Cantharidin-based small molecules as potential therapeutic agents

Chemical Biology and Drug Design

Volumn 82, Issue 5, 2013, Pages 477-499

  Puerto Galvis, Carlos E ^a   Vargas Méndez, Leonor Y ^b   Kouznetsov, Vladimir V ^a  

^a UNIVERSIDAD INDUSTRIAL DE SANTANDER   (Colombia)

^b UNIVERSIDAD SANTO TOMÁS   (Colombia)

Author keywords

Anticancer activity; Blister beetles; Cantharidin analogs; Diels Alder cycloaddition reactions; Drug design and development; Protein phosphatases inhibitory activity

Indexed keywords

ACID ANHYDRIDE; CANTHARIDIN; CARBONYL DERIVATIVE; DICHLOROMETHANE; HETEROCYCLIC COMPOUND; MALEIC ANHYDRIDE; NORCANTHARIDIN; PALASONIN; PHOSPHOPROTEIN PHOSPHATASE 1; PHOSPHOPROTEIN PHOSPHATASE 2; THIOPHENE; UNCLASSIFIED DRUG;

ACUTE TOXICITY; ALKYLATION; ARYLATION; BEETLE; BIOLOGICAL ACTIVITY; BLISTER BEETLE; BUTEA; BUTEA FRONDOSA; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CYCLOADDITION; DIASTEREOISOMER; DIELS ALDER REACTION; HEMOLYMPH; HYDROGENATION; INTOXICATION; METABOLIC REGULATION; MICROWAVE IRRADIATION; NONHUMAN; OXIDATION; PRIORITY JOURNAL; PROTEIN DEPHOSPHORYLATION; PROTEIN PHOSPHORYLATION; RACEMIC MIXTURE; REDUCTION; REVIEW; SECRETORY PATHWAY; SIGNAL TRANSDUCTION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

ALNUS; MELOIDAE;

ANTICANCER ACTIVITY; BLISTER BEETLES; CANTHARIDIN ANALOGS; DIELS-ALDER CYCLOADDITION REACTIONS; DRUG DESIGN AND DEVELOPMENT; PROTEIN PHOSPHATASES INHIBITORY ACTIVITY;

ANIMALS; ANTINEOPLASTIC AGENTS; BEETLES; BICYCLO COMPOUNDS, HETEROCYCLIC; CANTHARIDIN; CELL SURVIVAL; ENZYME ACTIVATION; HUMANS; NEOPLASMS; PHOSPHOPROTEIN PHOSPHATASES;

EID: 84885832826     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/cbdd.12180     Document Type: Review

References (108)

1. Newman D.J., Cragg G.M., Snader K.M. (2003) Natural products as sources of new drugs over the period 1981-2002. J Nat Prod;66:1022-1037.
2. Newman D.J., Cragg G.M. (2007) Natural products as sources of new drugs over the last 25 years. J Nat Prod;70:461-477.
3. Tan D.S. (2007) Expanding the scope of chemical synthesis-diversity-oriented synthesis. In: Schreiber S.L., Kapoor T.M., Wess G., editors. Chemical Biology. From Small Molecules to System Biology and Drug Design, vol. 2. Weinheim, Germany: Wiley-VCH; p. 483-518.
4. Clardy J., Walsh C. (2004) Lessons from natural molecules. Nature;432:829-837.
5. Feher M., Schmidt J.M. (2003) Property distributions: differences between drugs, natural products, and molecules from combinatorial chemistry. J Chem Inf Comput Sci;43:218-227.
6. Beghyn T., Deprez-Poulain R., Willand N., Folleas B., Deprez B. (2008) Natural compounds: leads or ideas? Bioinspired molecules for drug discovery. Chem Biol Drug Des;72:3-15.
7. Piggott A.M., Karuso P. (2004) Quality, not quantity: the role of natural products and chemical proteomics in modern drug discovery. Comb Chem High Through-put Screen;7:607-630.
8. Terstappen G.C., Schlüpen C., Raggiaschi R., Gaviraghi G. (2007) Target deconvolution strategies in drug discovery. Nat Rev Drug Discov;6:891-903.
9. Osada H. (1998) Bioprobes for investigating cell cycle control. J Antibiot;51:973-981.
10. Osada H. (2000) Trends in bioprobe research. In: Osada H., editor. Bioprobes: Biochemical Tools for Investigating Cell Function. Tokyo, Japan: Springer-Verlag; p. 1-14.
11. McCluskey A., Sim A.T.R., Jennette A., Sakoff J.A. (2002) Serine-threonine protein phosphatase inhibitors: development of potential therapeutic strategies. J Med Chem;45:1151-1175.
12. McCluskey A., Ackland S.P., Gardiner E., Walkom C.C., Sakoff J.A. (2001) The inhibition of protein phosphatases 1 and 2A: a new target for rational anti-cancer drug design? Anticancer Drug Des;16:291-303.
13. Griffith R., Brown M.N., McCluskey A., Ashman L.K. (2006) Small molecule inhibitors of protein kinases in cancer- how to overcome resistance. Mini Rev Med Chem;6:1101-1110.
14. Bologna M.A., Pinto J.D. (2001) Phylogenetic studies of Meloidae (Coleoptera), with emphasis on the evolution of phorsey. Syst Entomol;26:33-72.
15. Ghoneim K.S. (2013) Embryonic and postembryonic development of blister beetles (Coleoptera: Meloidae) in the world: a synopsis. Int J Biol Sci;2:6-18.
16. Wang G.S. (1989) Medical uses of mylabris in ancient China and recent studies. J Ethnopharmacol;26:147-162.
17. Stork G., van Tamelen E.E., Friedman L.J., Busgstahler A.W. (1953) A stereospecific synthesis of cantharidin. J Am Chem Soc;75:384-392.
18. Gadamer J. (1914) The constitution of cantharidin. Arch Pharm;252:609-632. Cited by Stork G., van Tamelen E.E., Friedman L.J., Busgstahler A.W. (1953) A stereospecific Synthesis of Cantharidin. J Am Chem Soc;75:384-392.
19. Sheppeek H.J.E., Gauss C.M., Chamberlin A.R. (1997) Inhibition of the ser-thr phosphatases PP1 and PP2A by naturally occurring toxins. Bioorg Med Chem Lett;5:1739-1750.
20. Karras D.J., Farrell S.E., Harrigan R.A., Henretig F.M., Gealt L. (1996) Poisoning from "Spanish fly" (Cantharidin). Am J Emerg Med;14:478-483.
21. Raj R.K., Kurup P.A. (1967) Isolation and characterization of palasonin, an anthelmintic principle of the seeds of Butea frondosa. Indian J Chem;5:86-87.
22. Raj R.K., Kurup P.A. (1967) Mode of action of palasonin. I. Effect of palasonin on total glycogen and reducing sugar contents, and glycogen synthetase activity of Ascaris lumbricoides. Indian J Biochem;42:90-93.
23. Bochis R.J., Fisher M.H. (1968) The structure of palasonin. Tetrahedron Lett;9:1971-1974.
24. Rydberg D.B., Meinwald J. (1996) Synthesis of (±)-palasonin. Tetrahedron Lett;37:1129-1132.
25. Fietz O., Dettner K., Görls H., Klemm K., Boland W. (2002) (R)-(+)-palasonin, a cantharidin-related plant toxin, also occurs in insect hemolymph and tissues. J Chem Ecol;28:1315-1327.
26. Mebs D., Pogoda W., Schneider M., Kauert G. (2009) Cantharidin and demethylcantharidin (Palasonin) content of blister beetles (Coleoptera: Meloidae) from Southern Africa. Toxicon;53:466-468.
27. Meinwald J. (2011) Natural molecules as molecular messengers. J Nat Prod;74:305-309.
28. Eisner T., Smedley S.R., Young D.K., Eisner M., Roach B., Meinwald J. (1996) Chemical basis of courtship in a beetle (Neopyrochroa flabellate): Cantharidin as precopulatory "enticing" agent. Proc Natl Acad Sci USA;93:6494-6498.
29. Meinwald J. (2009) The chemistry of biotic interactions in perspective: small molecules take center stage. J Org Chem;74:1813-1825.
30. Eisner T., Smedley S.R., Young D.K., Eisner M., Roach B., Meinwald J. (1996) Chemical basis of courtship in a beetle (Neopyrochroa flabellata): cantharidin as "nuptial gift". Proc Natl Acad Sci USA;93:6499-6505.
31. Guenther H., Ramstad E., Floss H.G. (1969) On the biosynthesis of cantharidin. J Pharm Sci;58:1274.
32. McCormick J.P., Carrel J.E., Doom J.P. (1986) Origin of oxygen atoms in cantharidin biosynthesized by beetles. J Am Chem Soc;108:8071-8074.
33. Yang P.Y., Chen M.F., Kao Y.H., Hu D.N., Chang F.R., Wu Y.C. (2011) Norcantharidin induces apoptosis of breast cancer cells: involvement of activities of mitogen activated protein kinases and signal transducers and activators of transcription. Toxicol In Vitro;25:699-707.
34. Chen Y.C., Chang S.C., Wu M.H., Chuang K.A., Tsai W.J., Kuo Y.C., Wu J.Y., Tsai W.J., Kuo Y.C. (2009) Norcantharidin reduced cyclins and cytokines production in human peripheral blood mononuclear cells. Life Sci;84:218-226.
35. Nakatani T., Konichi T., Miyahara K., Noda N. (2004) Three novel cantharidin-related compounds from the Chinese blister beetle, Mylabris phalerata PALL. Chem Pharm Bull;57:807-809.
36. Tseng I.J., Sheu S.Y., Li P.Y., Lee J.A., Ou K.L., Lee L.W. (2012) Synthesis and evaluation of cantharidinimides on human cancer cells. J Exp Clin Med;4:280-283.
37. von Bruchhausen F., Bersch H.W. (1929) Constitution of cantharidin. Arch Pharm;266:697-702.
38. Diels O., Alder K. (1929) Synthesis in the hydroaromatic series. II. Cantharidin. Ber;62:554-562.
39. Stork G., van Tamelen E.E., Friedman L.J., Busgstahler A.W. (1951) Cantharidin. A stereospecific total synthesis. J Am Chem Soc;73:4501.
40. Schenck G., Wirtz R. (1953) Eine weitere Synthese des Cantharidins. Naturwissenschaften;40:581.
41. Dauben W.G., Lam J.Y.L., Guo Z.R. (1996) Total synthesis of (-)-palasonin and (+)-palasonin and realated chemistry. J Org Chem;61:4816-4819.
42. Dauben W.G., Kessel C.R., Takemura K.H. (1980) Simple, efficient total synthesis of cantharidin via a high-pressure Diels-Alder reaction. J Am Chem Soc;102:6893-6894.
43. Grieco P.A., Nunes J.J., Gaul M.D. (1990) Dramatic rate accelerations of Diels-Alder reactions in 5 m lithium perchlorat-diethyl ether: the cantharidin problem reexamined. J Am Chem Soc;112:4595-4596.
44. Filler R. (1993) Chapter 1: general introduction. In: Filler R., Kobayashi Y., Yagupolskii L.M., editors. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications. Amsterdam, Netherlands: Elsevier Science Publishers B.V.; p. 1-22.
45. Essers M., Wibbeling B., Haufe G. (2001) Synthesis of the first fluorinated cantharidin analogues. Tetrahedron Lett;42:5429-5433.
46. McCluskey A., Keane M.A., Sim A.T.R., Walkom C.C., Young D.J., Bowyer M.C., Sakoff J.A. (2002) The first two cantharidin analogues displaying PP1 selectivity. Bioorg Med Chem Lett;12:391-393.
47. Hart M.E., Chamberlin R., Walkom C., Sakoff J.A., McCluskey A. (2004) Modified norcantharidins: synthesis, protein phosphatases 1 and 2A inhibition, and anticancer activity. Bioorg Med Chem Lett;14:1969-1973.
48. Tatlock J.H., Linton M.A., Hou X.J., Kissinger C.R., Pelletier L.A., Showalter R.E., Tempczyk A., Villafranca J.E. (1997) Structure-based design of novel calcineurin (PP2B) inhibitors. Bioorg Med Chem Lett;7:1007-1012.
49. 2. Green Chem;7:105-110.
50. Miyamoto H., Kimura T., Daikawa N., Tanaka N. (2003) Preparation of optically active cis-4-methylcyclohex-4-ene-1, 2-dicarboximides by a combination of Diels-Alder reaction and complexation with optically active hosts and enantioselective Diels-Alder reaction in inclusion crystals in a water suspension medium. Green Chem;5:57-59.
51. Shen Z.L., Cheong H.L., Lai Y.C., Loo W.Y., Loh T.P. (2012) Application of recyclable ionic liquid-supported imidazolidinone catalyst in enantioselective Diels-Alder reactions. Green Chem;14:2626-2630.
52. Kouznetsov V.V., Merchan Arenas D.R., Romero Bohórquez A.R. (2008) PEG-400 as green reaction medium for Lewis acid-promoted cycloaddition reactions with isoeugenol and anethole. Tetrahedron Lett;49:3097-3100.
53. Imperato G., Eibler E., Niedermaier J., König B. (2005) Low-melting sugar-urea-salt mixtures as solvents for Diels-Alder reactions. Chem Commun;9:1170-1172.
54. Tarleton M., Gilbert J., Sakoff J.A., McCluskey A. (2012) Synthesis and anticancer activity of a series of norcantharidin analogues. Eur J Med Chem;54:573-581.
55. de Jong R.S., Mulder N.H., Uges D.R.A., Sleijfer D.T., Hoppener F.J.P., Groen H.J.M., Willemse P.H.B., van der Graaf W.T.A., de Vries E.G.E. (1999) Phase I and pharmacokinetic study of the topoisomerase II catalytic inhibitor fostriecin. Br J Cancer;79:882-887.
56. Goh Y.W., Pool B.R., White J.M. (2008) Structural studies on cycloadducts of furan, 2-methoxyfuran, and 5-trimethylsilylcyclopentadiene with maleic anhydride and N-methylmaleimide. J Org Chem;73:151-156.
57. McCluskey A., Walkom C., Bowyer M.C., Ackland S.P., Gardiner E., Sakoff J.A. (2001) Cantharimides: a new class of modified cantharidin analogues inhibiting protein phosphatases 1 and 2A. Bioorg Med Chem Lett;11:2941-2946.
58. Hill T.A., Stewart S.G., Sauer B., Ackland S.P., Sakoff J.A., Gilbert J., McCluskey A. (2007) Norcantharimides, synthesis and anticancer activity: synthesis of new norcantharidin analogues and their anticancer evaluation. Bioorg Med Chem;15:6126-6134.
59. Kok S.H.L., Chui C.H., Lam W.S., Chen J., Tang J.C.O., Lau F.Y., Cheng G.Y.M., Wong R.S.M., Chan A.S.C. (2006) Induction of apoptosis on carcinoma cells by two synthetic cantharidin analogues. Int J Mol Med;17:151-157.
60. Kok S.H.L., Chui C.H., Lam W.S., Chen J., Tang J.C.O., Lau F.Y., Cheng G.Y.M., Wong R.S.M., Lai P.P.S., Leung T.W.T., Chan A.S.C. (2006) Apoptotic activity of a novel synthetic cantharidin analogue on hepatoma cell lines. Int J Mol Med;17:945-949.
61. Lung S.H., Chui C.H., Lam W.S., Chen J., Lau F.Y., Wong R.S.M., Cheng G.Y.M., Lai P.B.S., Leung T.W.T., Yu M.W.Y., Tanga J.C.O., Chana A.S.C. (2007) Synthesis and structure evaluation of a novel cantharimide and its cytotoxicity on SK-Hep-1 hepatoma cells. Bioorg Med Chem Lett;17:1155-1159.
62. Thaqi A., Scott J.L., Gilbert J., Sakoff J.A., McCluskey A. (2010) Synthesis and biological activity of Δ-5, 6-norcantharimides: importance of the 5, 6-bridge. Eur J Med Chem;45:1717-1723.
63. Rojas Ruiz F.A., Kouznetsov V.V. (2011) Property-based design and synthesis of new chloroquine hybrids via simple incorporation of 2-imino-thiazolidin-4-one or 1H-Pyrrol-2, 5-dione fragments on the 4-amino-7-chloroquinoline side chain. J Braz Chem Soc;22:1774-1781.
64. Sauer B., Gilbert J., Sakoff J.A., McCluskey A. (2009) Synthesis of 4-substituted-3-hydroxy-5-oxo-10-oxa-4-azatricyclo[5.2.1]dec-3-yl acetic acid ethyl esters as norcantharidin analogues. Lett Drug Des Discov;6:1-7.
65. Chen D.F., Zou Y., Li Y.Q., Cai Y.C., Xian L.J. (2008) Improved synthesis and characterization of l-histidine norcantharimide, a novel potent protein phosphatase 2A inhibitor. J Chin Pharm Sci;17:134-137.
66. Robertson M.J., Gordon C.P., Gilbert J., McCluskey A., Jennette A., Sakoff J.A. (2011) Norcantharimide analogues possessing terminal phosphate esters and their anti-cancer activity. Bioorg Med Chem;19:5734-5741.
67. Deng L.P., Liu F.M., Wang H.Y. (2005) 1, 3-Dipolar cycloaddition reaction of novel 5, 6-dehydronorcantharidin derivatives of substituted aromatic amines with potential antitumoral activities. J Heterocycl Chem;48:13-18.
68. Deng L., Hu Y. (2007) Synthesis of novel norcantharidin derivatives of substituted aromatic amines with improved 1, 3-dipolar cycloaddition. Synth Commun;37:157-163.
69. Goksu G., Öcal N., Kaufmann D.E. (2010) Reductive heck reactions of N-methyl-substituted tricyclic imides. Molecules;15:1302-1308.
70. Puerto Galvis C.E., Kouznetsov V.V. (2013) An unexpected formation of the novel 7-oxa-2-azabicyclo[2.2.1]hept-5-ene skeleton during the reaction of furfurylamine with maleimides and their bioprospection using zebrafish embryo model. Org Biomol Chem;11:407-411.
71. Li Y.M., Casida J.E. (1992) Cantharidin-binding protein: identification as protein phosphatase 2A. Proc Natl Acad Sci USA;89:11867-11870.
72. Hardie D.G. (2002) Protein Phosphorylation: A Practical Approach. New York, NY, USA: Oxford University Press; p. 1-65.
73. Shenolikar S. (1994) Protein serine/threonine phosphatases-new avenues for cell regulation. Annu Rev Cell Biol;10:55-86.
74. Zhang Z.Y. (2001) Protein tyrosine phosphatases: prospects for therapeutics. Curr Opin Chem Biol;5:416-423.
75. Cohen P. (2002) The origins of protein phosphorylation. Nat Cell Biol;4:E127-E130.
76. Moorhead G.B., De Wever V., Templeton G., Kerk D. (2009) Evolution of protein phosphatases in plants and animals. Biochem J;417:401-409.
77. McCluskey A., Sakoff J.A. (2001) Small molecule inhibitors of serine threonine protein phosphatases. Mini Rev Med Chem;1:43-55.
78. Gupta V., Ogawa A.K., Du X., Houk K.N., Armstrong R.W. (1997) A model for binding of structurally diverse natural product inhibitors of protein phosphatases PP1 and PP2A. J Med Chem;40:3199-3206.
79. Stenlund P.A., Frostell-Karlsson Å., Karlsson O.P. (2006) Studies of small molecule interactions with protein phosphatases using biosensor technology. Anal Biochem;353:217-225.
80. Twu N.F., Srinivasan R., Chou C.H., Wu L.S., Chiu C.H. (2012) Cantharidin and norcantharidin inhibit caprine luteal cell steroidogenesis in vitro. Exp Toxicol Pathol;64:37-44.
81. Janssens V., Goris J., Van Hoof C. (2005) PP2A: the expected tumor suppressor. Curr Opin Genet Dev;15:34-41.
82. Chen Y.J., Kuo C.D., Tsai Y.M., Yu C.C., Wang G.S., Liao H.F. (2008) Norcantharidin induces anoikis through Jun-N-terminal kinase activation in CT26 colorectal cancer cells. Anticancer Drugs;19:55-64.
83. Schweyer S., Bachem A., Bremmer F., Steinfelder H.J., Soruri A., Wagner W., Pottek T., Thelen P., Hopker W.W., Radzun H.J., Fayyazi A. (2007) Expression and function of protein phosphatase PP2A in malignant testicular germ cell tumours. J Pathol;213:72-81.
84. Li W., Chen Z., Gong F.R., Zong Y., Chen K., Li D.M., Yin H., Duan W.M., Miao Y., Tao M., Han X., Xu Z.K. (2011) Growth of the pancreatic cancer cell line PANC-1 is inhibited by protein phosphatase 2A inhibitors through overactivation of the c-Jun N-terminal kinase pathway. Eur J Cancer;47:2654-2664.
85. Tresch S., Schmotz J., Grossmann K. (2011) Probing mode of action in plant cell cycle by the herbicide endothall, a protein phosphatase inhibitor. Pestic Biochem Physiol;99:86-95.
86. Norbury C.J., Zhivotovsky B. (2004) DNA damage-induced apoptosis. Oncogene;23:2797-2808.
87. Slee E.A., O'Connor D.J., Lu X. (2004) To die or not to die: how does p53 decide? Oncogene;23:2809-2818.
88. Bertini I., Calderone V., Fragai M., Luchinat C., Talluri E. (2009) Structural basis of serine/threonine phosphatase inhibition by the archetypal small molecules cantharidin and norcantharidin. J Med Chem;52:4838-4843.
89. Knapp J., Boknik P., Huke S., Gombosova I., Linck B., Luss H., Muller F.U., Muller T., Nacke P., Schmitz W., Vahlensieck U., Neumann J. (1998) Contractility and inhibition of protein phosphatases by cantharidin. Gen Pharmacol;31:729-733.
90. Stewart S.G., Hill T.A., Gilbert J., Ackland S.P., Sakoff J.A., McCluskey A. (2007) Synthesis and biological evaluation of norcantharidin analogues: towards PP1 selectivity. Bioorg Med Chem;15:7301-7310.
91. Hill T.A., Stewart S.G., Sauer B., Gilbert J., Ackaland S.P., Sakoff J.A., McCluskey A. (2007) Heterocyclic substituted cantharidin and norcantharidin analogues - synthesis, protein phosphatase (1 and 2A) inhibition, and anti-cancer activity. Bioorg Med Chem Lett;17:3392-3397.
92. Moed L., Shwayder T.D., Chang M.W. (2001) Cantharidin revisited: a blistering defense of an ancient medicine. Arch Dermatol;137:1357-1360.
93. Sánchez-Barbudo I.S., Camarero P.R., García-Montijano M., Mateo R. (2012) Possible cantharidin poisoning of a great bustard (Otis tarda). Toxicon;59:100-103.
94. Wei C., Teng Y., Wang B., Zhang X., Yuan G., Liu X., Li R., Guo R. (2011) Separation and identification of norcantharidin metabolites in vivo by GC-MS method. J Chromatogr B;879:1741-1747.
95. Helman R.G., Edwards W.C. (1997) Clinical features of blister beetle poisoning in equids. J Am Vet Med Assoc;211:1018-1021.
96. Tagwireyi D., Ball D.E., Loga P.J., Moyo S. (2000) Cantharidin poisoning due to "Blister beetle" ingestion. Toxicon;38:1865-1869.
97. Chen Y.J., Chang W.M., Liu Y.W., Lee C.Y., Jang Y.H., Kuo C.D., Liao H.F. (2009) A small-molecule metastasis inhibitor, norcantharidin, downregulates matrix metalloproteinase-9 expression by inhibiting Sp1 transcriptional activity in colorectal cancer cells. Chem Biol Interact;181:440-446.
98. Hsieh C.H., Huang Y.C., Tsai T.H., Chen Y.J. (2011) Cantharidin modulates development of human monocyte-derived dendritic cells. Toxicol In Vitro;25:1740-1747.
99. Bajsa J., McCluskey A., Gordon C.P., Stewart S.G., Sahu R., Duke S.O., Tekwan B.L. (2010) The antiplasmodial activity of norcantharidin analogs. Bioorg Med Chem Lett;20:6688-6695.
100. Ghaffarifar F. (2010) Leishmania major: in vitro and in vivo anti-leishmanial effect of cantharidin. Exp Parasitol;126:126-129.
101. Campbell B.E., Hofmann A., McCluskey A., Gasser R.B. (2011) Serine/threonine phosphatases in socioeconomically important parasitic nematodes-prospects as novel drug targets? Biotechnol Adv;29:28-39.
102. Campbell B.E., Tarleton M., Gordon C.P., Sakoff J.A., Gilbert J., McCluskey A., Gasser R.B. (2011) Norcantharidin analogues with nematocidal activity in Haemonchus contortus. Bioorg Med Chem Lett;21:3277-3281.
103. Fukamachi T., Chiba Y., Wang X., Saito H., Tagawa M., Kobayashi H. (2010) Tumor specific low pH environments enhance the cytotoxicity of lovastatin and cantharidin. Cancer Lett;297:182-189.
104. Wang G.C., Xiao J., Yu L., Li J.S., Cui J.R., Wang R.Q., Ran F.X. (2004) Synthesis, crystal structures and in vitro antitumor activities of some arylantimony derivatives of analogues of demethylcantharimide. J Organomet Chem;689:1631-1638.
105. Zhang J., Lawrance G.A., Chau N., Robinson P.J., McCluskey A. (2008) From Spanish fly to room-temperature ionic liquids (RTILs): synthesis, thermal stability and inhibition of dynamin 1 GTPase by a novel class of RTILs. New J Chem;32:28-36.
106. Fan Z., Wenzhong Z., Qiuyue L., Weidong G., Lingling Z., Shikun L. (2011) Synthesis, characterization and DNA binding of the complexes of rare earth with phenanthroline and demethylcantharate. J Rare Earths;29:297-302.
107. Zeng Q., Sun M. (2009) Poly(lactide-co-glycolide) nanoparticles as carriers for norcantharidin. Mater Sci Eng, C;29:708-713.
108. Yun-jie D., Chun-yan Z. (2012) Genomic study of the absorption mechanism of cantharidin solid dispersion and its solid dispersion. Colloids Surf A;415:295-301.