Investigation of the in vitro toxicological properties of the synthetic cannabimimetic drug CP-47,497-C8

Toxicology and Applied Pharmacology

Volumn 277, Issue 2, 2014, Pages 164-171

  Koller, Verena J ^a   Auwärter, Volker ^b   Grummt, Tamara ^c   Moosmann, Bjoern ^b   Mišík, Miroslav ^a   Knasmüller, Siegfried ^a  

^a MEDICAL UNIVERSITY OF VIENNA   (Austria)

^b UNIVERSITY OF FREIBURG   (Germany)

^c German Federal Environmental Agency Bad Elster Branch   (Germany)

Author keywords

Comet assay; CP 47,497 C8; Cytokinesis block micronucleus (CBMN) cytome assay; Cytotoxicity; Genotoxicity; Synthetic cannabinoid

Indexed keywords

CANNABICYCLOHEXANOL; CANNABINOID RECEPTOR AGONIST; CAS 70434 92 3; CYCLOHEXANOL DERIVATIVE; DNA BASE; LACTATE DEHYDROGENASE; SULFORHODAMINE B; UNCLASSIFIED DRUG;

AMES TEST; ARTICLE; BONE MARROW CELL; CELL STRAIN HEPG2; CHEEK; CHROMOSOME DAMAGE; COMET ASSAY; CONTROLLED STUDY; CYTOTOXICITY ASSAY; DNA DAMAGE; DRUG CYTOTOXICITY; GENE MUTATION; HUMAN; HUMAN CELL; IN VITRO STUDY; MEMBRANE DAMAGE; MICRONUCLEUS TEST; PROTEIN SYNTHESIS; XTT ASSAY;

COMET ASSAY; CP-47,497-C8; CYTOKINESIS-BLOCK MICRONUCLEUS (CBMN) CYTOME ASSAY; CYTOTOXICITY; GENOTOXICITY; SYNTHETIC CANNABINOID;

CANNABINOIDS; CELL MEMBRANE; CELL SURVIVAL; COMET ASSAY; CYCLOHEXANOLS; DNA DAMAGE; DOSE-RESPONSE RELATIONSHIP, DRUG; GENES, REPORTER; HEP G2 CELLS; HUMANS; LIVER; MICRONUCLEI, CHROMOSOME-DEFECTIVE; MICRONUCLEUS TESTS; MOUTH MUCOSA; MUTATION; PROTEIN BIOSYNTHESIS; RECEPTORS, ESTROGEN; RISK ASSESSMENT; SALMONELLA TYPHIMURIUM; TRANSFECTION;

EID: 84899138271     PISSN: 0041008X     EISSN: 10960333     Source Type: Journal    
DOI: 10.1016/j.taap.2014.03.014     Document Type: Article

References (38)

1. Auwärter V., Dresen S., Weinmann W., Muller M., Pütz M., Ferreiros N. 'Spice' and other herbal blends: harmless incense or cannabinoid designer drugs?. J. Mass Spectrom. 2009, 44:832-837.
2. Bologov A., Gafni M., Keren O., Sarne Y. Dual neuroprotective and neurotoxic effects of cannabinoid drugs in vitro. Cell. Mol. Neurobiol. 2011, 31:195-202.
3. Brosin A., Wolf V., Mattheus A., Heise H. Use of XTT-assay to assess the cytotoxicity of different surfactants and metal salts in human keratinocytes (HaCaT). A feasible method for in vitro testing of skin irritants. Acta Derm. Venereol. 1997, 77:26-28.
4. Collins A.R. The comet assay for DNA damage and repair: principles, applications, and limitations. Mol. Biotechnol. 2004, 26:249-261.
5. Collins A., Dušinská M. Oxidation of cellular DNA measured with the comet assay. Oxidative Stress Biomarkers and Antioxidant Protocols 2002, 147-160. Humana Press Inc., Totowa. D. Armstrong (Ed.).
6. Dresen S., Ferreiros N., Pütz M., Westphal F., Zimmermann R., Auwärter V. Monitoring of herbal mixtures potentially containing synthetic cannabinoids as psychoactive compounds. J. Mass Spectrom. 2010, 45:1186-1194.
7. Ehrlich V., Darroudi F., Uhl M., Steinkellner H., Zsivkovits M., Knasmueller S. Fumonisin B(1) is genotoxic in human derived hepatoma (HepG2) cells. Mutagenesis 2002, 17:257-260.
8. Fenech M. Cytokinesis-block micronucleus cytome assay. Nat. Protoc. 2007, 2:1084-1104.
9. Fluckiger-Isler S., Kamber M. Direct comparison of the Ames microplate format (MPF) test in liquid medium with the standard Ames pre-incubation assay on agar plates by use of equivocal to weakly positive test compounds. Mutat. Res. 2012, 747:36-45.
10. Fotakis G., Timbrell J.A. In vitro cytotoxicity assays: comparison of LDH, neutral red, MTT and protein assay in hepatoma cell lines following exposure to cadmium chloride. Toxicol. Lett. 2006, 160:171-177.
11. Han K.H., Lim S., Ryu J., Lee C.W., Kim Y., Kang J.H., Kang S.S., Ahn Y.K., Park C.S., Kim J.J. CB1 and CB2 cannabinoid receptors differentially regulate the production of reactive oxygen species by macrophages. Cardiovasc. Res. 2009, 84:378-386.
12. Henrich R.T., Nogawa T., Morishima A. In vitro induction of segregational errors of chromosomes by natural cannabinoids in normal human lymphocytes. Environ. Mutagen. 1980, 2:139-147.
13. Kneisel S., Auwärter V. Analysis of 30 synthetic cannabinoids in serum by liquid chromatography-electrospray ionization tandem mass spectrometry after liquid-liquid extraction. J. Mass Spectrom. 2012, 47:825-835.
14. Koller V.J., Auwärter V., Zlabinger G., Knasmüller S. Assessment of toxicological properties and establishment of risk profiles - genotoxic properties of selected spice compounds. First International Conference on Toxicity, Risk Profiles, Legal Control and Prevalence of Synthetic Cannabinoids; International Conference on SPICE Prevention Issues, Frankfurt am Main, Germany, pp 2012.
15. Koller V.J., Furhacker M., Nersesyan A., Misik M., Eisenbauer M., Knasmueller S. Cytotoxic and DNA-damaging properties of glyphosate and Roundup in human-derived buccal epithelial cells. Arch. Toxicol. 2012, 86:805-813.
16. Lutz W.K. A true threshold dose in chemical carcinogenesis cannot be defined for a population, irrespective of the mode of action. Hum. Exp. Toxicol. 2000, 19:566-568. (discussion 571-562).
17. Maines M.D. In Vitro Methods for Detecting Cytotoxicity in Current Protocols in Toxicology 1998, John Wiley & Sons, Inc., Hoboken, NJ, USA.
18. Maron D.M., Ames B.N. Revised methods for the Salmonella mutagenicity test. Mutat. Res. 1983, 113:173-215.
19. Moller P. The alkaline comet assay: towards validation in biomonitoring of DNA damaging exposures. Basic Clin. Pharmacol. Toxicol. 2006, 98:336-345.
20. Moosmann B., Kneisel S., Wohlfarth A., Brecht V., Auwärter V. A fast and inexpensive procedure for the isolation of synthetic cannabinoids from 'Spice' products using a flash chromatography system. Anal. Bioanal. Chem. 2012, 405:3929-3935.
21. Muller M., Strand S., Hug H., Heinemann E.M., Walczak H., Hofmann W.J., Stremmel W., Krammer P.H., Galle P.R. Drug-induced apoptosis in hepatoma cells is mediated by the CD95 (APO-1/Fas) receptor/ligand system and involves activation of wild-type p53. J. Clin. Invest. 1997, 99:403-413.
22. Repetto G., del Peso A., Zurita J.L. Neutral red uptake assay for the estimation of cell viability/cytotoxicity. Nat. Protoc. 2008, 3:1125-1131.
23. Rupniak H.T., Rowlatt C., Lane E.B., Steele J.G., Trejdosiewicz L.K., Laskiewicz B., Povey S., Hill B.T. Characteristics of four new human cell lines derived from squamous cell carcinomas of the head and neck. J. Natl. Cancer Inst. 1985, 75:621-635.
24. Seely K.A., Lapoint J., Moran J.H., Fattore L. Spice drugs are more than harmless herbal blends: a review of the pharmacology and toxicology of synthetic cannabinoids. Prog. Neuropsychopharmacol. Biol. Psychiatry 2012.
25. Skehan P., Storeng R., Scudiero D., Monks A., McMahon J., Vistica D., Warren J.T., Bokesch H., Kenney S., Boyd M.R. New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst. 1990, 82:1107-1112.
26. Sonneveld E., Jansen H.J., Riteco J.A., Brouwer A., van der Burg B. Development of androgen- and estrogen-responsive bioassays, members of a panel of human cell line-based highly selective steroid-responsive bioassays. Toxicol. Sci. 2005, 83:136-148.
27. Takeda S., Yamaori S., Motoya E., Matsunaga T., Kimura T., Yamamoto I., Watanabe K. Delta(9)-tetrahydrocannabinol enhances MCF-7 cell proliferation via cannabinoid receptor-independent signaling. Toxicology 2008, 245:141-146.
28. Teske J., Weller J.P., Fieguth A., Rothamel T., Schulz Y., Troger H.D. Sensitive and rapid quantification of the cannabinoid receptor agonist naphthalen-1-yl-(1-pentylindol-3-yl)methanone (JWH-018) in human serum by liquid chromatography-tandem mass spectrometry. J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 2010, 878:2659-2663.
29. Thakur G.A., Nikas S.P., Makriyannis A. CB1 cannabinoid receptor ligands. Mini-Rev. Med. Chem. 2005, 5:631-640.
30. Tice R.R., Agurell E., Anderson D., Burlinson B., Hartmann A., Kobayashi H., Miyamae Y., Rojas E., Ryu J.C., Sasaki Y.F. Single cell gel/comet assay: guidelines for in vitro and in vivo genetic toxicology testing. Environ. Mol. Mutagen. 2000, 35:206-221.
31. Tomiyama K., Funada M. Cytotoxicity of synthetic cannabinoids found in "Spice" products: the role of cannabinoid receptors and the caspase cascade in the NG 108-15 cell line. Toxicol. Lett. 2011, 207:12-17.
32. Uchiyama N., Kikura-Hanajiri R., Goda Y. Identification of a novel cannabimimetic phenylacetylindole, cannabipiperidiethanone, as a designer drug in a herbal product and its affinity for cannabinoid CB(1) and CB(2) receptors. Chem. Pharm. Bull. (Tokyo) 2011, 59:1203-1205.
33. UNODC World Drug Report 2013 2013, pp., United Nations Publication, (Sales No. E.13.XI.16).
34. van der Burg B., Winter R., Weimer M., Berckmans P., Suzuki G., Gijsbers L., Jonas A., van der Linden S., Witters H., Aarts J., Legler J., Kopp-Schneider A., Bremer S. Optimization and prevalidation of the in vitro ERalpha CALUX method to test estrogenic and antiestrogenic activity of compounds. Reprod. Toxicol. 2010, 30:73-80.
35. Vara D., Salazar M., Olea-Herrero N., Guzman M., Velasco G., Diaz-Laviada I. Anti-tumoral action of cannabinoids on hepatocellular carcinoma: role of AMPK-dependent activation of autophagy. Cell Death Differ. 2011, 18:1099-1111.
36. Vichai V., Kirtikara K. Sulforhodamine B colorimetric assay for cytotoxicity screening. Nat. Protoc. 2006, 1:1112-1116.
37. von Bueren A.O., Schlumpf M., Lichtensteiger W. Delta(9)-tetrahydrocannabinol inhibits 17beta-estradiol-induced proliferation and fails to activate androgen and estrogen receptors in MCF7 human breast cancer cells. Anticancer Res. 2008, 28:85-89.
38. Zimmerman S., Zimmerman A.M. Genetic effects of marijuana. Int. J. Addict. 1990, 25:19-33.