler, H. J., & Wessel, K. (1997) · Free Radical Biology and Medicine · doi:10.1016/s0891-5849(96)00269-9 · Cited by 639
Guo, Z., Nam, S., Park, S., & Yoon, J. (2012) · Chemical Science · doi:10.1039/c2sc20540h · Cited by 431
Ratiometric Detection of Mitochondrial Thiols with a Two-Photon Fluorescent Probe
Lim, C. S., Masanta, G., Kim, H. J., Han, J. H., Kim, H. M., & Cho, B. R. (2011) · Journal of the American Chemical Society · doi:10.1021/ja205081s · Cited by 365
Self-citationSpectroscopic Properties of Organic Azo Compounds
Rau, H. (1973) · Angewandte Chemie International Edition in English · doi:10.1002/anie.197302241 · Cited by 336
Ogawa, M., Kosaka, N., Choyke, P. L., & Kobayashi, H. (2009) · Cancer Research · doi:10.1158/0008-5472.can-08-3116 · Cited by 326
A fluorescein-based probe with high selectivity to cysteine over homocysteine and glutathione
Wang, H., Zhou, G., Gai, H., & Chen, X. (2012) · Chemical Communications · doi:10.1039/c2cc33932c · Cited by 271
Selective Phosphorescence Chemosensor for Homocysteine Based on an Iridium(III) Complex
Chen, H., Zhao, Q., Wu, Y., Li, F., Yang, H., Yi, T., & Huang, C. (2007) · Inorganic Chemistry · doi:10.1021/ic7010887 · Cited by 269
Shao, N., Jin, J., Wang, H., Zheng, J., Yang, R., Chan, W., & Abliz, Z. (2010) · Journal of the American Chemical Society · doi:10.1021/ja908215t · Cited by 268
Wang, R., Yu, F., Chen, L., Chen, H., Wang, L., & Zhang, W. (2012) · Chemical Communications · doi:10.1039/c2cc36088h · Cited by 262
Fluorescence turn-on probe for homocysteine and cysteine in water
Lee, K.-S., Kim, T.-K., Lee, J. H., Kim, H.-J., & Hong, J.-I. (2008) · Chemical Communications · doi:10.1039/b814581d · Cited by 238
Self-citationFolate-Based Near-Infrared Fluorescent Theranostic Gemcitabine Delivery
Yang, Z., Lee, J. H., Jeon, H. M., Han, J. H., Park, N., He, Y., Lee, H., Hong, K. S., Kang, C., & Kim, J. S. (2013) · Journal of the American Chemical Society · doi:10.1021/ja405372k · Cited by 212
Self-citationA NIR heptamethine dye with intrinsic cancer targeting, imaging and photosensitizing properties
Tan, X., Luo, S., Wang, D., Su, Y., Cheng, T., & Shi, C. (2012) · Biomaterials · doi:10.1016/j.biomaterials.2011.11.081 · Cited by 210
Packer, L. (1998) · Drug Metabolism Reviews · doi:10.3109/03602539808996311 · Cited by 207
Wahlländer, A., Soboll, S., Sies, H., Ingrid, L., & Monika, M. (1979) · FEBS Letters · doi:10.1016/0014-5793(79)80069-1 · Cited by 189
Intense Fluorescence from Light-Driven Self-Assembled Aggregates of Nonionic Azobenzene Derivative
Han, M., & Hara, M. (2005) · Journal of the American Chemical Society · doi:10.1021/ja0509275 · Cited by 187
Narayanan, N., & Patonay, G. (1995) · The Journal of Organic Chemistry · doi:10.1021/jo00113a018 · Cited by 181
Strekowski, L., Lipowska, M., & Patonay, G. (1992) · The Journal of Organic Chemistry · doi:10.1021/jo00043a009 · Cited by 180
Mitochondrial Thioredoxin-Responding Off–On Fluorescent Probe
Lee, M. H., Han, J. H., Lee, J.-H., Choi, H. G., Kang, C., & Kim, J. S. (2012) · Journal of the American Chemical Society · doi:10.1021/ja308446y · Cited by 161
Kiyose, K., Aizawa, S., Sasaki, E., Kojima, H., Hanaoka, K., Terai, T., Urano, Y., & Nagano, T. (2009) · Chemistry - A European Journal · doi:10.1002/chem.200900035 · Cited by 138
Synthesis and Evaluation of Polyhydroxylated Near-Infrared Carbocyanine Molecular Probes
Zhang, Z., & Achilefu, S. A. (2004) · Organic Letters · doi:10.1021/ol049258a · Cited by 123
Critical Role of Mitochondrial Glutathione in the Survival of Hepatocytes during Hypoxia
Lluis, J. M., Morales, A., Blasco, C., Colell, A., Marí, M., García‐Ruiz, C., & Fernández-Checa, J. C. (2004) · Journal of Biological Chemistry · doi:10.1074/jbc.m408244200 · Cited by 107
Some properties of mitochondrial glutathione
Jocelyn, P. C. (1975) · Biochimica et Biophysica Acta (BBA) - Bioenergetics · doi:10.1016/0005-2728(75)90148-6 · Cited by 86
Shan, X., Jones, D. P., Hashmi, M., & Anders, M. W. (1993) · Chemical Research in Toxicology · doi:10.1021/tx00031a012 · Cited by 86
A Fast Response Highly Selective Probe for the Detection of Glutathione in Human Blood Plasma
Guo, Y., Yang, X., Hakuna, L., Barve, A., Escobedo, J. O., Lowry, M., & Strongin, R. M. (2012) · Sensors · doi:10.3390/s120505940 · Cited by 84
Zhang, C., Spokoyny, A. M., Zou, Y., Simon, M. D., & Pentelute, B. L. (2013) · Angewandte Chemie International Edition · doi:10.1002/anie.201306430 · Cited by 61
Fluorescence spectroscopic analysis of indocyanine green J aggregates in water
Rotermund, F., Weigand, R., Holzer, W., Wittmann, M., & Penzkofer, А. (1997) · Journal of Photochemistry and Photobiology A Chemistry · doi:10.1016/s1010-6030(97)00167-6 · Cited by 30
Cited by
Recent Strategies to Develop Innovative Photosensitizers for Enhanced Photodynamic Therapy
Pham, T. C., Nguyen, V.-N., Choi, Y., Lee, S., & Yoon, J. (2021) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00381 · Cited by 1,813
Design strategies of fluorescent probes for selective detection among biothiols
Niu, L.-Y., Chen, Y.-Z., Zheng, H.-R., Wu, L.-Z., Tung, C.-H., & Yang, Q.-Z. (2015) · Chemical Society Reviews · doi:10.1039/c5cs00152h · Cited by 870
Umezawa, K., Yoshida, M., Kamiya, M., Yamasoba, T., & Urano, Y. (2017) · Nature Chemistry · doi:10.1038/nchem.2648 · Cited by 508
Near-infrared (NIR) fluorescence-emitting small organic molecules for cancer imaging and therapy
Li, H., Kim, Y., Jung, H., Hyun, J. Y., & Shin, I. (2022) · Chemical Society Reviews · doi:10.1039/d2cs00722c · Cited by 356
Mitochondria‐Targeted Small‐Molecule Fluorophores for Dual Modal Cancer Phototherapy
Luo, S., Tan, X., Fang, S., Wang, Y., Liu, T., Wang, X., Yuan, Y., Sun, H., Qi, Q., & Shi, C. (2016) · Advanced Functional Materials · doi:10.1002/adfm.201600159 · Cited by 285
Metadata
- Authors
- Lim, S.-Y., Hong, K.-H., Kim, D. I., Kwon, H., & Kim, H.-J.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2014-05-01
- Volume
- 136
- Issue
- 19
- Pages
- 7018-7025
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2024237542
- Cited by
- 461
- References
- 30
- FWCI
- 23.70
- Type
- journal article
- Language
- en
- Open access
- closed
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
Data sources
Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
