Tuning Directed Photooxidation-Induced Conversion of Pyrrole-Based Styryl Coumarin Dual-Color Photoconverters.
fluorescent probes
molecular tuning
photoconversion
photooxidation
photoswitching
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
06 Apr 2023
06 Apr 2023
Historique:
received:
15
12
2022
medline:
1
2
2023
pubmed:
1
2
2023
entrez:
31
1
2023
Statut:
ppublish
Résumé
Dual-emissive photoconvertible fluorophores (DPCFs) are powerful tools to unambiguously track labeled cells in bioimaging. We recently introduced a new rational mechanism called directed photooxidation-induced conversion (DPIC) enabling efficient DPCFs to be obtained by conjugating a coumarin to aromatic singlet-oxygen reactive moieties (ASORMs). Pyrrole was found to be a suitable ASORM as it provided a high hypsochromic shift along with a fast and efficient conversion. By synthesizing various pyrrole-based styryl coumarin dyes, we showed that the photoconversion properties, including the quantum yield of photoconversion and the chemical yield of conversion can be tuned by chemical modification of the pyrrole. These modifications led to an improved dual emissive converter, SCP-Boc, which displayed a high brightness and an enhanced photoconversion yield of 63 %. SCP-Boc was successfully used to sequentially photoconvert cells by laser scanning confocal microscopy.
Identifiants
pubmed: 36719328
doi: 10.1002/chem.202203933
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202203933Subventions
Organisme : Agence Nationale de la Recherche
ID : 19-CE29-0005-01
Informations de copyright
© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
Références
V. Adam, R. Berardozzi, M. Byrdin, D. Bourgeois, Curr. Opin. Chem. Biol. 2014, 20, 92-102.
Y. Zhang, S. Tang, E. R. Thapaliya, L. Sansalone, F. M. Raymo, Chem. Commun. 2018, 54, 8799-8809.
I. Yildiz, E. Deniz, F. M. Raymo, Chem. Soc. Rev. 2009, 38, 1859-1867.
Y. Zhang, Y. Zheng, Y. Meana, F. M. Raymo, Chem. Eur. J. 2021, 27, 11257-11267.
X. Zhang, D. Guan, Y. Liu, J. Liu, K. Sun, S. Chen, Y. Zhang, B. Zhao, T. Zhai, Y. Zhang, F. Li, Q. Liu, Angew. Chem. Int. Ed. 2022, 61, e202211767.
D. Maurel, S. Banala, T. Laroche, K. Johnsson, ACS Chem. Biol. 2010, 5, 507-516.
Y. Cho, H. J. An, T. Kim, C. Lee, N. K. Lee, J. Am. Chem. Soc. 2021, 143, 14125-14135.
H. Fukushima, S. S. Matikonda, S. M. Usama, A. Furusawa, T. Kato, L. Štacková, P. Klán, H. Kobayashi, M. J. Schnermann, J. Am. Chem. Soc. 2022, 144 (25), 11075-11080.
S. Tang, Y. Zhang, P. Dhakal, L. Ravelo, C. L. Anderson, K. M. Collins, F. M. Raymo, J. Am. Chem. Soc. 2018, 140, 4485-4488.
N. Lorén, J. Hagman, J. K. Jonasson, H. Deschout, D. Bernin, F. Cella-Zanacchi, A. Diaspro, J. G. McNally, M. Ameloot, N. Smisdom, M. Nydén, A.-M. Hermansson, M. Rudemo, K. Braeckmans, Q. Rev. Biophys. 2015, 48, 323-387.
“Intracellular Macromolecular Mobility Measured by Fluorescence Recovery after Photobleaching with Confocal Laser Scanning Microscopes | Molecular Biology of the Cell,” can be found under https://www.molbiolcell.org/doi/10.1091/mbc.e04-06-0496.
D. Pan, Z. Hu, F. Qiu, Z.-L. Huang, Y. Ma, Y. Wang, L. Qin, Z. Zhang, S. Zeng, Y.-H. Zhang, Nat. Commun. 2014, 5, 5573.
C. S. Wijesooriya, J. A. Peterson, P. Shrestha, E. J. Gehrmann, A. H. Winter, E. A. Smith, Angew. Chem. Int. Ed. 2018, 57, 12685-12689;
Angew. Chem. 2018, 130, 12867-12871.
Y. Zhang, K.-H. Song, S. Tang, L. Ravelo, J. Cusido, C. Sun, H. F. Zhang, F. M. Raymo, J. Am. Chem. Soc. 2018, 140, 12741-12745.
J. A. Peterson, C. Wijesooriya, E. J. Gehrmann, K. M. Mahoney, P. P. Goswami, T. R. Albright, A. Syed, A. S. Dutton, E. A. Smith, A. H. Winter, J. Am. Chem. Soc. 2018, 140, 7343-7346.
P. Shrestha, K. C. Dissanayake, E. J. Gehrmann, C. S. Wijesooriya, A. Mukhopadhyay, E. A. Smith, A. H. Winter, J. Am. Chem. Soc. 2020, 142 (36), 15505-15512.
J. Tang, M. A. Robichaux, K.-L. Wu, J. Pei, N. T. Nguyen, Y. Zhou, T. G. Wensel, H. Xiao, J. Am. Chem. Soc. 2019, 141, 14699-14706.
L. Wang, S. Wang, J. Tang, V. B. Espinoza, A. Loredo, Z. Tian, R. B. Weisman, H. Xiao, Chem. Sci. 2021, 12, 15572-15580.
R. Ando, H. Hama, M. Yamamoto-Hino, H. Mizuno, A. Miyawaki, Proc. Nat. Acad. Sci. 2002, 99, 12651-12656.
V. Adam, B. Moeyaert, C. C. David, H. Mizuno, M. Lelimousin, P. Dedecker, R. Ando, A. Miyawaki, J. Michiels, Y. Engelborghs, J. Hofkens, Chem. Biol. 2011, 18, 1241-1251.
S. A. McKinney, C. S. Murphy, K. L. Hazelwood, M. W. Davidson, L. L. Looger, Nat. Methods 2009, 6, 131-133.
B. Moeyaert, N. Nguyen Bich, E. De Zitter, S. Rocha, K. Clays, H. Mizuno, L. van Meervelt, J. Hofkens, P. Dedecker, ACS Nano 2014, 8, 1664-1673.
N. G. Gurskaya, V. V. Verkhusha, A. S. Shcheglov, D. B. Staroverov, T. V. Chepurnykh, A. F. Fradkov, S. Lukyanov, K. A. Lukyanov, Nat. Biotechnol. 2006, 24, 461-465.
K. Nienhaus, G. U. Nienhaus, RSC Chem. Biol. 2021, 2, 796-814.
R. M. Wachter, Int. J. Mol. Sci. 2017, 18, 1792.
J. B. Grimm, L. D. Lavis, Nat. Methods 2022, 19, 149-158.
L. Dirix, K. Kennes, E. Fron, Z. Debyser, M. van der Auweraer, J. Hofkens, S. Rocha, ChemPhotoChem 2018, 2, 433-441.
S. J. J. Kwok, M. Choi, B. Bhayana, X. Zhang, C. Ran, S.-H. Yun, Sci. Rep. 2016, 6, 23866.
M. N. Tran, D. M. Chenoweth, Angew. Chem. Int. Ed. 2015, 54, 6442-6446;
Angew. Chem. 2015, 127, 6542-6546.
M. N. Tran, R.-A. F. Rarig, D. M. Chenoweth, Chem. Sci. 2015, 6, 4508-4512.
J. V. Jun, C. M. Haney, R. J. Karpowicz, S. Giannakoulias, V. M.-Y. Lee, E. J. Petersson, D. M. Chenoweth, J. Am. Chem. Soc. 2019, 141, 1893-1897.
X. Ling, L. Huang, Y. Li, Q. Wan, Z. Wang, A. Qin, M. Gao, B. Z. Tang, Mater. Horiz. 2020, 7, 2696-2701.
P. Wei, J.-X. Zhang, Z. Zhao, Y. Chen, X. He, M. Chen, J. Gong, H. H.-Y. Sung, I. D. Williams, J. W. Y. Lam, B. Z. Tang, J. Am. Chem. Soc. 2018, 140, 1966-1975.
Q. Gong, X. Zhang, W. Li, X. Guo, Q. Wu, C. Yu, L. Jiao, Y. Xiao, E. Hao, J. Am. Chem. Soc. 2022, 144 (48), 21992-21999.
A. L. Carlson, J. Fujisaki, J. Wu, J. M. Runnels, R. Turcotte, C. L. Celso, D. T. Scadden, T. B. Strom, C. P. Lin, PLoS One 2013, 8, e69257.
S. S. Matikonda, D. A. Helmerich, M. Meub, G. Beliu, P. Kollmannsberger, A. Greer, M. Sauer, M. J. Schnermann, ACS Cent. Sci. 2021, 7, 1144-1155.
A. N. Butkevich, M. L. Bossi, G. Lukinavičius, S. W. Hell, J. Am. Chem. Soc. 2019, 141, 981-989.
L. Saladin, V. Breton, O. Dal Pra, A. S. Klymchenko, L. Danglot, P. Didier, M. Collot, Angew. Chem. Int. Ed. 2023, 62, e202215085.
D. A. Lightner, G. S. Bisacchi, R. D. Norris, J. Am. Chem. Soc. 1976, 98, 802-807.
J. K. Howard, K. J. Rihak, A. C. Bissember, J. A. Smith, Chem. Asian J. 2016, 11, 155-167.
D. A. Lightner, Photochem. Photobiol. 1977, 26, 427-436.
R. Heim, A. B. Cubitt, R. Y. Tsien, Nature 1995, 373, 663-664.
N. Zeinali, I. Oluwoye, M. Altarawneh, B. Z. Dlugogorski, Theor. Chem. Acc. 2019, 138, 90.
M. A. Thompson, J. S. Biteen, S. J. Lord, N. R. Conley, W. E. Moerner, Molecules and Methods for Super-Resolution Imaging, Methods in Enzymology, Volume 475, Nils G. Walter, Editor (Elsevier, New York, 2010), Chapter 2, pp. 27-59.9.