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Molecules 2014, 19(4), 4105-4114; doi:10.3390/molecules19044105
Article

Fluorescent Probes for Insect Ryanodine Receptors: Candidate Anthranilic Diamides

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1 Department of Applied Chemistry, College of Science, China Agricultural University, No. 2 Yuanmingyuan West Road, Beijing 100193, China 2 College of Agriculture and Biotechnology, China Agricultural University, No. 2 Yuanmingyuan West Road, Beijing 100193, China 3 Department of Environmental Science, Policy, and Management, University of California, Berkeley, CA 94720-3112, USA
* Author to whom correspondence should be addressed.
Received: 16 January 2014 / Revised: 13 March 2014 / Accepted: 21 March 2014 / Published: 2 April 2014
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Abstract

Diamide insecticides with high efficacy against pests and good environmental safety are broadly applied in crop protection. They act at a poorly-defined site in the very complex ryanodine (Ry) receptor (RyR) potentially accessible to a fluorescent probe. Two N-propynyl analogs of the major anthranilic diamide insecticides chlorantraniliprole (Chlo) and cyantraniliprole (Cyan) were accordingly synthesized and converted into two fluorescent ligands by click reaction coupling with 3-azido-7-hydroxy-2H-chromen-2-one. The new diamide analogs and fluorescent ligands were shown to be nearly as potent as Chlo and Cyan in inhibition of [3H]Chlo binding and stimulation of [3H]Ry binding in house fly thoracic muscle RyR. Although the newly synthesized compounds had only moderate activity in insect larvicidal activity assays, their high in vitro potency in a validated insect RyR binding assay encourages further development of fluorescent probes for insect RyRs.
Keywords: fluorescent probe; affinity; ryanodine receptor fluorescent probe; affinity; ryanodine receptor
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Wang, Y.; Guo, L.; Qi, S.; Zhang, H.; Liu, K.; Liu, R.; Liang, P.; Casida, J.E.; Liu, S. Fluorescent Probes for Insect Ryanodine Receptors: Candidate Anthranilic Diamides. Molecules 2014, 19, 4105-4114.

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