Citation: Li Shen, Song Run-Jiang, Wang Dong-Hui, Tian Xue, Shao Xu-Sheng, Li Zhong. Azopyridine-imidacloprid derivatives as photoresponsive neonicotinoids[J]. Chinese Chemical Letters, ;2016, 27(5): 635-639. doi: 10.1016/j.cclet.2016.03.033 shu

Azopyridine-imidacloprid derivatives as photoresponsive neonicotinoids

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

Corresponding author: Shao Xu-Sheng, shaoxusheng@ecust.edu.cn
Received Date: 24 February 2016
Revised Date: 15 March 2016
Accepted Date: 18 March 2016
Available Online: 31 May 2016

Figures(4)

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.
- Azopyridine,
- Photoresponsive,
- Imidacloprid,
- Solubility,
- Insecticide
1. [1]
  Gorostiza P., Isacoff E.. Optical switches and triggers for the manipulation of ion channels and pores[J]. Mol. Biosyst., 2007,3:686-704.
2. [2]
  Hamon F., Djedaini-Pilard F., Barbot F., Len C.. Azobenzenes-synthesis and carbohydrate applications[J]. Tetrahedron, 2009,65:10105-10123.
3. [3]
  Riggsbee C.W., Deiters A.. Recent advances in the photochemical control of protein function[J]. Trends Biotechnol., 2010,28:468-475.
4. [4]
  Fehrentz T., Schonberger M., Trauner D.. Optochemical genetics[J]. Angew. Chem. Int. Ed, 2011,50:12156-12182.
5. [5]
  Szymanski W., Beierle J.M., Kistemaker H.A., Velema W.A., Feringa B.L.. Reversible photocontrol of biological systems by the incorporation of molecular photoswitches[J]. Chem. Rev., 2013,113:6114-6178.
6. [6]
  Banghart M., Borges K., Isacoff E., Trauner D., Kramer R.H.. Light-activated ion channels for remote control of neuronal firing[J]. Nat. Neurosci., 2004,7:1381-1386.
7. [7]
  Samanta S., Beharry A.A., Sadovski O.. Photoswitching azo compounds in vivo with red light[J]. J. Am. Chem. Soc., 2013,135:9777-9784.
8. [8]
  Velema W.A., Szymanski W., Feringa B.L.. Photopharmacology:beyond proof of principle[J]. J. Am. Chem. Soc., 2014,136:2178-2191.
9. [9]
  Broichhagen J., Frank J.A., Trauner D.. A roadmap to success in photopharmacology[J]. Acc. Chem. Res., 2015,48:1947-1960.
10. [10]
  Velema W.A., van der Berg J.P., Hansen M.J.. Optical control of antibacterial activity[J]. Nat. Chem., 2013,5:924-928.
11. [11]
  Yue L., Pawlowski M., Dellal S.S.. Robust photoregulation of GABA_A receptors by allosteric modulation with a propofol analogue[J]. Nat. Commun, 2012,31095.
12. [12]
  Stein M., Middendorp S.J., Carta V.. Azo-propofols:photochromic potentiators of GABA (A) receptors[J]. Angew. Chem. Int. Ed., 2012,51:10500-10504.
13. [13]
  Broichhagen J., Schonberger M., Cork S.C.. Optical control of insulin release using a photoswitchable sulfonylurea[J]. Nat. Commun, 2014,55116.
14. [14]
  Chen X., Wehle S., Kuzmanovic N.. Acetylcholinesterase inhibitors with photoswitchable inhibition of beta-amyloid aggregation[J]. ACS Chem. Neurosci., 2014,5:377-389.
15. [15]
  Mourot A., Fehrentz T., Le Feuvre Y.. Rapid optical control of nociception with an ion-channel photoswitch[J]. Nat. Methods, 2012,9:396-402.
16. [16]
  Velema W.A., van der Toorn M., Szymanski W., Feringa B.L.. Design, synthesis, and inhibitory activity of potent, photoswitchable mast cell activation inhibitors[J]. J Med. Chem., 2013,56:4456-4464.
17. [17]
  Borowiak M., Nahaboo W., Reynders M.. Photoswitchable inhibitors of microtubule dynamics optically control mitosis and cell death[J]. Cell, 2015,162:403-411.
18. [18]
  Xu Z., Shi L., Jiang D.. Azobenzene modified imidacloprid derivatives as photoswitchable insecticides:steering molecular activity in a controllable manner[J]. Sci. Rep, 2015,513962.
19. [19]
  Garcia-Amoros J., Diaz-Lobo M., Nonell S., Velasco D.. Fastest thermal isomerization of an azobenzene for nanosecond photoswitching applications under physiological conditions[J]. Angew. Chem. Int. Ed., 2012,51:12820-12823.
20. [20]
  Garcia-Amoros J., Gomez E., Valles E., Velasco D.. Photo-controllable electronic switches based on azopyridine derivatives[J]. Chem. Commun., 2012,48:9080-9082.
21. [21]
  Jeschke P., Nauen R., Beck M.E.. Nicotinic acetylcholine receptor agonists:a milestone for modern crop protection[J]. Angew. Chem. Int. Ed., 2013,52:9464-9485.
22. [22]
  Casida J.E.. Curious about pesticide action[J]. J. Agric. Food Chem., 2011,59:2762-2769.
23. [23]
  Kagabu S.. Discovery of imidacloprid and further developments from strategic molecular designs[J]. J. Agric. Food Chem., 2011,59:2887-2896.
1. [1]
  Zhe Li , Ping-Zhao Liang , Li Xu , Fei-Yu Yang , Tian-Bing Ren , Lin Yuan , Xia Yin , Xiao-Bing Zhang . Three positive charge nonapoptotic-induced photosensitizer with excellent water solubility for tumor therapy. Chinese Chemical Letters, 2024, 35(8): 109190-. doi: 10.1016/j.cclet.2023.109190

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(700)
HTML views(31)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return