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Volumn 58, Issue 5, 2015, Pages 2256-2264

Selective, nontoxic CB2 cannabinoid o-quinone with in vivo activity against triple-negative breast cancer

Author keywords

[No Author keywords available]

Indexed keywords

7 (1',1' DIMETHYLHEPTYL) 1 ETHYL 1,4 DIHYDRO 4,4 DIMETHYLCHROMENO[4,3 C]PYRAZOLE 8,9 DIONE; 7 (1',1' DIMETHYLHEPTYL) 1,4 DIHYDRO 4,4 DIMETHYLCHROMENO[4,3 C]PYRAZOLE 6,9 DIONE; 7 (1',1' DIMETHYLHEPTYL) 1,4 DIHYDRO 4,4 DIMETHYLCHROMENO[4,3 C]PYRAZOLE 8,9 DIONE; 7 (1',1' DIMETHYLHEPTYL) 2,4 DIHYDRO 4,4 DIMETHYLCHROMENO[4,3 C]PYRAZOLE 6,9 DIONE; 7 (1',1' DIMETHYLHEPTYL) 2,4 DIHYDRO 4,4 DIMETHYLCHROMENO[4,3 C]PYRAZOLE 8,9 DIONE; ANTINEOPLASTIC AGENT; CANNABINOID 2 RECEPTOR; CANNABINOID QUINONE; CASPASE 3; UNCLASSIFIED DRUG; 7-(1',1'-DIMETHYLHEPTYL)-1-ETHYL-1,4-DIHYDRO-4,4-DIMETHYLCHROMENO(4,3-C)PYRAZOLE-8,9-DIONE; BENZOPYRAN DERIVATIVE; BENZOQUINONE; BENZOQUINONE DERIVATIVE; CANNABINOID; MESSENGER RNA; PYRAZOLE DERIVATIVE;

EID: 84924709736     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.5b00078     Document Type: Article
Times cited : (34)

References (50)
  • 1
    • 0035822323 scopus 로고    scopus 로고
    • Cannabinoids for control of chemotherapy induced nausea and vomiting: Quantitative systematic review
    • Tramer, M. R.; Carroll, D.; Campbell, F.; Reynolds, D. J.; Moore, R.; McQuay, H. J. Cannabinoids for control of chemotherapy induced nausea and vomiting: quantitative systematic review Br. Med. J. 2001, 323, 16-21
    • (2001) Br. Med. J. , vol.323 , pp. 16-21
    • Tramer, M.R.1    Carroll, D.2    Campbell, F.3    Reynolds, D.J.4    Moore, R.5    McQuay, H.J.6
  • 2
    • 84892899650 scopus 로고    scopus 로고
    • Regulation of nausea and vomiting by cannabinoids and the endocannabinoid system
    • Sharkey, K. A.; Darmani, N. A.; Parker, L. A. Regulation of nausea and vomiting by cannabinoids and the endocannabinoid system Eur. J. Pharmacol. 2014, 722, 134-146
    • (2014) Eur. J. Pharmacol. , vol.722 , pp. 134-146
    • Sharkey, K.A.1    Darmani, N.A.2    Parker, L.A.3
  • 3
    • 84883341895 scopus 로고    scopus 로고
    • Critical appraisal of the potential use of cannabinoids in cancer management
    • Cridge, B. J.; Rosengren, R. J. Critical appraisal of the potential use of cannabinoids in cancer management Cancer Manage. Res. 2013, 5, 301-313
    • (2013) Cancer Manage. Res. , vol.5 , pp. 301-313
    • Cridge, B.J.1    Rosengren, R.J.2
  • 4
    • 84861530762 scopus 로고    scopus 로고
    • Towards the use of cannabinoids as antitumour agents
    • Velasco, G.; Sánchez, C.; Guzmán, M. Towards the use of cannabinoids as antitumour agents Nat. Rev. Cancer 2012, 12, 436-444
    • (2012) Nat. Rev. Cancer , vol.12 , pp. 436-444
    • Velasco, G.1    Sánchez, C.2    Guzmán, M.3
  • 5
    • 0142166330 scopus 로고    scopus 로고
    • Cannabinoids: Potential anticancer agents
    • Guzmán, M. Cannabinoids: potential anticancer agents Nat. Rev. Cancer 2003, 3, 745-755
    • (2003) Nat. Rev. Cancer , vol.3 , pp. 745-755
    • Guzmán, M.1
  • 6
    • 84906238485 scopus 로고    scopus 로고
    • Cannabinoids as therapeutic agents in cancer: Current status and future implications
    • Chakravarti, B.; Ravi, J.; Ganju, R. K. Cannabinoids as therapeutic agents in cancer: current status and future implications Oncotarget 2014, 5, 5852-5872
    • (2014) Oncotarget , vol.5 , pp. 5852-5872
    • Chakravarti, B.1    Ravi, J.2    Ganju, R.K.3
  • 7
    • 79960336157 scopus 로고    scopus 로고
    • The endocannabinoid system and cancer: Therapeutic implication
    • Guindon, J.; Hohmann, A. G. The endocannabinoid system and cancer: therapeutic implication Br. J. Pharmacol. 2011, 163, 1447-1463
    • (2011) Br. J. Pharmacol. , vol.163 , pp. 1447-1463
    • Guindon, J.1    Hohmann, A.G.2
  • 8
    • 84874658451 scopus 로고    scopus 로고
    • Receptor-dependent and receptor-independent endocannabinoid signaling: A therapeutic target for regulation of cancer growth
    • Van Dross, R.; Soliman, E.; Jha, S.; Johnson, T.; Mukhopadhyay, S. Receptor-dependent and receptor-independent endocannabinoid signaling: a therapeutic target for regulation of cancer growth Life Sci. 2013, 92, 463-466
    • (2013) Life Sci. , vol.92 , pp. 463-466
    • Van Dross, R.1    Soliman, E.2    Jha, S.3    Johnson, T.4    Mukhopadhyay, S.5
  • 9
    • 33746125474 scopus 로고    scopus 로고
    • Delta9-tetrahydrocannabinol inhibits cell cycle progression in human breast cancer cells through Cdc2 regulation
    • Caffarel, M. M.; Sarrió, D.; Palacios, J.; Guzmán, M.; Sánchez, C. Delta9-tetrahydrocannabinol inhibits cell cycle progression in human breast cancer cells through Cdc2 regulation Cancer Res. 2006, 66, 6615-6621
    • (2006) Cancer Res. , vol.66 , pp. 6615-6621
    • Caffarel, M.M.1    Sarrió, D.2    Palacios, J.3    Guzmán, M.4    Sánchez, C.5
  • 11
    • 79960115996 scopus 로고    scopus 로고
    • Cannabidiol induces programmed cell death in breast cancer cells by coordinating the cross-talk between apoptosis and autophagy
    • Shrivastava, A.; Kuzontkoski, P. M.; Groopman, J. E.; Prasad, A. Cannabidiol induces programmed cell death in breast cancer cells by coordinating the cross-talk between apoptosis and autophagy Mol. Cancer Ther. 2011, 10, 1161-1172
    • (2011) Mol. Cancer Ther. , vol.10 , pp. 1161-1172
    • Shrivastava, A.1    Kuzontkoski, P.M.2    Groopman, J.E.3    Prasad, A.4
  • 13
    • 33750507764 scopus 로고    scopus 로고
    • Anandamide inhibits Cdk2 and activates Chk1 leading to cell cycle arrest in human breast cancer cells
    • Laezza, C.; Pisanti, S.; Crescenzi, E.; Bifulco, M. Anandamide inhibits Cdk2 and activates Chk1 leading to cell cycle arrest in human breast cancer cells FEBS Lett. 2006, 580, 6076-6082
    • (2006) FEBS Lett. , vol.580 , pp. 6076-6082
    • Laezza, C.1    Pisanti, S.2    Crescenzi, E.3    Bifulco, M.4
  • 14
    • 70949091684 scopus 로고    scopus 로고
    • Synthetic cannabinoid receptor agonists inhibit tumor growth and metastasis of breast cancer
    • Qamri, Z.; Preet, A.; Nasser, M. W.; Bass, C. E.; Leone, G.; Barsky, S. H.; Ganju, R. K. Synthetic cannabinoid receptor agonists inhibit tumor growth and metastasis of breast cancer Mol. Cancer Ther. 2009, 8, 3117-3129
    • (2009) Mol. Cancer Ther. , vol.8 , pp. 3117-3129
    • Qamri, Z.1    Preet, A.2    Nasser, M.W.3    Bass, C.E.4    Leone, G.5    Barsky, S.H.6    Ganju, R.K.7
  • 16
    • 70249094588 scopus 로고    scopus 로고
    • Inhibition of human tumour prostate PC-3 cell growth by cannabinoids R(+)-methanandamide and JWH-015: Involvement of CB2
    • Olea-Herrero, N.; Vara, D.; Malagarie-Cazenave, S.; Diaz-Laviada, I. Inhibition of human tumour prostate PC-3 cell growth by cannabinoids R(+)-methanandamide and JWH-015: involvement of CB2 Br. J. Cancer 2009, 101, 940-950
    • (2009) Br. J. Cancer , vol.101 , pp. 940-950
    • Olea-Herrero, N.1    Vara, D.2    Malagarie-Cazenave, S.3    Diaz-Laviada, I.4
  • 17
    • 84887974190 scopus 로고    scopus 로고
    • Therapeutic utility of cannabinoid receptor type 2 (CB2) selective agonists
    • Han, S.; Thatte, J.; Buzard, D. J.; Jones, R. M. Therapeutic utility of cannabinoid receptor type 2 (CB2) selective agonists J. Med. Chem. 2013, 56, 8224-8256
    • (2013) J. Med. Chem. , vol.56 , pp. 8224-8256
    • Han, S.1    Thatte, J.2    Buzard, D.J.3    Jones, R.M.4
  • 20
    • 33845603466 scopus 로고    scopus 로고
    • Non-psychoactive CB2 cannabinoid agonists stimulate neural progenitor proliferation
    • Palazuelos, J.; Aguado, T.; Egia, A.; Mechoulam, R.; Guzmán, M.; Galve-Roperh, I. Non-psychoactive CB2 cannabinoid agonists stimulate neural progenitor proliferation FASEB J. 2006, 20, 2405-2407
    • (2006) FASEB J. , vol.20 , pp. 2405-2407
    • Palazuelos, J.1    Aguado, T.2    Egia, A.3    Mechoulam, R.4    Guzmán, M.5    Galve-Roperh, I.6
  • 21
    • 84868128338 scopus 로고    scopus 로고
    • Targeting the endocannabinoid system with cannabinoid receptor agonists: Pharmacological strategies and therapeutic possibilities
    • Pertwee, R. G. Targeting the endocannabinoid system with cannabinoid receptor agonists: pharmacological strategies and therapeutic possibilities Philos. Trans. R. Soc., B 2012, 367, 3353-3363
    • (2012) Philos. Trans. R. Soc., B , vol.367 , pp. 3353-3363
    • Pertwee, R.G.1
  • 22
    • 84887184189 scopus 로고    scopus 로고
    • Another review on triple negative breast cancer. Are we on the right way towards the exit from the labyrinth?
    • Chiorean, R.; Braicu, C.; Berindan-Neagoe, I. Another review on triple negative breast cancer. Are we on the right way towards the exit from the labyrinth? Breast 2013, 22, 1026-1033
    • (2013) Breast , vol.22 , pp. 1026-1033
    • Chiorean, R.1    Braicu, C.2    Berindan-Neagoe, I.3
  • 23
    • 84919327274 scopus 로고    scopus 로고
    • Subtyping of triple-negative breast cancer: Implications for therapy
    • Abramson, V. G.; Lehmann, B. D.; Ballinger, T. J.; Pietenpol, J. A. Subtyping of triple-negative breast cancer: implications for therapy Cancer 2014, 1-9
    • (2014) Cancer , pp. 1-9
    • Abramson, V.G.1    Lehmann, B.D.2    Ballinger, T.J.3    Pietenpol, J.A.4
  • 24
    • 84924676135 scopus 로고    scopus 로고
    • Challenges in the treatment of triple negative and HER2-overexpressing breast cancer
    • Hoeferlin, L. A.; E.Chalfant, C. E.; Park, M. A. Challenges in the treatment of triple negative and HER2-overexpressing breast cancer J. Surg. Sci. 2013, 1, 3-7
    • (2013) J. Surg. Sci. , vol.1 , pp. 3-7
    • Hoeferlin, L.A.1    Chalfant, C.E.E.2    Park, M.A.3
  • 26
    • 79959503213 scopus 로고    scopus 로고
    • Triple-negative breast cancer: An unmet medical need
    • Hudis, C. A.; Gianni, L. Triple-negative breast cancer: an unmet medical need Oncologist 2011, 16, 1-11
    • (2011) Oncologist , vol.16 , pp. 1-11
    • Hudis, C.A.1    Gianni, L.2
  • 27
    • 84884539933 scopus 로고    scopus 로고
    • Triple-negative breast cancer and the need for new therapeutic targets
    • Engebraaten, O.; Vollan, H. K. M.; Børresen-Dale, A.-L. Triple-negative breast cancer and the need for new therapeutic targets Am. J. Pathol. 2013, 183, 1064-1074
    • (2013) Am. J. Pathol. , vol.183 , pp. 1064-1074
    • Engebraaten, O.1    Vollan, H.K.M.2    Børresen-Dale, A.-L.3
  • 31
    • 76749109850 scopus 로고    scopus 로고
    • Regiospecific oxidation of polycyclic aromatic phenols to quinones by hypervalent iodine reagents
    • Wu, A.; Duan, Y.; Xu, D.; Penning, T. M.; Harvey, R. G. Regiospecific oxidation of polycyclic aromatic phenols to quinones by hypervalent iodine reagents Tetrahedron 2010, 66, 2111-2118
    • (2010) Tetrahedron , vol.66 , pp. 2111-2118
    • Wu, A.1    Duan, Y.2    Xu, D.3    Penning, T.M.4    Harvey, R.G.5
  • 32
    • 0037165401 scopus 로고    scopus 로고
    • Regioselective oxidation of phenols to o-quinones with o-iodoxybenzoic acid (IBX)
    • Magdziak, D.; Rodriguez, A. A.; Van De Water, R. W.; Pettus, T. R. R. Regioselective oxidation of phenols to o-quinones with o-iodoxybenzoic acid (IBX) Org. Lett. 2002, 285-288
    • (2002) Org. Lett. , pp. 285-288
    • Magdziak, D.1    Rodriguez, A.A.2    Van De Water, R.W.3    Pettus, T.R.R.4
  • 33
    • 1642272391 scopus 로고    scopus 로고
    • Synthesis of the o-quinones and other oxidized metabolites of polycyclic aromatic hydrocarbons implicated in carcinogenesis
    • Harvey, R. G.; Dai, Q.; Ran, C.; Penning, T. M. Synthesis of the o-quinones and other oxidized metabolites of polycyclic aromatic hydrocarbons implicated in carcinogenesis J. Org. Chem. 2004, 69, 2024-2032
    • (2004) J. Org. Chem. , vol.69 , pp. 2024-2032
    • Harvey, R.G.1    Dai, Q.2    Ran, C.3    Penning, T.M.4
  • 34
    • 77955418560 scopus 로고    scopus 로고
    • Selective and efficient oxidative modifications of flavonoids with 2-iodoxybenzoic acid (IBX)
    • Barontini, M.; Bernini, R.; Crisante, F.; Fabrizi, G. Selective and efficient oxidative modifications of flavonoids with 2-iodoxybenzoic acid (IBX) Tetrahedron 2010, 66, 6047-6053
    • (2010) Tetrahedron , vol.66 , pp. 6047-6053
    • Barontini, M.1    Bernini, R.2    Crisante, F.3    Fabrizi, G.4
  • 36
    • 0037364162 scopus 로고    scopus 로고
    • ADMET in silico modelling: Towards prediction paradise?
    • Van de Waterbeemd, H.; Gifford, E. ADMET in silico modelling: towards prediction paradise? Nat. Rev. Drug Discovery 2003, 2, 192-204
    • (2003) Nat. Rev. Drug Discovery , vol.2 , pp. 192-204
    • Van De Waterbeemd, H.1    Gifford, E.2
  • 37
    • 0037204544 scopus 로고    scopus 로고
    • Prediction of drug solubility from structure
    • Jorgensen, W. L.; Duffy, E. M. Prediction of drug solubility from structure Adv. Drug Delivery Rev. 2002, 54, 355-366
    • (2002) Adv. Drug Delivery Rev. , vol.54 , pp. 355-366
    • Jorgensen, W.L.1    Duffy, E.M.2
  • 38
    • 0034461768 scopus 로고    scopus 로고
    • Drug-like properties and the causes of poor solubility and poor permeability
    • Lipinski, C. A. Drug-like properties and the causes of poor solubility and poor permeability J. Pharmacol. Toxicol. Methods 2001, 44, 235-249
    • (2001) J. Pharmacol. Toxicol. Methods , vol.44 , pp. 235-249
    • Lipinski, C.A.1
  • 41
    • 84891836326 scopus 로고    scopus 로고
    • Systematic review of the literature on clinical and experimental trials on the antitumor effects of cannabinoids in gliomas
    • Rocha, F. C. M.; Dos Santos Júnior, J. G.; Stefano, S. C.; da Silveira, D. X. Systematic review of the literature on clinical and experimental trials on the antitumor effects of cannabinoids in gliomas J. Neurooncol. 2014, 116, 11-24
    • (2014) J. Neurooncol. , vol.116 , pp. 11-24
    • Rocha, F.C.M.1    Dos Santos Júnior, J.G.2    Stefano, S.C.3    Da Silveira, D.X.4
  • 43
    • 84907943686 scopus 로고    scopus 로고
    • Polypharmacology: Challenges and opportunities in drug discovery
    • Anighoro, A.; Bajorath, J.; Rastelli, G. Polypharmacology: challenges and opportunities in drug discovery J. Med. Chem. 2014, 57, 7874-7887
    • (2014) J. Med. Chem. , vol.57 , pp. 7874-7887
    • Anighoro, A.1    Bajorath, J.2    Rastelli, G.3
  • 44
    • 72949087797 scopus 로고    scopus 로고
    • Promise and challenges in drug discovery and development of hybrid anticancer drugs
    • Gediya, L. K.; Njar, V. C. O. Promise and challenges in drug discovery and development of hybrid anticancer drugs Expert Opin. Drug Discovery 2009, 4, 1099-1111
    • (2009) Expert Opin. Drug Discovery , vol.4 , pp. 1099-1111
    • Gediya, L.K.1    Njar, V.C.O.2
  • 46
    • 84889575198 scopus 로고    scopus 로고
    • Modulation of oxidative stress as an anticancer strategy
    • Gorrini, C.; Harris, I. S.; Mak, T. W. Modulation of oxidative stress as an anticancer strategy Nat. Rev. Drug Discovery 2013, 12, 931-947
    • (2013) Nat. Rev. Drug Discovery , vol.12 , pp. 931-947
    • Gorrini, C.1    Harris, I.S.2    Mak, T.W.3
  • 47
    • 61349143694 scopus 로고    scopus 로고
    • The enigmatic pharmacology of GPR55
    • Ross, R. A. The enigmatic pharmacology of GPR55 Trends Pharmacol. Sci. 2009, 30, 156-163
    • (2009) Trends Pharmacol. Sci. , vol.30 , pp. 156-163
    • Ross, R.A.1
  • 48
    • 36448995830 scopus 로고    scopus 로고
    • GPR55: A new member of the cannabinoid receptor clan?
    • Pertwee, R. G. GPR55: a new member of the cannabinoid receptor clan? Br. J. Pharmacol. 2007, 152, 984-986
    • (2007) Br. J. Pharmacol. , vol.152 , pp. 984-986
    • Pertwee, R.G.1
  • 49
    • 77952627758 scopus 로고    scopus 로고
    • A role for L-α-lysophosphatidylinositol and GPR55 in the modulation of migration, orientation and polarization of human breast cancer cells
    • Ford, L. A.; Roelofs, A. J.; Anavi-Goffer, S.; Mowat, L.; Simpson, D. G.; Irving, A. J.; Rogers, M. J.; Rajnicek, A. M.; Ross, R. A. A role for L-α-lysophosphatidylinositol and GPR55 in the modulation of migration, orientation and polarization of human breast cancer cells Br. J. Pharmacol. 2010, 160, 762-771
    • (2010) Br. J. Pharmacol. , vol.160 , pp. 762-771
    • Ford, L.A.1    Roelofs, A.J.2    Anavi-Goffer, S.3    Mowat, L.4    Simpson, D.G.5    Irving, A.J.6    Rogers, M.J.7    Rajnicek, A.M.8    Ross, R.A.9
  • 50
    • 0027138551 scopus 로고
    • Radioligand binding methods-practical guide and tips
    • Bylund, D.; Toews, M. Radioligand binding methods-practical guide and tips Am. J. Physiol. 1993, 265, L421-L429
    • (1993) Am. J. Physiol. , vol.265 , pp. 421-L429
    • Bylund, D.1    Toews, M.2


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