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Photoreversible stretching of a BAPTA chelator marshalling Ca²⁺-binding in aqueous media

Aurélien Ducrot, Arnaud Tron, Robin Bofinger, Ingrid Sanz Beguer, Jean-Luc Pozzo and Nathan D. McClenaghan

Beilstein J. Org. Chem. 2019, 15, 2801–2811. https://doi.org/10.3762/bjoc.15.273

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Photoreversible stretching of a BAPTA chelator marshalling Ca²⁺-binding in aqueous media

Aurélien Ducrot, Arnaud Tron, Robin Bofinger, Ingrid Sanz Beguer, Jean-Luc Pozzo and Nathan D. McClenaghan

Beilstein J. Org. Chem. 2019, 15, 2801–2811. https://doi.org/10.3762/bjoc.15.273

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Ducrot, A.; Tron, A.; Bofinger, R.; Sanz Beguer, I.; Pozzo, J.-L.; McClenaghan, N. D. Beilstein J. Org. Chem. 2019, 15, 2801–2811. doi:10.3762/bjoc.15.273

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TY  - JOUR
A1  - Ducrot, Aurélien
A1  - Tron, Arnaud
A1  - Bofinger, Robin
A1  - Sanz Beguer, Ingrid
A1  - Pozzo, Jean-Luc
A1  - McClenaghan, Nathan D.
T1  - Photoreversible stretching of a BAPTA chelator marshalling Ca2+-binding in aqueous media
JF  - Beilstein Journal of Organic Chemistry
PY  - 2019///
VL  - 15
SP  - 2801
EP  - 2811
SN  - 1860-5397
DO  - 10.3762/bjoc.15.273
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.15.273
KW  - azobenzene
KW  - BAPTA
KW  - calcium binding
KW  - photorelease
KW  - photoswitch
N2  - Free calcium ion concentration is known to govern numerous biological processes and indeed calcium acts as an important biological secondary messenger for muscle contraction, neurotransmitter release, ion-channel gating, and exocytosis. As such, the development of molecules with the ability to instantaneously increase or diminish free calcium concentrations potentially allows greater control over certain biological functions. In order to permit remote regulation of Ca2+, a selective BAPTA-type synthetic receptor / host was integrated with a photoswitchable azobenzene motif, which upon photoirradiation would enhance (or diminish) the capacity to bind calcium upon acting on the conformation of the adjacent binding site, rendering it a stronger or weaker binder. Photoswitching was studied in pseudo-physiological conditions (pH 7.2, [KCl] = 100 mM) and dissociation constants for azobenzene cis- and trans-isomers have been determined (0.230 μM and 0.102 μM, respectively). Reversible photoliberation/uptake leading to a variation of free calcium concentration in solution was detected using a fluorescent Ca2+ chemosensor.
ER  -

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Scholarly Works

Egodawaththa, N. M.; Rajhel, O.; Ma, J.; Guruge, C.; Pabarue, A. B.; Harris, E.; Peverati, R.; Nesnas, N. Highly efficient Ca2+ chelation activated by visible light. Organic & biomolecular chemistry 2024, 22, 7194–7202. doi:10.1039/d4ob00951g
Chen, H.; Tang, Z.; Yang, Y.; Hao, Y.; Chen, W. Recent Advances in Photoswitchable Fluorescent and Colorimetric Probes. Molecules (Basel, Switzerland) 2024, 29, 2521. doi:10.3390/molecules29112521
Ludwig, C.; Xie, J. The Growing Field of Photoswitchable Macrocycles: A Promising Way to Tune Various Properties with Light. ChemPhotoChem 2023, 7. doi:10.1002/cptc.202300126
Chen-Wu, J.; Máximo, P.; Remón, P.; Parola, A. J.; Basílio, N.; Pischel, U. Phototransduction in a supramolecular cascade: a mimic for essential features of the vision process. Chemical communications (Cambridge, England) 2023, 59, 3431–3434. doi:10.1039/d3cc00384a
Yang, Z.; Liu, Z.; Yuan, L. Recent Advances of Photoresponsive Supramolecular Switches. Asian Journal of Organic Chemistry 2020, 10, 74–90. doi:10.1002/ajoc.202000501

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aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)