메뉴 건너뛰기




Volumn 53, Issue 3, 2010, Pages 1004-1014

Synthesis and characterization of iodinated tetrahydroquinolines targeting the G protein-coupled estrogen receptor GPR30

Author keywords

[No Author keywords available]

Indexed keywords

1 (4 (6 BROMOBENZO[D][1,3]DIOXOL 5 YL) 6 IODO 3A,4,5,9B TETRAHYDRO 3H CYCLOPENTA[C]QUINOLIN 8 YL)ETHANONE; 1 [4 (6 IODOBENZO[1,3]DIOXOL 5 YL) 3A,4,5,9B TETRAHYDRO 3H CYCLOPENTA[C]QUINOLIN 8 YL]ETHANONE; 1 {2 [4 (6 BROMOBENZO[1,3]DIOXOL 5 YL) 3A,4,5,9B TETRAHYDRO 3H CYCLOPENTA[C]QUINOLIN 8 YL]ETHYL} 3 (3 IODOPHENYL)UREA; 4 (6 BROMOBENZO[1,3]DIOXOL 5 YL) 7 IODO 3A,4,5,9B TETRAHYDRO 3H CYCLOPENTA[C]QUINOLINE; 4 (6 BROMOBENZO[1,3]DIOXOL 5 YL) 8 IODO 3A,4,5,9B TETRAHYDRO 3H CYCLOPENTA[C]QUINOLINE; ESTROGEN RECEPTOR; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; G PROTEIN COUPLED ESTROGEN RECEPTOR; G PROTEIN COUPLED RECEPTOR; IODINE 125; N {1 [4 (6 BROMOBENZO[1,3]DIOXOL 5 YL) 3A,4,5,9B TETRAHYDRO 3H CYCLOPENTA[C]QUINOLIN 8 YL]ETHYLIDENE} N' (5 IODOPYRIDIN 2 YL) HYDRAZINE; N {2 [4 (6 BROMOBENZO[1,3]DIOXOL 5 YL) 3A,4,5,9B TETRAHYDRO 3H CYCLOPENTA[C]QUINOLIN 8 YL]ETHYL} 4 IODOBENZAMIDE; PHOSPHATIDYLINOSITOL 3 KINASE; QUINOLINE DERIVATIVE; TETRAHYDRO 3H CYCLOPENTA[C]QUINOLINE; TRACER; UNCLASSIFIED DRUG;

EID: 77249119272     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm9011802     Document Type: Article
Times cited : (52)

References (46)
  • 1
    • 15744393640 scopus 로고    scopus 로고
    • Regulation of signal transduction pathways by estrogen and progesterone
    • Edwards, D. P. Regulation of signal transduction pathways by estrogen and progesterone. Annu. Rev. Physiol. 2005, 67, 335-376.
    • (2005) Annu. Rev. Physiol , vol.67 , pp. 335-376
    • Edwards, D.P.1
  • 2
    • 33947401482 scopus 로고    scopus 로고
    • Integration of rapid signaling events with steroid hormone receptor action in breast and prostate cancer
    • Lange, C. A.; Gioeli, D.; Hammes, S. R.; Marker, P. C. Integration of rapid signaling events with steroid hormone receptor action in breast and prostate cancer. Annu. Rev. Physiol. 2007, 69, 171-199.
    • (2007) Annu. Rev. Physiol , vol.69 , pp. 171-199
    • Lange, C.A.1    Gioeli, D.2    Hammes, S.R.3    Marker, P.C.4
  • 3
    • 77249173325 scopus 로고    scopus 로고
    • http://www.iuphar-db.org/GPCR/ReceptorDisplayForward?receptorID=3055.
  • 4
    • 0033780783 scopus 로고    scopus 로고
    • Estrogen-induced activation of Erk-1 and Erk-2 requires the G protein-coupled receptor homolog, GPR30, and occurs via trans-activation of the epidermal growth factor receptor through release of HB-EGF
    • Filardo, E. J.; Quinn, J. A.; Bland, K. I; Frackelton, A. R., Jr. Estrogen-induced activation of Erk-1 and Erk-2 requires the G protein-coupled receptor homolog, GPR30, and occurs via trans-activation of the epidermal growth factor receptor through release of HB-EGF. 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 Jr., A.R.4
  • 5
    • 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
  • 6
    • 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
  • 9
    • 33751272253 scopus 로고    scopus 로고
    • Distribution of GPR30, a seven membrane-spanning 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 membrane-spanning 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
  • 10
    • 33947697810 scopus 로고    scopus 로고
    • Smith, H. O.; Leslie, K. K.; Singh, M.; Qualls, C. R.; Revankar,C. M.; Joste, N. E.; Prossnitz, E. R. GPR30: a novel indicator of poor survival for endometrial carcinoma. Am. J. Obstet. Gynecol. 2007, 196, 386.e1-386.e11.
    • Smith, H. O.; Leslie, K. K.; Singh, M.; Qualls, C. R.; Revankar,C. M.; Joste, N. E.; Prossnitz, E. R. GPR30: a novel indicator of poor survival for endometrial carcinoma. Am. J. Obstet. Gynecol. 2007, 196, 386.e1-386.e11.
  • 11
    • 0034466972 scopus 로고    scopus 로고
    • Estrogen receptor transcription and transactivation: Estrogen receptor alpha and estrogen receptor beta: regulation by selective estrogen receptor modulators and importance in breast cancer
    • Katzenellenbogen, B. S.; Katzenellenbogen, J. A. Estrogen receptor transcription and transactivation: estrogen receptor alpha and estrogen receptor beta: regulation by selective estrogen receptor modulators and importance in breast cancer. Breast Cancer Res. 2000, 2, 335-344.
    • (2000) Breast Cancer Res , vol.2 , pp. 335-344
    • Katzenellenbogen, B.S.1    Katzenellenbogen, J.A.2
  • 14
    • 33847755409 scopus 로고    scopus 로고
    • G protein-coupled receptor 30 (GPR30) mediates gene expression changes and growth response to 17β-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.; Ando, S.; Maggiolini, M. G protein-coupled receptor 30 (GPR30) mediates gene expression changes and growth response to 17β-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    Ando, S.10    Maggiolini, M.11
  • 15
    • 34250322219 scopus 로고    scopus 로고
    • Distribution and characterization of estrogen receptor G protein-coupled receptor 30 in the rat central nervous system
    • Brailoiu, E.; Dun, S. L.; Brailoiu, G. C.; Mizuo, K.; Sklar, L. A.; Oprea, T. I.; Prossnitz, E. R.; Dun, N. J. Distribution and characterization of estrogen receptor G protein-coupled receptor 30 in the rat central nervous system. J. Endocrinol. 2007, 193, 311-321.
    • (2007) J. Endocrinol , vol.193 , pp. 311-321
    • Brailoiu, E.1    Dun, S.L.2    Brailoiu, G.C.3    Mizuo, K.4    Sklar, L.A.5    Oprea, T.I.6    Prossnitz, E.R.7    Dun, N.J.8
  • 16
    • 46349096631 scopus 로고    scopus 로고
    • Estrogen signaling characteristics of Atlantic Croaker G protein-coupled receptor 30 (GPR30) and evidence it is involved in maintenance of oocyte meiotic arrest
    • Pang, Y.; Dong, J.; Thomas, T. Estrogen signaling characteristics of Atlantic Croaker G protein-coupled receptor 30 (GPR30) and evidence it is involved in maintenance of oocyte meiotic arrest. Endocrinology 2008, 149, 3410-3426.
    • (2008) Endocrinology , vol.149 , pp. 3410-3426
    • Pang, Y.1    Dong, J.2    Thomas, T.3
  • 18
    • 47949092800 scopus 로고    scopus 로고
    • The G protein-coupled receptor GPR30 inhibits human urothelial cell proliferation
    • Teng, J.; Wang, Z.-Y.; Prossnitz, E. R.; Bjorling, D. E. The G protein-coupled receptor GPR30 inhibits human urothelial cell proliferation. Endocrinology 2008, 149, 4024-4034.
    • (2008) Endocrinology , vol.149 , pp. 4024-4034
    • Teng, J.1    Wang, Z.-Y.2    Prossnitz, E.R.3    Bjorling, D.E.4
  • 19
    • 53249101612 scopus 로고    scopus 로고
    • The novel estrogen receptor, G protein-coupled receptor 30, mediates the proliferative effects induced by 17β-estradiol on mouse spermatogonial GC-1 cell line
    • Sirianni, R.; Chimento, A.; Ruggiero, C.; Luca, A. D.; Lappano, R.; Ando, S.; Maggiolini, M.; Pezzi, V. The novel estrogen receptor, G protein-coupled receptor 30, mediates the proliferative effects induced by 17β-estradiol on mouse spermatogonial GC-1 cell line. Endocrinology 2008, 149, 5043-5051.
    • (2008) Endocrinology , vol.149 , pp. 5043-5051
    • Sirianni, R.1    Chimento, A.2    Ruggiero, C.3    Luca, A.D.4    Lappano, R.5    Ando, S.6    Maggiolini, M.7    Pezzi, V.8
  • 23
    • 50949130709 scopus 로고    scopus 로고
    • Potential role of G-protein-coupled receptor 30 (GPR30) in estradiol-17β-stimulated IGF-I mRNA expression in bovine satellite cell cultures
    • Kamanga-Sollo, E.; White, M. E.; Chung, K. Y.; Johnson, B. J.; Dayton, W. R. Potential role of G-protein-coupled receptor 30 (GPR30) in estradiol-17β-stimulated IGF-I mRNA expression in bovine satellite cell cultures. Domest. Anim. Endocrinol. 2008, 35, 254-262.
    • (2008) Domest. Anim. Endocrinol , vol.35 , pp. 254-262
    • Kamanga-Sollo, E.1    White, M.E.2    Chung, K.Y.3    Johnson, B.J.4    Dayton, W.R.5
  • 27
    • 0018826511 scopus 로고
    • 125I]iodo-estradiol with estrogen receptor and other steroid-binding proteins
    • 125I]iodo-estradiol with estrogen receptor and other steroid-binding proteins. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 328-332.
    • (1980) Proc. Natl. Acad. Sci. U.S.A , vol.77 , pp. 328-332
    • Hochberg, R.B.1    Rosner, W.2
  • 28
    • 0018833905 scopus 로고
    • Receptor-binding radiopharmaceuticals for imaging breast tumors: Estrogen-receptor interactions and selectivity of tissue uptake of halogenated estrogen analogs
    • Katzenellenbogen, J. A.; Carlson, K. E.; Heiman, D. F.; Goswami, R. Receptor-binding radiopharmaceuticals for imaging breast tumors: estrogen-receptor interactions and selectivity of tissue uptake of halogenated estrogen analogs. J. Nucl. Med. 1980, 21, 550-558.
    • (1980) J. Nucl. Med , vol.21 , pp. 550-558
    • Katzenellenbogen, J.A.1    Carlson, K.E.2    Heiman, D.F.3    Goswami, R.4
  • 29
    • 0027230247 scopus 로고
    • Radiolabeled steroidal estrogens in cancer research
    • Cummins, C. H. Radiolabeled steroidal estrogens in cancer research. Steroids 1993, 58, 245-259.
    • (1993) Steroids , vol.58 , pp. 245-259
    • Cummins, C.H.1
  • 30
    • 0033866460 scopus 로고    scopus 로고
    • Synthesis of Auger electron-emitting radiopharmaceuticals
    • Hanson, R. N. Synthesis of Auger electron-emitting radiopharmaceuticals. Curr. Pharm. Des. 2000, 6, 1457-1468.
    • (2000) Curr. Pharm. Des , vol.6 , pp. 1457-1468
    • Hanson, R.N.1
  • 33
    • 33846921573 scopus 로고    scopus 로고
    • The positron emission tomography with F18 17β-estradiol has the potential to benefit diagnosis and treatment of endometrial cancer
    • Yoshida, Y.; Kurokawa, T.; Sawamura, Y.; Shinagawa, A.; Okazawa, H.; Fujibayashi, Y.; Kotsuji, F. The positron emission tomography with F18 17β-estradiol has the potential to benefit diagnosis and treatment of endometrial cancer. Gynecol. Oncol. 2007, 104, 764-766.
    • (2007) Gynecol. Oncol , vol.104 , pp. 764-766
    • Yoshida, Y.1    Kurokawa, T.2    Sawamura, Y.3    Shinagawa, A.4    Okazawa, H.5    Fujibayashi, Y.6    Kotsuji, F.7
  • 34
    • 26444610710 scopus 로고    scopus 로고
    • 18F]fluoro-17β-estradiol. J. Med. Chem. 2005, 48, 6366-6378.
    • 18F]fluoro-17β-estradiol. J. Med. Chem. 2005, 48, 6366-6378.
  • 37
    • 57349150349 scopus 로고    scopus 로고
    • Diethylstilbestrol (DES) labeled with Auger emitters: Potential radiopharmaceutical for therapy of estrogen receptor-positive tumors and their metastases?
    • Fischer, T.; Schomacker, K.; Schicha, H. Diethylstilbestrol (DES) labeled with Auger emitters: potential radiopharmaceutical for therapy of estrogen receptor-positive tumors and their metastases? Int. J. Radiat. Biol. 2008, 84, 1112-1122.
    • (2008) Int. J. Radiat. Biol , vol.84 , pp. 1112-1122
    • Fischer, T.1    Schomacker, K.2    Schicha, H.3
  • 38
    • 61349084177 scopus 로고    scopus 로고
    • Recent synthetic developments in a powerful imino Diels-Alder reaction (Povarov reaction): Application to the synthesis of N-polyheterocycles and related alkaloids
    • Kouznetsov, V. V. Recent synthetic developments in a powerful imino Diels-Alder reaction (Povarov reaction): application to the synthesis of N-polyheterocycles and related alkaloids. Tetrahedron 2009, 6, 2721-2750.
    • (2009) Tetrahedron , vol.6 , pp. 2721-2750
    • Kouznetsov, V.V.1
  • 39
    • 0036625262 scopus 로고    scopus 로고
    • Rare-earth metal triflates in organic synthesis
    • Kobayashi, S.; Sugiura, M.; Kitagawa, H.; Lam, W. W.-L. Rare-earth metal triflates in organic synthesis. Chem. Rev. 2002, 102, 2227-2302.
    • (2002) Chem. Rev , vol.102 , pp. 2227-2302
    • Kobayashi, S.1    Sugiura, M.2    Kitagawa, H.3    Lam, W.W.-L.4
  • 40
    • 0023022561 scopus 로고
    • Synthesis of (pyridinyl)-1,2,4-triazolo[4,3-α]pyridines
    • Moran, D. B.; Morton, G. O.; Albright, J. D. Synthesis of (pyridinyl)-1,2,4-triazolo[4,3-α]pyridines. J. Heterocycl. Chem. 1986, 23, 1071-1077.
    • (1986) J. Heterocycl. Chem , vol.23 , pp. 1071-1077
    • Moran, D.B.1    Morton, G.O.2    Albright, J.D.3
  • 41
    • 0032547897 scopus 로고    scopus 로고
    • Hanson, R. N.; Napolitano, E.; Fiaschi, R. Synthesis and evaluation of 11β-substituted 21-choloro/iodo-(17α,20E/Z)-19-norpregna-1,3, 5(10),20-tetraene-3,17β-diols: high affinity ligands for the estrogen receptor. J. Med. Chem. 1998, 41, 4686-4692.
    • Hanson, R. N.; Napolitano, E.; Fiaschi, R. Synthesis and evaluation of 11β-substituted 21-choloro/iodo-(17α,20E/Z)-19-norpregna-1,3, 5(10),20-tetraene-3,17β-diols: high affinity ligands for the estrogen receptor. J. Med. Chem. 1998, 41, 4686-4692.
  • 42
    • 0034607005 scopus 로고    scopus 로고
    • Novel 17α- ethynylestradiol derivatives: Sonogashira couplings using unprotected phenylhydrazines
    • Arterburn, J. B.; Rao, K. B.; Perry, M. C. Novel 17α- ethynylestradiol derivatives: Sonogashira couplings using unprotected phenylhydrazines. Tetrahedron Lett. 2000, 41, 839-842.
    • (2000) Tetrahedron Lett , vol.41 , pp. 839-842
    • Arterburn, J.B.1    Rao, K.B.2    Perry, M.C.3
  • 43
    • 0032499084 scopus 로고    scopus 로고
    • α-Iodocycloalkenones: Synthesis of (±)- epibatidine
    • Sirisoma, N. S.; Johnson, C. R. α-Iodocycloalkenones: synthesis of (±)- epibatidine. Tetrahedron Lett. 1998, 39, 2059-2062.
    • (1998) Tetrahedron Lett , vol.39 , pp. 2059-2062
    • Sirisoma, N.S.1    Johnson, C.R.2
  • 44
    • 45549102860 scopus 로고    scopus 로고
    • 123I]I-PK11195, a single photon emission computed tomography tracer for peripheral benzodiazepine receptors
    • 123I]I-PK11195, a single photon emission computed tomography tracer for peripheral benzodiazepine receptors. Nucl. Med. Biol. 2008, 35, 537-542.
    • (2008) Nucl. Med. Biol , vol.35 , pp. 537-542
    • Pimlott, S.1    Stevenson, L.2    Wyper, D.3    Sutherland, A.4
  • 45
    • 33751004697 scopus 로고    scopus 로고
    • 99mTc(I) chelates. J. Am. Chem. Soc. 2006, 128, 14476-14477.
    • 99mTc(I) chelates. J. Am. Chem. Soc. 2006, 128, 14476-14477.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.