Cantharidin and Its anhydride-modified derivatives: Relation of structure to insecticidal activity

International Journal of Molecular Sciences

Volumn 14, Issue 1, 2013, Pages 1-16

  Sun, Wenbo ^a   Liu, Zhongyi ^a   Zhang, Yalin ^a  

^a NORTHWEST A F UNIVERSITY   (China)

Author keywords

Anhydride ring opening; Cantharidin; Derivatives; Larvicidal activity; Structure activity relationship; Synthesis

Indexed keywords

ACID ANHYDRIDE; CANTHARIDIN; CANTHARIDIN DERIVATIVE; DICARBOXYLIC ACID; INSECTICIDE; LARVICIDAL AGENT; NORCANTHARIDIN; NORCANTHARIDIN DERIVATIVE; PHTHALIMIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; INFRARED RADIATION; INSECTICIDAL ACTIVITY; LC 50; MASS SPECTROMETRY; MELTING POINT; NONHUMAN; PESTICIDE SPRAYING; PLUTELLA XYLOSTELLA; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; ANIMAL; BIOASSAY; CHEMISTRY; DRUG EFFECTS; LARVA; MOTH; SYNTHESIS;

PLUTELLA XYLOSTELLA;

ANHYDRIDES; ANIMALS; BIOLOGICAL ASSAY; CANTHARIDIN; INSECTICIDES; LARVA; MOTHS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84872171133     PISSN: 16616596     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms14010001     Document Type: Article

References (24)

1. Kuo, J.H.; Chu, Y.L.; Yang, J.S.; Lin, J.P.; Lai, K.C.; Kuo, H.M.; Hsia, T.C.; Chung, J.G. Cantharidin induces apoptosis in human bladder cancer TSGH 8301 cells through mitochondria-dependent signal pathways. Int. J. Oncol. 2010, 37, 1243-1250.
2. Huang, W.W.; Ko, S.W.; Tsai, H.Y.; Chung, J.G.; Chiang, J.H.; Chen, K.T.; Chen, Y.C.; Chen, Y.F.; Yang, J.S. Cantharidin induces G2/M phase arrest and apoptosis in human colorectal cancer colo 205 cells through inhibition of CDK1 activity and caspase-dependent signaling pathways. Int. J. Oncol. 2011, 38, 1067-1073.
3. Morihiko, S.; Tomonori, N.; Hideo, U.; Yasuo, I.; Masahiro, K. Cantharidin induces apoptosis of human multiple myeloma cells via inhibition of the JAK/STAT pathway. Cancer Sci. 2008, 99, 1820-1826.
4. Chen, L.P.; Yang, B.D.; Zhang, Z.Y.; Wang, J.Z.; Sun, S.L. Effects of cantharidin on insect cell Spex-VII and Sf9. J. Beijing Univ. Agric. 2008, 23, 17-20.
5. Carrel, J.E.; Eisner, T. Cantharidin: Potent feeding deterrent to insects. Science 1974, 183, 755-757.
6. Li, X.F.; Chen, X.S.; Hou, X.H. The toxicity effect of cantharidin on six pests. Guizhou Agric. Sci. 2008, 36, 65-66.
7. Liu, R.R.; Ma, Y.; Ma, Z.Q.; Zhang, Y.L. Bioactivity of cantharidin against eleven pests. J. Northwest AF Univ. 2010, 38, 181-185.
8. Lu, B.L. Pathological changes following the administration of cantharidin to Leucania separata (Walker). Acta Entomol. Sin. 1964, 13, 824-834.
9. Zhang, Y.L.; Zhou, Y.; Zhang, Z.Y. Effect of cantharidin on the midgut of the orient armyworm (Mythimna separata) and diamondback moth (Plutella xylostella). Acta Entomol. Sin. 2003, 46, 272-276.
10. Chen, L.P.; Yang, B.D.; Zhang, Z.Y.; Zhang, A.H.; Zhang, Z.M.; Zhang, L.X.; Sun, S.L. Effect of cantharidin on the integument structure of Plutella xylostella. Entomol. Knowl. 2011, 48, 1779-1785.
11. Ma, Y.; Liu, R.R.; Ma, Z.Q.; Zhang, Y.L. Effects of cantharidin on four metabolizing enzymes and PPO in Mythimna separata (Walker) (Lepidoptera Noctuidae). Acta Entomol. Sin. 2010, 53, 870-875.
12. Srork, G.; Tamelen, E.; Friedman, L.J.; Burgstahler, A.W. Cantharidin. A stereospecific total synthesis. J. Am. Chem. Soc. 1951, 73, 4501.
13. Srork, G.; Tamelen, E.; Friedman, L.J.; Burgstahler, A.W. Stereospecific synthesis of cantharidin. J. Am. Chem. Soc. 1953, 75, 384-392.
14. Dauben, W.G.; Kessel, C.R.; Takemura, K.H. Simple, efficient total synthesis of cantharidin via a high-pressure Diels-Alder reaction. J. Am. Chem. Soc. 1980, 102, 6893-6894.
15. Hill, T.A.; Stewart, S.G.; Ackland, S.P.; Gilbert, J.; Sauer, B.; Sakoff, J.A.; McCluskey, A. Norcantharimides, synthesis and anticancer activity: Synthesis of new norcantharidin analogues and their anticancer evaluation. Bioorg. Med. Chem. 2007, 15, 6126-6134.
16. Hill, T.A.; Stewart, S.G.; Gordon, C.P.; Ackland, S.P.; Gilbert, J.; Sauer, B.; Sakoff, J.A.; McCluskey, A. Norcantharidin analogues: Synthesis, anticancer activity and protein phosphatase 1 and 2A inhibition. ChemMedChem 2008, 3, 1878-1892.
17. Yue, H.Y.; Liu, Z.F. A new synthetic process of phthalimide. Fine Chem. Inter. 2004, 35, 44-45.
18. Bajsa, J.; Duke, S.O.; Tekwani, B.L. Plasmodium falciparum serine/threonine phosphoprotein phosphatases (PPP): From housekeeper to the "Holy Grail". Curr. Drug Targets 2008, 9, 997-1012.
19. Lin, X.H.; Walter, J.; Scheidmann, K.; Ohst, K.; Newport, J.; Walter, G. Protein phosphatase 2A is required for the initiation of chromosomal DNA replication. Proc. Natl. Acad. Sci. USA 1998, 95, 14693-14698.
20. Moorhead, G.B.; de Wever, V.; Templeton, G.; Kerk, D. Evolution of protein phosphatases in plants and animals. Biochem. J. 2009, 417, 401-409.
21. Bertini, I.; Calderone, V.; Fragai, M.; Luchinat, C.; Talluri, E. Structural basis of serine/threonine phosphatase inhibition by the archetypal small molecules cantharidin and norcantharidin. J. Med. Chem. 2009, 52, 4838-4843.
22. 3H] endothall thioanhydride binding site. Inhibitor specificity of cantharidin and ATP analogues. Biochem. Pharmacol. 1993, 46, 1435-1443.
23. Finney, D.J. Probit Analysis, 2nd ed.; Cambridge University Press: Cambridge, UK, 1971; pp. 35-41.
24. Abbott, W.S. A method of computing the effectiveness of an insecticide. J. Econ. Entomol. 1925, 18, 265-267.