Fluorescent probes for insect ryanodine receptors: candidate anthranilic diamides.
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.
Department of Applied Chemistry, College of Science, China Agricultural University, No. 2 Yuanmingyuan West Road, Beijing 100193, China. royalwy@gmail.com.
Yi
Y
Wang
College of Agriculture and Biotechnology, China Agricultural University, No. 2 Yuanmingyuan West Road, Beijing 100193, China. guoleicau@hotmail.com.
Lei
L
Guo
Department of Applied Chemistry, College of Science, China Agricultural University, No. 2 Yuanmingyuan West Road, Beijing 100193, China. ectl@berkeley.edu.
Suzhen
S
Qi
Department of Applied Chemistry, College of Science, China Agricultural University, No. 2 Yuanmingyuan West Road, Beijing 100193, China. cauzhanghao@gmail.com.
Hao
H
Zhang
Department of Applied Chemistry, College of Science, China Agricultural University, No. 2 Yuanmingyuan West Road, Beijing 100193, China. lucklkc@163.com.
Kechang
K
Liu
Department of Applied Chemistry, College of Science, China Agricultural University, No. 2 Yuanmingyuan West Road, Beijing 100193, China. fengzilrq@163.com.
Ruiquan
R
Liu
College of Agriculture and Biotechnology, China Agricultural University, No. 2 Yuanmingyuan West Road, Beijing 100193, China. liangcau@cau.edu.cn.
Pei
P
Liang
Department of Environmental Science, Policy, and Management, University of California, Berkeley, CA 94720-3112, USA. ectl@berkeley.edu.
John E
JE
Casida
Department of Applied Chemistry, College of Science, China Agricultural University, No. 2 Yuanmingyuan West Road, Beijing 100193, China. shangzho@cau.edu.cn.
Shangzhong
S
Liu
D000818:Animals; D001578:Benzopyrans / Q000737:chemistry; D057930:Click Chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D019476:Insect Proteins / Q000737:chemistry* / Q000378:metabolism; D007306:Insecticides / Q000138:chemical synthesis* / Q000494:pharmacology; D007700:Kinetics; D007814:Larva / Q000187:drug effects / Q000254:growth & development / Q000378:metabolism; D007915:Lepidoptera / Q000187:drug effects* / Q000254:growth & development / Q000378:metabolism; D009132:Muscles / Q000187:drug effects / Q000378:metabolism; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D019837:Ryanodine Receptor Calcium Release Channel / Q000737:chemistry* / Q000378:metabolism; D062367:ortho-Aminobenzoates / Q000138:chemical synthesis* / Q000494:pharmacology
D001578:Benzopyrans; D005456:Fluorescent Dyes; D019476:Insect Proteins; D007306:Insecticides; D011720:Pyrazoles; D019837:Ryanodine Receptor Calcium Release Channel; D062367:ortho-Aminobenzoates; C517733:chlorantranilipole; C558219:cyantraniliprole