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Volumn 70, Issue , 2013, Pages 111-119

Synthetic cannabinoid quinones: Preparation, in vitro antiproliferative effects and in vivo prostate antitumor activity

Author keywords

Antiproliferative; Antitumor; Cannabinoid; Chromenopyrazoledione; Electrochemistry; Prostate cancer; Quinone

Indexed keywords

2 CHLORO 5 NITROBENZANILIDE; 5 (4 CHLORO 3 METHYLPHENYL) 1 (4 METHYLBENZYL) N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 3 PYRAZOLECARBOXAMIDE; 7 (1',1' DIMETHYLHEPTYL) 1,4 DIHYDRO 4,4 DIMETHYLCHROMENO [4,3 C]PYRAZOL 6,9 DIONE; 7 (1',1' DIMETHYLHEPTYL) 2 ETHYL 2,4 DIHYDRO 4,4 DIMETHYLCHROMENO [4,3 C]PYRAZOL 6,9 DIONE; 7 (1',1' DIMETHYLHEPTYL) 2,4 DIHYDRO 2,4,4 TRIMETHYLCHROMENO [4,3 C]PYRAZOL 6,9 DIONE; ACETYLCYSTEINE; ANTINEOPLASTIC AGENT; CANNABINOID 1 RECEPTOR; CANNABINOID 2 RECEPTOR; CANNABINOID DERIVATIVE; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA; QUINONE DERIVATIVE; REACTIVE OXYGEN METABOLITE; RIMONABANT; UNCLASSIFIED DRUG;

EID: 84885500963     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.09.043     Document Type: Article
Times cited : (39)

References (33)
  • 2
    • 83455246740 scopus 로고    scopus 로고
    • Progress of molecular targeted therapies for prostate cancers
    • W.H. Fu, E. Madan, M. Yee, and H.T. Zhang Progress of molecular targeted therapies for prostate cancers BBA Rev. Cancer 1825 2012 140 152
    • (2012) BBA Rev. Cancer , vol.1825 , pp. 140-152
    • Fu, W.H.1    Madan, E.2    Yee, M.3    Zhang, H.T.4
  • 3
    • 80054868596 scopus 로고    scopus 로고
    • Designed multiple ligands for cancer therapy
    • N.M. O'Boyle, and M.J. Meegan Designed multiple ligands for cancer therapy Curr. Med. Chem. 18 2011 4722 4737
    • (2011) Curr. Med. Chem. , vol.18 , pp. 4722-4737
    • O'Boyle, N.M.1    Meegan, M.J.2
  • 4
    • 72949087797 scopus 로고    scopus 로고
    • Promise and challenges in drug discovery and development of hybrid anticancer drugs
    • L.K. Gediya, and V.C.O. Njar Promise and challenges in drug discovery and development of hybrid anticancer drugs Expert Opin. Drug Discovery 4 2009 1099 1111
    • (2009) Expert Opin. Drug Discovery , vol.4 , pp. 1099-1111
    • Gediya, L.K.1    Njar, V.C.O.2
  • 5
    • 65449146377 scopus 로고    scopus 로고
    • Emerging strategies for exploiting cannabinoid receptor agonists as medicines
    • R.G. Pertwee Emerging strategies for exploiting cannabinoid receptor agonists as medicines Br. J. Pharmacol. 156 2009 397 411
    • (2009) Br. J. Pharmacol. , vol.156 , pp. 397-411
    • Pertwee, R.G.1
  • 6
    • 84861530762 scopus 로고    scopus 로고
    • Towards the use of cannabinoids as antitumour agents
    • G. Velasco, C. Sanchez, and M. Guzman Towards the use of cannabinoids as antitumour agents Nat. Rev. Cancer 12 2012 436 444
    • (2012) Nat. Rev. Cancer , vol.12 , pp. 436-444
    • Velasco, G.1    Sanchez, C.2    Guzman, M.3
  • 7
    • 0142166330 scopus 로고    scopus 로고
    • Cannabinoids: Potential anticancer agents
    • M. Guzman Cannabinoids: potential anticancer agents Nat. Rev. Cancer 3 2003 745 755 (Pubitemid 37328813)
    • (2003) Nature Reviews Cancer , vol.3 , Issue.10 , pp. 745-755
    • Guzman, M.1
  • 8
    • 39049104489 scopus 로고    scopus 로고
    • Cannabinoids for cancer treatment: Progress and promise
    • DOI 10.1158/0008-5472.CAN-07-2785
    • S. Sarfaraz, V.M. Adhami, D.N. Syed, F. Afaq, and H. Mukhtar Cannabinoids for cancer treatment: progress and promise Cancer Res. 68 2008 339 342 (Pubitemid 351380057)
    • (2008) Cancer Research , vol.68 , Issue.2 , pp. 339-342
    • Sarfaraz, S.1    Adhami, V.M.2    Syed, D.N.3    Afaq, F.4    Mukhtar, H.5
  • 10
    • 79955692485 scopus 로고    scopus 로고
    • The endocannabinoid system in the cancer therapy: An overview
    • C. Grimaldi, and A. Capasso The endocannabinoid system in the cancer therapy: an overview Curr. Med. Chem. 18 2011 1575 1583
    • (2011) Curr. Med. Chem. , vol.18 , pp. 1575-1583
    • Grimaldi, C.1    Capasso, A.2
  • 14
    • 80054021457 scopus 로고    scopus 로고
    • The endocannabinoid system in prostate cancer
    • I. Diaz-Laviada The endocannabinoid system in prostate cancer Nat. Rev. Urol. 8 2011 553 561
    • (2011) Nat. Rev. Urol. , vol.8 , pp. 553-561
    • Diaz-Laviada, I.1
  • 16
    • 77956278506 scopus 로고    scopus 로고
    • Cannabinoid receptor-dependent and -independent anti-proliferative effects of omega-3 ethanolamides in androgen receptor-positive and -negative prostate cancer cell lines
    • I. Brown, M.G. Cascio, K.W.J. Wahle, R. Smoum, R. Mechoulam, R.A. Ross, R.G. Pertwee, and S.D. Heys Cannabinoid receptor-dependent and -independent anti-proliferative effects of omega-3 ethanolamides in androgen receptor-positive and -negative prostate cancer cell lines Carcinogenesis 31 2010 1584 1591
    • (2010) Carcinogenesis , vol.31 , pp. 1584-1591
    • Brown, I.1    Cascio, M.G.2    Wahle, K.W.J.3    Smoum, R.4    Mechoulam, R.5    Ross, R.A.6    Pertwee, R.G.7    Heys, S.D.8
  • 17
    • 18044375989 scopus 로고    scopus 로고
    • Antitumour quinones
    • DOI 10.2174/1389557053765556
    • C. Asche Antitumour quinones Mini Rev. Med. Chem. 5 2005 449 467 (Pubitemid 40601636)
    • (2005) Mini-Reviews in Medicinal Chemistry , vol.5 , Issue.5 , pp. 449-467
    • Asche, C.1
  • 21
    • 0042416813 scopus 로고    scopus 로고
    • Recent progress in the synthesis of p-quinones and p-dihydroquinones through oxidation of phenol derivatives. A review
    • S. Akai, and Y. Kita Recent progress in the synthesis of p-quinones and p-dihydro-quinones through oxidation of phenol derivative. A review Org. Prep. Proced. Int. 30 1998 603 629 (Pubitemid 128385889)
    • (1998) Organic Preparations and Procedures International , vol.30 , Issue.6 , pp. 603-629
    • Akai, S.1    Kita, Y.2
  • 22
    • 0025181162 scopus 로고
    • Oxidation of phenols to quinones by bis(trifluoroacetoxy)iodobenzene
    • DOI 10.1016/S0040-4039(00)97755-4
    • R. Barret, and M. Daudon Oxidation of phenols to quinones by bis(trifluoroacetoxy)iodobenzene Tetrahedron Lett. 31 1990 4871 4872 (Pubitemid 20251231)
    • (1990) Tetrahedron Letters , vol.31 , Issue.34 , pp. 4871-4872
    • Barret, R.1    Daudon, M.2
  • 23
    • 57749188229 scopus 로고    scopus 로고
    • Capsaicin, a component of red peppers, induces expression of androgen receptor via PI3K and MAPK pathways in prostate LNCaP cells
    • S. Malagarie-Cazenave, N. Olea-Herrero, D. Vara, and I. Diaz-Laviada Capsaicin, a component of red peppers, induces expression of androgen receptor via PI3K and MAPK pathways in prostate LNCaP cells FEBS Lett. 583 2009 141 147
    • (2009) FEBS Lett. , vol.583 , pp. 141-147
    • Malagarie-Cazenave, S.1    Olea-Herrero, N.2    Vara, D.3    Diaz-Laviada, I.4
  • 24
    • 16444375370 scopus 로고    scopus 로고
    • Cannabinoid receptor as a novel target for the treatment of prostate cancer
    • DOI 10.1158/0008-5472.CAN-04-3410
    • S. Sarfaraz, F. Afaq, V.M. Adhami, and H. Mukhtar Cannabinoid receptor as a novel target for the treatment of prostate cancer Cancer Res. 65 2005 1635 1641 (Pubitemid 40478586)
    • (2005) Cancer Research , vol.65 , Issue.5 , pp. 1635-1641
    • Sarfaraz, S.1    Afaq, F.2    Adhami, V.M.3    Mukhtar, H.4
  • 25
    • 84886295676 scopus 로고    scopus 로고
    • Management of biochemical recurrence after primary localized therapy for prostate cancer
    • O.M. Darwish, and G.V. Raj Management of biochemical recurrence after primary localized therapy for prostate cancer Front. Oncol. 2 2012 48
    • (2012) Front. Oncol. , vol.2 , pp. 48
    • Darwish, O.M.1    Raj, G.V.2
  • 26
    • 79851492750 scopus 로고    scopus 로고
    • Androgen deprivation therapy in men with prostate cancer: How should the side effects be monitored and treated?
    • M. Grossmann, and J.D. Zajac Androgen deprivation therapy in men with prostate cancer: how should the side effects be monitored and treated? Clin. Endocrinol. 74 2011 289 293
    • (2011) Clin. Endocrinol. , vol.74 , pp. 289-293
    • Grossmann, M.1    Zajac, J.D.2
  • 27
    • 79959789098 scopus 로고    scopus 로고
    • Plastoquinones from Sargassum yezoense; Chemical structures and effects on the activation of peroxisome proliferator-activated receptor gamma
    • M.C. Kim, H.C. Kwon, S.N. Kim, H.S. Kim, and B.H. Um Plastoquinones from Sargassum yezoense; chemical structures and effects on the activation of peroxisome proliferator-activated receptor gamma Chem. Pharm. Bull. 59 2011 834 838
    • (2011) Chem. Pharm. Bull. , vol.59 , pp. 834-838
    • Kim, M.C.1    Kwon, H.C.2    Kim, S.N.3    Kim, H.S.4    Um, B.H.5
  • 28
    • 75849147916 scopus 로고    scopus 로고
    • Anti-diabetic effects of emodin involved in the activation of PPAR gamma on high-fat diet-fed and low dose of streptozotocin-induced diabetic mice
    • J. Xue, W. Ding, and Y. Liu Anti-diabetic effects of emodin involved in the activation of PPAR gamma on high-fat diet-fed and low dose of streptozotocin-induced diabetic mice Fitoterapia 81 2010 173 177
    • (2010) Fitoterapia , vol.81 , pp. 173-177
    • Xue, J.1    Ding, W.2    Liu, Y.3
  • 29
    • 79960929095 scopus 로고    scopus 로고
    • Anticancer activity of thymoquinone in breast cancer cells: Possible involvement of PPAR-gamma pathway
    • C.C. Woo, S.Y. Loo, V. Gee, C.W. Yap, G. Sethi, A.P. Kumar, and K.H. Tan Anticancer activity of thymoquinone in breast cancer cells: possible involvement of PPAR-gamma pathway Biochem. Pharmacol. 82 2011 464 475
    • (2011) Biochem. Pharmacol. , vol.82 , pp. 464-475
    • Woo, C.C.1    Loo, S.Y.2    Gee, V.3    Yap, C.W.4    Sethi, G.5    Kumar, A.P.6    Tan, K.H.7
  • 30
    • 84871610611 scopus 로고    scopus 로고
    • Ardisianone, a natural benzoquinone, efficiently induces apoptosis in human hormone-refractory prostate cancers through mitochondrial damage stress and survivin downregulation
    • C.C. Yu, P.J. Wu, J.L. Hsu, Y.F. Ho, L.C. Hsu, Y.J. Chang, H.S. Chang, I.S. Chen, and J.H. Guh Ardisianone, a natural benzoquinone, efficiently induces apoptosis in human hormone-refractory prostate cancers through mitochondrial damage stress and survivin downregulation Prostate 73 2013 133 145
    • (2013) Prostate , vol.73 , pp. 133-145
    • Yu, C.C.1    Wu, P.J.2    Hsu, J.L.3    Ho, Y.F.4    Hsu, L.C.5    Chang, Y.J.6    Chang, H.S.7    Chen, I.S.8    Guh, J.H.9
  • 31
    • 84855780132 scopus 로고    scopus 로고
    • Synthesis, antiproliferative activities and telomerase inhibition evaluation of novel asymmetrical 1,2-disubstituted amidoanthraquinone derivatives
    • C.C. Lee, K.F. Huang, P.Y. Lin, F.C. Huang, C.L. Chen, T.C. Chen, J.H. Guh, J.J. Lin, and H.S. Huang Synthesis, antiproliferative activities and telomerase inhibition evaluation of novel asymmetrical 1,2-disubstituted amidoanthraquinone derivatives Eur. J. Med. Chem. 47 2012 323 336
    • (2012) Eur. J. Med. Chem. , vol.47 , pp. 323-336
    • Lee, C.C.1    Huang, K.F.2    Lin, P.Y.3    Huang, F.C.4    Chen, C.L.5    Chen, T.C.6    Guh, J.H.7    Lin, J.J.8    Huang, H.S.9
  • 32
    • 80052306051 scopus 로고    scopus 로고
    • Synthesis and antiproliferative activity of 1,4-bis(dimethylamino)-9,10- anthraquinone derivatives against P388 mouse leukemic tumor cells
    • G.Z. Jin, H.S. Jin, and L.L. Jin Synthesis and antiproliferative activity of 1,4-bis(dimethylamino)-9,10-anthraquinone derivatives against P388 mouse leukemic tumor cells Arch. Pharm. Res. 34 2011 1071 1076
    • (2011) Arch. Pharm. Res. , vol.34 , pp. 1071-1076
    • Jin, G.Z.1    Jin, H.S.2    Jin, L.L.3
  • 33
    • 81755188279 scopus 로고    scopus 로고
    • The chemical biology of naphthoquinones and its environmental implications
    • Y. Kumagai, Y. Shinkai, T. Miura, A.K. Cho, The chemical biology of naphthoquinones and its environmental implications, Annu. Rev. Pharmacol. 52 (2012) 221-247.
    • (2012) Annu. Rev. Pharmacol. , vol.52 , pp. 221-247
    • Kumagai, Y.1    Shinkai, Y.2    Miura, T.3    Cho, A.K.4


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