메뉴 건너뛰기




Volumn 15, Issue 11, 2015, Pages 1035-1042

(6-Bromo-1,4-dimethyl-9H-carbazol-3-yl-methylene)-hydrazine (Carbhydraz) acts as a GPER Agonist in Breast Cancer Cells

Author keywords

Breast cancer; Carbazole derivatives; Docking simulations; Estrogen estrogen receptors; GPR30 GPER; Heterocycle

Indexed keywords

(6 BROMO 1,4 DIMETHYL 9H CARBAZOL 3 YL METHYLENE) HYDRAZINE; (6 METHOXY 1,4 DIMETHYL 9H CARBAZOL 3 YL METHYLENE) HYDRAZINE; 6 BROMO 1,4 DIMETHYL 9H CARBAZOL 3 YL METHYLENE HYDRAZINE CARBHYDRAZ; ANTINEOPLASTIC AGENT; ESTROGEN; ESTROGEN RECEPTOR; G PROTEIN COUPLED RECEPTOR 30; MITOGEN ACTIVATED PROTEIN KINASE 1; MITOGEN ACTIVATED PROTEIN KINASE 3; N,N BIS (6 BROMO 1,4 DIMETHYL 9H CARBAZOL 3 YLMETHYLENE) HYDRAZINE; N,N BIS 6 BROMO 1,4 DIMETHYL 9H CARBAZOL 3 YL METHYLENE HYDRAZINE; UNCLASSIFIED DRUG; (6-BROMO-1,4-DIMETHYL-9H-CARBAZOL-3-YLMETHYLENE)HYDRAZINE; CARBAZOLE DERIVATIVE; G PROTEIN COUPLED RECEPTOR; GPER PROTEIN, HUMAN; HYDRAZINE DERIVATIVE; MAPK1 PROTEIN, HUMAN;

EID: 84928893208     PISSN: 15680266     EISSN: 18734294     Source Type: Journal    
DOI: 10.2174/1568026615666150317221549     Document Type: Article
Times cited : (30)

References (58)
  • 1
    • 63149092203 scopus 로고    scopus 로고
    • Alkaloids as potential anti-tubercular agents
    • Kishore, N.; Mishra, B.B.; Tripathi, V.; Tiwari, V.K. Alkaloids as potential anti-tubercular agents. Fitoterapia, 2009, 80(3), 149-163.
    • (2009) Fitoterapia , vol.80 , Issue.3 , pp. 149-163
    • Kishore, N.1    Mishra, B.B.2    Tripathi, V.3    Tiwari, V.K.4
  • 2
    • 33751522598 scopus 로고    scopus 로고
    • Synthesis of Carbazoles and Dibenzofurans via Cross-Coupling of o-Iodoanilines and o-Iodophenols with Silylaryl Triflates and Subsequent Pd-Catalyzed Cyclization
    • Liu, Z.; Larock, R.C. Synthesis of Carbazoles and Dibenzofurans via Cross-Coupling of o-Iodoanilines and o-Iodophenols with Silylaryl Triflates and Subsequent Pd-Catalyzed Cyclization. Tetrahedron, 2007, 63(2), 347-355.
    • (2007) Tetrahedron , vol.63 , Issue.2 , pp. 347-355
    • Liu, Z.1    Larock, R.C.2
  • 5
    • 37349045723 scopus 로고    scopus 로고
    • Novel and efficient synthesis of 5,8- dimethyl-9H-carbazol-3-ol via a hydroxydeboronation reaction
    • Caruso, A.; Voisin-Chiret, A.S.; Lancelot, J.C.; Sinicropi, M.S.; Garofalo, A.; Rault, S. Novel and efficient synthesis of 5,8- dimethyl-9H-carbazol-3-ol via a hydroxydeboronation reaction. Heterocycles, 2007, 71(10), 2203-2210.
    • (2007) Heterocycles , vol.71 , Issue.10 , pp. 2203-2210
    • Caruso, A.1    Voisin-Chiret, A.S.2    Lancelot, J.C.3    Sinicropi, M.S.4    Garofalo, A.5    Rault, S.6
  • 9
    • 0343596324 scopus 로고
    • Efficient synthesis of 6-substituted 3-nitro-1,4- dimethylcarbazoles and 3-amino-1,4-dimethylcarbazoles
    • Lancelot, J.C.; Letois, B.; Rault, S.; Dung, N.H.; Saturnino, C.; Robba M. Efficient synthesis of 6-substituted 3-nitro-1,4- dimethylcarbazoles and 3-amino-1,4-dimethylcarbazoles. Gazz. Chim. Ital., 1991, 121, 301-307.
    • (1991) Gazz. Chim. Ital , vol.121 , pp. 301-307
    • Lancelot, J.C.1    Letois, B.2    Rault, S.3    Dung, N.H.4    Saturnino, C.5    Robba, M.6
  • 12
    • 2142771242 scopus 로고    scopus 로고
    • Synthesis and preliminary biological evaluation of a new pyridocarbazole derivative covalently linked to a thymidine nucleoside as a potential targeted antitumoral agent
    • Saturnino, C.; Buonerba, M.; Boatto, G.; Pascale, M.; Moltedo, O.; De Napoli, L.; Montesarchio, D.; Lancelot, J.C.; De Caprariis, P. Synthesis and preliminary biological evaluation of a new pyridocarbazole derivative covalently linked to a thymidine nucleoside as a potential targeted antitumoral agent. Chem. Pharm. Bull., 2003, 51, 971-974.
    • (2003) Chem. Pharm. Bull , vol.51 , pp. 971-974
    • Saturnino, C.1    Buonerba, M.2    Boatto, G.3    Pascale, M.4    Moltedo, O.5    De Napoli, L.6    Montesarchio, D.7    Lancelot, J.C.8    De Caprariis, P.9
  • 16
    • 85039877516 scopus 로고
    • Benzo[a]carbazole derivatives. Synthesis, estrogen receptor binding affinities and mammary tumor inhibiting activity
    • von Angerer, E.; Prekajac, J. Benzo[a]carbazole derivatives. Synthesis, estrogen receptor binding affinities and mammary tumor inhibiting activity. J. Med. Chem., 1986, 26, 113-116.
    • (1986) J. Med. Chem , vol.26 , pp. 113-116
    • Von Angerer, E.1    Prekajac, J.2
  • 17
    • 33747466839 scopus 로고    scopus 로고
    • Structurefunction relationship of estrogen receptor a and b:Impact on human health
    • Ascenzi, P.; Bocedi, A.; Marino, M. Structurefunction relationship of estrogen receptor a and b:impact on human health. Mol. Aspects Med., 2006, 27, 299-402.
    • (2006) Mol. Aspects Med , vol.27 , pp. 299-402
    • Ascenzi, P.1    Bocedi, A.2    Marino, M.3
  • 18
    • 82155173499 scopus 로고    scopus 로고
    • The G-protein-coupled estrogen receptor GPER in health and disease
    • Prossnitz, E.R.; Barton, M. The G-protein-coupled estrogen receptor GPER in health and disease. Nat. Rev. Endocrinol., 2011, 7, 715-26.
    • (2011) Nat. Rev. Endocrinol , vol.7 , pp. 715-726
    • Prossnitz, E.R.1    Barton, M.2
  • 19
    • 75149186664 scopus 로고    scopus 로고
    • The unfolding stories of GPR30, a new membrane bound estrogen receptor
    • Maggiolini, M., Picard, D. The unfolding stories of GPR30, a new membrane bound estrogen receptor. J. Endocrinol., 2010, 204, 105-114.
    • (2010) J. Endocrinol , vol.204 , pp. 105-114
    • Maggiolini, M.1    Picard, D.2
  • 20
    • 12344307170 scopus 로고    scopus 로고
    • Identity of an estrogen membrane receptor coupled to a G protein in human breast cancer cells
    • Thomas, P.; Pang, Y.; Filardo, E.J.; Dong, J. Identity of an estrogen membrane receptor coupled to a G protein in human breast cancer cells. Endocrinology, 2005, 146, 624-632.
    • (2005) Endocrinology , vol.146 , pp. 624-632
    • Thomas, P.1    Pang, Y.2    Filardo, E.J.3    Dong, J.4
  • 21
    • 14844343093 scopus 로고    scopus 로고
    • A transmembrane intracellular estrogen receptor mediates rapid cell signaling
    • Revankar, C.M.; Cimino, D.F.; Sklar, L.A.; Arterburn, J.B.; Prossnitz, E.R. A transmembrane intracellular estrogen receptor mediates rapid cell signaling. Science, 2005, 307, 1625-1630
    • (2005) Science , vol.307 , pp. 1625-1630
    • Revankar, C.M.1    Cimino, D.F.2    Sklar, L.A.3    Arterburn, J.B.4    Prossnitz, E.R.5
  • 22
    • 33750992478 scopus 로고    scopus 로고
    • Binding and activation of the seventransmembrane estrogen receptor GPR30 by environmental estrogens: A potential novel mechanism of endocrine disruption
    • Thomas, P.; Dong, J. Binding and activation of the seventransmembrane estrogen receptor GPR30 by environmental estrogens: a potential novel mechanism of endocrine disruption. J. Steroid Biochem. Mol. Biol., 2006, 102, 175-179.
    • (2006) J. Steroid Biochem. Mol. Biol , vol.102 , pp. 175-179
    • Thomas, P.1    Dong, J.2
  • 29
    • 0028922586 scopus 로고    scopus 로고
    • Ligplot. A program to generate schematic diagrams of protein-ligand interactions
    • Wallace, A.C.; Laskowski, R.A.; Thornton, J.N. Ligplot. A program to generate schematic diagrams of protein-ligand interactions. Protein Eng., 1996, 8, 127-134.
    • (1996) Protein Eng , vol.8 , pp. 127-134
    • Wallace, A.C.1    Laskowski, R.A.2    Thornton, J.N.3
  • 31
    • 79551647461 scopus 로고    scopus 로고
    • The cholesterol metabolite 25-hydroxycholesterol activates estrogen receptor a-mediated signaling in cancer cells and in cardiomyocytes
    • Lappano, R.; Recchia, A.G.; De Francesco, E.M.; Angelone, T.; Cerra, M.C.; Picard, D.; Maggiolini, M. The cholesterol metabolite 25-hydroxycholesterol activates estrogen receptor a-mediated signaling in cancer cells and in cardiomyocytes. PLoS One, 2011, 6-e16631.
    • (2011) Plos One , pp. e6-e16631
    • Lappano, R.1    Recchia, A.G.2    De Francesco, E.M.3    Angelone, T.4    Cerra, M.C.5    Picard, D.6    Maggiolini, M.7
  • 32
    • 62049084027 scopus 로고    scopus 로고
    • Estrogenic GPR30 signalling induces proliferation and migration of breast cancer cells through CTGF
    • Pandey, D.P.; Lappano, R.; Albanito, L.; Madeo, A.; Maggiolini, M.; Picard, D. Estrogenic GPR30 signalling induces proliferation and migration of breast cancer cells through CTGF. EMBO J., 2009, 28, 523-532.
    • (2009) EMBO J , vol.28 , pp. 523-532
    • Pandey, D.P.1    Lappano, R.2    Albanito, L.3    Madeo, A.4    Maggiolini, M.5    Picard, D.6
  • 35
    • 84927745951 scopus 로고
    • Chemischen Institut der Universität Jena: Methode zum Ersatz des Sauerstoffatoms der Ketone und Aldehyde durch Wasserstoff
    • Wolff, L. Chemischen Institut der Universität Jena: Methode zum Ersatz des Sauerstoffatoms der Ketone und Aldehyde durch Wasserstoff. Justus Liebigs Ann. Chem., 1912, 394(1), 86-108.
    • (1912) Justus Liebigs Ann. Chem , vol.394 , Issue.1 , pp. 86-108
    • Wolff, L.1
  • 36
    • 84864755972 scopus 로고    scopus 로고
    • Bisphenol A induces gene expression changes and proliferative effects through GPER in breast cancer cells and cancer-associated fibroblasts. Environ
    • Pupo, M.; Pisano, A.; Lappano, R.; Santolla, M.F.; De Francesco, E.F.; Rosano, C.; Maggiolini, M. Bisphenol A induces gene expression changes and proliferative effects through GPER in breast cancer cells and cancer-associated fibroblasts. Environ. Health Perspect., 2012, 120(8), 1177-1182.
    • (2012) Health Perspect , vol.120 , Issue.8 , pp. 1177-1182
    • Pupo, M.1    Pisano, A.2    Lappano, R.3    Santolla, M.F.4    De Francesco, E.F.5    Rosano, C.6    Maggiolini, M.7
  • 40
    • 33847755409 scopus 로고    scopus 로고
    • G protein- coupled receptor 30 (GPR30) mediates gene expression changes and growth response to 17beta-estradiol and selective GPR30 ligand G-1 in ovarian cancer cells
    • Albanito, L.; Madeo, A.; Lappano, R.; Vivacqua, A.; Rago, V.; Carpino, A.; Oprea, T.I.; Prossnitz, E.R.; Musti, A.M.; Andò, S.; Maggiolini, M. G protein- coupled receptor 30 (GPR30) mediates gene expression changes and growth response to 17beta-estradiol and selective GPR30 ligand G-1 in ovarian cancer cells. Cancer Res., 2007, 67, 1859-1866.
    • (2007) Cancer Res , vol.67 , pp. 1859-1866
    • Albanito, L.1    Madeo, A.2    Lappano, R.3    Vivacqua, A.4    Rago, V.5    Carpino, A.6    Oprea, T.I.7    Prossnitz, E.R.8    Musti, A.M.9    Andò, S.10    Maggiolini, M.11
  • 41
    • 78650845707 scopus 로고    scopus 로고
    • G protein-coupled receptors: Novel targets for drug discovery in cancer. Nat
    • Lappano, R.; Maggiolini, M. G protein-coupled receptors: novel targets for drug discovery in cancer. Nat. Rev. Drug Discov., 2011, 10, 47-60.
    • (2011) Rev. Drug Discov , vol.10 , pp. 47-60
    • Lappano, R.1    Maggiolini, M.2
  • 42
    • 84893437204 scopus 로고    scopus 로고
    • Novel insights into G protein and G protein-coupled receptor signaling in cancer
    • O'Hayre, M.; Degese, M.S.; Gutkind, J.S. Novel insights into G protein and G protein-coupled receptor signaling in cancer. Curr. Opin. Cell Biol., 2014, 27, 126-35.
    • (2014) Curr. Opin. Cell Biol , vol.27 , pp. 126-135
    • O'hayre, M.1    Degese, M.S.2    Gutkind, J.S.3
  • 43
    • 33751272253 scopus 로고    scopus 로고
    • Distribution of GPR30, a seven membranespanning estrogen receptor in primary breast cancer and its association with clinicopathologic determinants of tumor progression
    • Filardo, E.J.; Graeber, C.T.; Quinn, J.A.; Resnick, M.B.; Giri, D.; DeLellis, R.A.; Steinhoff, M.M.; Sabo, E. Distribution of GPR30, a seven membranespanning estrogen receptor in primary breast cancer and its association with clinicopathologic determinants of tumor progression. Clin. Cancer Res., 2006, 12, 6359-6366.
    • (2006) Clin. Cancer Res , vol.12 , pp. 6359-6366
    • Filardo, E.J.1    Graeber, C.T.2    Quinn, J.A.3    Resnick, M.B.4    Giri, D.5    Delellis, R.A.6    Steinhoff, M.M.7    Sabo, E.8
  • 46
    • 0033780783 scopus 로고    scopus 로고
    • Estrogen- induced activation of Erk-1 and Erk-2 requires the G proteincoupled receptor homolog, GPR30, and occurs via trans-activation of the epidermal growth factor receptor through release of HBEGF
    • J.r
    • Filardo, E.J.; Quinn, J.A.; Bland, K.I.; Frackelton, A.R. J.r. Estrogen- induced activation of Erk-1 and Erk-2 requires the G proteincoupled receptor homolog, GPR30, and occurs via trans-activation of the epidermal growth factor receptor through release of HBEGF. Mol. Endocrinol., 2000, 14, 1649-1660.
    • (2000) Mol. Endocrinol , vol.14 , pp. 1649-1660
    • Filardo, E.J.1    Quinn, J.A.2    Bland, K.I.3    Frackelton, A.R.4
  • 47
    • 33344461590 scopus 로고    scopus 로고
    • The G protein-coupled receptor GPR30 mediates the proliferative effects induced by 17ƒÀestradiol and hydroxytamoxifen in endometrial cancer cells
    • Vivacqua, A.; Bonofiglio, D.; Recchia, A.G.; Musti, A.M.; Picard, D.; Ando, S.; Maggiolini, M. The G protein-coupled receptor GPR30 mediates the proliferative effects induced by 17ƒÀestradiol and hydroxytamoxifen in endometrial cancer cells. Mol. Endocrinol., 2006, 20, 631-646.
    • (2006) Mol. Endocrinol , vol.20 , pp. 631-646
    • Vivacqua, A.1    Bonofiglio, D.2    Recchia, A.G.3    Musti, A.M.4    Picard, D.5    Ando, S.6    Maggiolini, M.7
  • 48
    • 33748923143 scopus 로고    scopus 로고
    • 17ƒÀ-Estradiol, genistein, and 4- hydroxytamoxifen induce the proliferation of thyroid cancer cells through the G protein coupledreceptor GPR30
    • Vivacqua, A.; Bonofiglio, D.; Albanito, L.; Madeo, A.; Rago, V.; Carpino, A.; Musti, A.M.; Picard, D.; Ando, S.; Maggiolini, M. 17ƒÀ-Estradiol, genistein, and 4- hydroxytamoxifen induce the proliferation of thyroid cancer cells through the G protein coupledreceptor GPR30. Mol. Pharmacol., 2006, 70, 1414-1423.
    • (2006) Mol. Pharmacol , vol.70 , pp. 1414-1423
    • Vivacqua, A.1    Bonofiglio, D.2    Albanito, L.3    Madeo, A.4    Rago, V.5    Carpino, A.6    Musti, A.M.7    Picard, D.8    Ando, S.9    Maggiolini, M.10
  • 49
    • 77955711650 scopus 로고    scopus 로고
    • Lau, K.M. Activation of GPR30 inhibits the growth of prostate cancer cells through sustained activation of Erk1/2, c-jun/c-fos-dependent upregulation of p21, and induction of G(2) cell-cycle arrest
    • Chan, Q.K.; Lam, H.M.; Ng, C.F.; Lee, A.Y.; Chan, E.S.; Ng, H.K.; Ho, S.M.; Lau, K.M. Activation of GPR30 inhibits the growth of prostate cancer cells through sustained activation of Erk1/2, c-jun/c-fos-dependent upregulation of p21, and induction of G(2) cell-cycle arrest. Cell. Death Differ., 2010, 17, 1511-1523.
    • (2010) Cell. Death Differ , vol.17 , pp. 1511-1523
    • Chan, Q.K.1    Lam, H.M.2    Ng, C.F.3    Lee, A.Y.4    Chan, E.S.5    Ng, H.K.6    Ho, S.M.7
  • 50
    • 79959887900 scopus 로고    scopus 로고
    • Role of GPER/GPR30 in tumoral testicular germ cells proliferation
    • Chevalier, N.; Bouskine, A.; Fenichel, P. Role of GPER/GPR30 in tumoral testicular germ cells proliferation. Cancer Biol. Ther., 2011, 12, 2-3.
    • (2011) Cancer Biol. Ther , vol.12 , pp. 2-3
    • Chevalier, N.1    Bouskine, A.2    Fenichel, P.3
  • 51
    • 0015342355 scopus 로고
    • Intercalation mechanisms: Antitumor drug design based upon helical DNA as a receptor site
    • Henry, D. Intercalation mechanisms: antitumor drug design based upon helical DNA as a receptor site. Cancer Chemother. Rep., 1972, 3, 50.
    • (1972) Cancer Chemother. Rep , vol.3
    • Henry, D.1
  • 53
    • 84862632433 scopus 로고    scopus 로고
    • Structural comparison of the interaction of tubulin with various ligands affecting microtubule dynamics
    • Stec-Martyna, E.; Ponassi, M.; Miele, M.; Parodi, S.; Felli, L.; Rosano, C. Structural comparison of the interaction of tubulin with various ligands affecting microtubule dynamics. Curr. Cancer Drug Targets., 2012, 12, 658-666.
    • (2012) Curr. Cancer Drug Targets , vol.12 , pp. 658-666
    • Stec-Martyna, E.1    Ponassi, M.2    Miele, M.3    Parodi, S.4    Felli, L.5    Rosano, C.6
  • 54
    • 77955613373 scopus 로고    scopus 로고
    • Small molecule antagonists of integrin receptors
    • Perdih, A.; Dolenc, M.S. Small molecule antagonists of integrin receptors. Curr. Med. Chem., 2010, 17, 2371-2392.
    • (2010) Curr. Med. Chem , vol.17 , pp. 2371-2392
    • Perdih, A.1    Dolenc, M.S.2
  • 56
    • 74049141810 scopus 로고    scopus 로고
    • In silico discovery of 2-amino-4-(2,4-dihydroxyphenyl)thiazoles as novel inhibitors of DNA gyrase B
    • Brvar, M.; Perdih, A.; Oblak, M.; Masic, L.P.; Solmajer, T. In silico discovery of 2-amino-4-(2,4-dihydroxyphenyl)thiazoles as novel inhibitors of DNA gyrase B. Bioorg. Med. Chem. Lett., 2010, 20, 958-962.
    • (2010) Bioorg. Med. Chem. Lett , vol.20 , pp. 958-962
    • Brvar, M.1    Perdih, A.2    Oblak, M.3    Masic, L.P.4    Solmajer, T.5
  • 57
    • 77249119272 scopus 로고    scopus 로고
    • Synthesis and characterization of iodinated tetrahydroquinolines targeting the G protein-coupled estrogen receptor GPR30
    • Ramesh, C.; Nayak, T.K.; Burai, R.; Dennis, M.K.; Hathaway, H.J.; Sklar, L.A.; Prossnitz, E.R.; Arterburn, J.B. Synthesis and characterization of iodinated tetrahydroquinolines targeting the G protein-coupled estrogen receptor GPR30. J. Med. Chem., 2010, 53, 1004-1014.
    • (2010) J. Med. Chem , vol.53 , pp. 1004-1014
    • Ramesh, C.1    Nayak, T.K.2    Burai, R.3    Dennis, M.K.4    Hathaway, H.J.5    Sklar, L.A.6    Prossnitz, E.R.7    Arterburn, J.B.8
  • 58
    • 84910622124 scopus 로고    scopus 로고
    • GPER-targeted, 99mTc-labeled, nonsteroidal ligands demonstrate selective tumor imaging and in vivo estrogen binding
    • Jul 16
    • Nayak, T.K.; Ramesh, C.; Hathaway, H.J.; Norenberg, J.P.; Arterburn, J.B.; Prossnitz, E.R. GPER-targeted, 99mTc-labeled, nonsteroidal ligands demonstrate selective tumor imaging and in vivo estrogen binding. Mol. Cancer Res., 2014 Jul 16.
    • (2014) Mol. Cancer Res
    • Nayak, T.K.1    Ramesh, C.2    Hathaway, H.J.3    Norenberg, J.P.4    Arterburn, J.B.5    Prossnitz, E.R.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.