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| Azopyridine-imidacloprid derivatives as photoresponsive neonicotinoids |
| Shen Lia, Run-Jiang Songa, Dong-Hui Wangb, Xue Tiana, Xu-Sheng Shaoa, Zhong Lia |
a Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China;
b College of Life Science, Perking University, Beijing 100871, China |
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Abstract A series of imidacloprid derivatives containing an azopyridine motif as a photoswitchable functional group were designed and synthesized. The new version of photoresponsive imidacloprid analogues showed improved solubility in comparison with their azobenzene analogues. 1.2 to 2-fold activity difference was observed for these azopyridine-imidacloprids against house fly (Musca domestica) and cowpea aphid (Aphis craccivora) upon irradiation.
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Received: 24 February 2016
Published: 31 March 2016
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| Fund:This work was financial supported by National Natural Science Foundation of China (Nos. 21372079, 21472046), Shanghai Pujiang Program (No. 14PJD012) and the Fundamental Research Funds for the Central Universities (No. 222201414015). |
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Corresponding Authors:
Xu-Sheng Shao
E-mail: shaoxusheng@ecust.edu.cn
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| [1] |
P. Gorostiza, E. Isacoff, Optical switches and triggers for the manipulation of ion channels and pores, Mol. Biosyst. 3(2007) 686-704.
|
| [2] |
F. Hamon, F. Djedaini-Pilard, F. Barbot, C. Len, Azobenzenes-synthesis and carbohydrate applications, Tetrahedron 65(2009) 10105-10123.
|
| [3] |
C.W. Riggsbee, A. Deiters, Recent advances in the photochemical control of protein function, Trends Biotechnol. 28(2010) 468-475.
|
| [4] |
T. Fehrentz, M. Schonberger, D. Trauner, Optochemical genetics, Angew. Chem. Int. Ed. 50(2011) 12156-12182.
|
| [5] |
W. Szymanski, J.M. Beierle, H.A. Kistemaker, W.A. Velema, B.L. Feringa, Reversible photocontrol of biological systems by the incorporation of molecular photoswitches, Chem. Rev. 113(2013) 6114-6178.
|
| [6] |
M. Banghart, K. Borges, E. Isacoff, D. Trauner, R.H. Kramer, Light-activated ion channels for remote control of neuronal firing, Nat. Neurosci. 7(2004) 1381-1386.
|
| [7] |
S. Samanta, A.A. Beharry, O. Sadovski, et al., Photoswitching azo compounds in vivo with red light, J. Am. Chem. Soc. 135(2013) 9777-9784.
|
| [8] |
W.A. Velema, W. Szymanski, B.L. Feringa, Photopharmacology:beyond proof of principle, J. Am. Chem. Soc. 136(2014) 2178-2191.
|
| [9] |
J. Broichhagen, J.A. Frank, D. Trauner, A roadmap to success in photopharmacology, Acc. Chem. Res. 48(2015) 1947-1960.
|
| [10] |
W.A. Velema, J.P. van der Berg, M.J. Hansen, et al., Optical control of antibacterial activity, Nat. Chem. 5(2013) 924-928.
|
| [11] |
L. Yue, M. Pawlowski, S.S. Dellal, et al., Robust photoregulation of GABAA receptors by allosteric modulation with a propofol analogue, Nat. Commun. 3(2012) 1095.
|
| [12] |
M. Stein, S.J. Middendorp, V. Carta, et al., Azo-propofols:photochromic potentiators of GABA (A) receptors, Angew. Chem. Int. Ed. 51(2012) 10500-10504.
|
| [13] |
J. Broichhagen, M. Schonberger, S.C. Cork, et al., Optical control of insulin release using a photoswitchable sulfonylurea, Nat. Commun. 5(2014) 5116.
|
| [14] |
X. Chen, S. Wehle, N. Kuzmanovic, et al., Acetylcholinesterase inhibitors with photoswitchable inhibition of beta-amyloid aggregation, ACS Chem. Neurosci. 5(2014) 377-389.
|
| [15] |
A. Mourot, T. Fehrentz, Y. Le Feuvre, et al., Rapid optical control of nociception with an ion-channel photoswitch, Nat. Methods 9(2012) 396-402.
|
| [16] |
W.A. Velema, M. van der Toorn, W. Szymanski, B.L. Feringa, Design, synthesis, and inhibitory activity of potent, photoswitchable mast cell activation inhibitors, J Med. Chem. 56(2013) 4456-4464.
|
| [17] |
M. Borowiak, W. Nahaboo, M. Reynders, et al., Photoswitchable inhibitors of microtubule dynamics optically control mitosis and cell death, Cell 162(2015) 403-411.
|
| [18] |
Z. Xu, L. Shi, D. Jiang, et al., Azobenzene modified imidacloprid derivatives as photoswitchable insecticides:steering molecular activity in a controllable manner, Sci. Rep. 5(2015) 13962.
|
| [19] |
J. Garcia-Amoros, M. Diaz-Lobo, S. Nonell, D. Velasco, Fastest thermal isomerization of an azobenzene for nanosecond photoswitching applications under physiological conditions, Angew. Chem. Int. Ed. 51(2012) 12820-12823.
|
| [20] |
J. Garcia-Amoros, E. Gomez, E. Valles, D. Velasco, Photo-controllable electronic switches based on azopyridine derivatives, Chem. Commun. 48(2012) 9080-9082.
|
| [21] |
P. Jeschke, R. Nauen, M.E. Beck, Nicotinic acetylcholine receptor agonists:a milestone for modern crop protection, Angew. Chem. Int. Ed. 52(2013) 9464-9485.
|
| [22] |
J.E. Casida, Curious about pesticide action, J. Agric. Food Chem. 59(2011) 2762-2769.
|
| [23] |
S. Kagabu, Discovery of imidacloprid and further developments from strategic molecular designs, J. Agric. Food Chem. 59(2011) 2887-2896.
|
|
|
|
