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Volumn 4, Issue 2, 2010, Pages 115-123

Cembrene diterpenoids: Conformational studies and molecular docking to tubulin

Author keywords

Cembrenes; Conformations; Molecular docking; Tubulin

Indexed keywords

CASBENE; CEMBRENE; CEMBRENE A; COLCHICINE; DITERPENOID; ISOCEMBRENE; ISOCENSOLE; PACLITAXEL; PODOPHYLLOTOXIN; TUBULIN; UNCLASSIFIED DRUG; VINBLASTINE;

EID: 77955465145     PISSN: None     EISSN: 13076167     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (9)

References (36)
  • 1
    • 0038219851 scopus 로고
    • Cembrene, a fourteen-membered ring diterpene hydrocarbon
    • W.G. Dauben, W.E. Thiessen and P.R. Resnick (1965). Cembrene, a fourteen-membered ring diterpene hydrocarbon. J. Org. Chem. 30, 1693-1698.
    • (1965) J. Org. Chem , vol.30 , pp. 1693-1698
    • Dauben, W.G.1    Thiessen, W.E.2    Resnick, P.R.3
  • 2
    • 0000048444 scopus 로고
    • Chemistry of Ayurvedic crude drugs - II: Guggulu (resin from Commiphora mukul)-2: Diterpenoid constituents
    • V.D. Patil, U.R. Nayak and S. Dev (1973). Chemistry of Ayurvedic crude drugs - II: Guggulu (resin from Commiphora mukul)-2: Diterpenoid constituents. Tetrahedron 29, 341-348.
    • (1973) Tetrahedron , vol.29 , pp. 341-348
    • Patil, V.D.1    Nayak, U.R.2    Dev, S.3
  • 3
    • 20444371942 scopus 로고    scopus 로고
    • A chemical investigation by headspace SPME and GC-MS of volatile and semi-volatile terpenes in various olibanum samples
    • S. Hamm, J. Bleton, J. Connan and A. Tchapla (2005). A chemical investigation by headspace SPME and GC-MS of volatile and semi-volatile terpenes in various olibanum samples. Phytochemistry 66, 1499-1514.
    • (2005) Phytochemistry , vol.66 , pp. 1499-1514
    • Hamm, S.1    Bleton, J.2    Connan, J.3    Tchapla, A.4
  • 4
    • 37049132610 scopus 로고
    • Neocembrene-A, a termite train pheromone
    • Perkin Trans. I
    • A.J. Birch, W.V. Brown, J.E.T. Corrie and B.P. Moore (1972). Neocembrene-A, a termite train pheromone. J. Chem. Soc., Perkin Trans. I 2653-2658.
    • (1972) J. Chem. Soc , pp. 2653-2658
    • Birch, A.J.1    Brown, W.V.2    Corrie, J.E.T.3    Moore, B.P.4
  • 5
    • 0343748937 scopus 로고
    • Identification and source of a queen-specific chemical in the Pharaoh's ant, Monomorium pharaonis (L.)
    • J.P. Edwards and J. Chambers (1984). Identification and source of a queen-specific chemical in the Pharaoh's ant, Monomorium pharaonis (L.). J. Chem. Ecol. 10, 1731-1747.
    • (1984) J. Chem. Ecol , vol.10 , pp. 1731-1747
    • Edwards, J.P.1    Chambers, J.2
  • 6
    • 0000640114 scopus 로고
    • Marine natural products: Cembrene-A and cembrene-C from a soft coral, Nephthea sp
    • D.J. Vanderah, N. Rutledge, F.J. Schmitz and L.S. Ciereszko (1978). Marine natural products: Cembrene-A and cembrene-C from a soft coral, Nephthea sp. J. Org. Chem. 43, 1614-1616.
    • (1978) J. Org. Chem , vol.43 , pp. 1614-1616
    • Vanderah, D.J.1    Rutledge, N.2    Schmitz, F.J.3    Ciereszko, L.S.4
  • 7
    • 0032709550 scopus 로고    scopus 로고
    • Cytotoxic terpenoids from the Formosan soft coral Nephthea brassica
    • C.Y. Duh, S.K. Wang, Y.L. Weng, M.Y. Chiang and C.F. Dai (1999). Cytotoxic terpenoids from the Formosan soft coral Nephthea brassica. J. Nat. Prod. 62, 1518-1521.
    • (1999) J. Nat. Prod , vol.62 , pp. 1518-1521
    • Duh, C.Y.1    Wang, S.K.2    Weng, Y.L.3    Chiang, M.Y.4    Dai, C.F.5
  • 8
    • 0030850193 scopus 로고    scopus 로고
    • Cembrene A and a congeneric ketone isolated from the paracloacal glands of the Chinese alligator (Alligator sinensis)
    • D.L. Mattern, W.D. Scott, C.A. McDaniel, P.J. Weldon and D.E. Graves (1997). Cembrene A and a congeneric ketone isolated from the paracloacal glands of the Chinese alligator (Alligator sinensis). J. Nat. Prod. 60, 828-831.
    • (1997) J. Nat. Prod , vol.60 , pp. 828-831
    • Mattern, D.L.1    Scott, W.D.2    McDaniel, C.A.3    Weldon, P.J.4    Graves, D.E.5
  • 9
    • 2742514692 scopus 로고
    • Cembrene A and (3Z)-cembrene A: Diterpenes from a termite soldier (Isoptera Termitidae Termitinae)
    • D.F. Wiemer, J. Meinwald, G.D. Prestwich and I. Miura (1979). Cembrene A and (3Z)-cembrene A: Diterpenes from a termite soldier (Isoptera Termitidae Termitinae). J. Org. Chem. 44, 3950-3952.
    • (1979) J. Org. Chem , vol.44 , pp. 3950-3952
    • Wiemer, D.F.1    Meinwald, J.2    Prestwich, G.D.3    Miura, I.4
  • 11
    • 0009250210 scopus 로고
    • Conformational analysis of cyclic terpenes: Application of computational and experimental (NMR) methods
    • C. Müller, M.A. Liping and P. Bigler (1994). Conformational analysis of cyclic terpenes: Application of computational and experimental (NMR) methods. J. Mol. Struct. THEOCHEM 308, 25-36.
    • (1994) J. Mol. Struct. THEOCHEM , vol.308 , pp. 25-36
    • Müller, C.1    Liping, M.A.2    Bigler, P.3
  • 12
    • 0342656310 scopus 로고
    • Cyclization of polyenes XXV. Conformational study of cembrene type diterpenes by X-ray analysis
    • T. Kato, C. Kabuto, K.H. Kim, H. Takayanagi, T. Uyehara and Y. Kitahara (1977). Cyclization of polyenes XXV. Conformational study of cembrene type diterpenes by X-ray analysis. Chem. Lett. 827-830.
    • (1977) Chem. Lett , pp. 827-830
    • Kato, T.1    Kabuto, C.2    Kim, K.H.3    Takayanagi, H.4    Uyehara, T.5    Kitahara, Y.6
  • 13
    • 0013513108 scopus 로고
    • Conformational analysis of the 10- and 13-hydroxy derivatives of cembrene
    • A.V. Vorobjev, M.M. Shakirov, V.A. Raldugin and C.H. Heathcock (1995). Conformational analysis of the 10- and 13-hydroxy derivatives of cembrene. J. Org. Chem. 60, 63-69.
    • (1995) J. Org. Chem , vol.60 , pp. 63-69
    • Vorobjev, A.V.1    Shakirov, M.M.2    Raldugin, V.A.3    Heathcock, C.H.4
  • 14
    • 0031872051 scopus 로고    scopus 로고
    • Tubulin as a target for anticancer drugs: Agents which interact with the mitotic spindle
    • A. Jordan, J.A. Hadfield, N.J. Lawrence and A.T. McGown (1998). Tubulin as a target for anticancer drugs: Agents which interact with the mitotic spindle. Med. Res. Rev. 18, 259-296.
    • (1998) Med. Res. Rev , vol.18 , pp. 259-296
    • Jordan, A.1    Hadfield, J.A.2    Lawrence, N.J.3    McGown, A.T.4
  • 15
    • 1942438028 scopus 로고    scopus 로고
    • Microtubules as a target for anticancer drugs
    • M.A. Jordan and L. Wilson (2004). Microtubules as a target for anticancer drugs. Nat. Rev. Cancer 4, 253-265.
    • (2004) Nat. Rev. Cancer , vol.4 , pp. 253-265
    • Jordan, M.A.1    Wilson, L.2
  • 16
    • 20044379059 scopus 로고    scopus 로고
    • Review: Tubulin function, action of antitubulin drugs, and new drug development
    • F. Pellegrini and D.R. Budman (2005). Review: Tubulin function, action of antitubulin drugs, and new drug development. Cancer Invest. 23, 264-273.
    • (2005) Cancer Invest , vol.23 , pp. 264-273
    • Pellegrini, F.1    Budman, D.R.2
  • 17
    • 65349097586 scopus 로고    scopus 로고
    • Tubulin-interactive natural products as anticancer agents
    • D.G.I. Kingston (2009). Tubulin-interactive natural products as anticancer agents. J. Nat. Prod. 72, 507-515.
    • (2009) J. Nat. Prod , vol.72 , pp. 507-515
    • Kingston, D.G.I.1
  • 18
    • 0020698663 scopus 로고
    • Latrunculins: Novel marine toxins that disrupt microfilament organization in cultured cells
    • I. Spector, N.R. Shochet, Y. Kashman and A. Groweiss (1983). Latrunculins: novel marine toxins that disrupt microfilament organization in cultured cells. Science 219, 493-495.
    • (1983) Science , vol.219 , pp. 493-495
    • Spector, I.1    Shochet, N.R.2    Kashman, Y.3    Groweiss, A.4
  • 19
    • 0021180180 scopus 로고
    • Studies on macrocyclic lactone antibiotics VII. Structure of a phytotoxin "rhizoxin" produced by Rhizopus chinensis
    • S. Iwasaki, H. Kobayashi, J. Furukawa, M. Namikoshi, S. Okuda, Z. Sato, I. Matsuda and T. Noda (1984). Studies on macrocyclic lactone antibiotics VII. Structure of a phytotoxin "rhizoxin" produced by Rhizopus chinensis. J. Antibiot. 37, 354-362.
    • (1984) J. Antibiot , vol.37 , pp. 354-362
    • Iwasaki, S.1    Kobayashi, H.2    Furukawa, J.3    Namikoshi, M.4    Okuda, S.5    Sato, Z.6    Matsuda, I.7    Noda, T.8
  • 21
    • 0030018666 scopus 로고    scopus 로고
    • Epothilons A and B: Antifungal and cytotoxic compounds from Sorangium cellulosum (Myxobacteria)
    • K. Gerth, N. Bedorf, G. Höfle, G. Irschik and H. Reichenbach (1996). Epothilons A and B: Antifungal and cytotoxic compounds from Sorangium cellulosum (Myxobacteria). J. Antibiot. 49, 560-563.
    • (1996) J. Antibiot , vol.49 , pp. 560-563
    • Gerth, K.1    Bedorf, N.2    Höfle, G.3    Irschik, G.4    Reichenbach, H.5
  • 24
    • 0033083045 scopus 로고    scopus 로고
    • Laulimalide and isolaulimalide, new paclitaxel-like microtubule-stabilizing agents
    • S.L. Mooberry, G. Tien, A.H. Hernandez, A. Plubrukar and B.S. Davidson (1999). Laulimalide and isolaulimalide, new paclitaxel-like microtubule-stabilizing agents. Cancer Res. 59, 653-660.
    • (1999) Cancer Res , vol.59 , pp. 653-660
    • Mooberry, S.L.1    Tien, G.2    Hernandez, A.H.3    Plubrukar, A.4    Davidson, B.S.5
  • 25
    • 60849122543 scopus 로고    scopus 로고
    • Toward docking-based virtual screening for discovering antitubulin agents by targeting taxane and colchicine binding sites
    • L. Soulère (2009). Toward docking-based virtual screening for discovering antitubulin agents by targeting taxane and colchicine binding sites. ChemMedChem 4, 161-163.
    • (2009) ChemMedChem , vol.4 , pp. 161-163
    • Soulère, L.1
  • 26
    • 33645284484 scopus 로고    scopus 로고
    • SPARTAN'08 for Windows, v. 1.2, Irvine, California, USA
    • SPARTAN'08 for Windows, v. 1.2 (2008). Wavefunction, Inc. Irvine, California, USA.
    • (2008) Wavefunction, Inc
  • 27
    • 0037571112 scopus 로고    scopus 로고
    • Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF 94
    • T.A. Halgren (1996). Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF 94. J. Comput. Chem. 17, 490-519.
    • (1996) J. Comput. Chem , vol.17 , pp. 490-519
    • Halgren, T.A.1
  • 28
    • 0000189651 scopus 로고
    • Density-functional thermochemistry. III. The role of exact exchange
    • A.D. Becke (1993). Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 98, 5648-5652.
    • (1993) J. Chem. Phys , vol.98 , pp. 5648-5652
    • Becke, A.D.1
  • 29
    • 0345491105 scopus 로고
    • Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density
    • C. Lee, W. Yang and R.G. Parr (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 37, 785-789.
    • (1988) Phys. Rev. B , vol.37 , pp. 785-789
    • Lee, C.1    Yang, W.2    Parr, R.G.3
  • 31
    • 1642401199 scopus 로고    scopus 로고
    • Insight into tubulin regulation from a complex with colchicine and a stathmin-like domain
    • R.B. Ravelli, B. Gigant, P.A. Curmi, I. Jourdain, S. Lachkar, A. Sobel and M. Knossow (2004). Insight into tubulin regulation from a complex with colchicine and a stathmin-like domain. Nature 428, 198-202.
    • (2004) Nature , vol.428 , pp. 198-202
    • Ravelli, R.B.1    Gigant, B.2    Curmi, P.A.3    Jourdain, I.4    Lachkar, S.5    Sobel, A.6    Knossow, M.7
  • 32
    • 0035834521 scopus 로고    scopus 로고
    • Refined structure of αβ-tubulin at 3.5 Å resolution
    • J. Löwe, H. Li, K.H. Downing and E. Nogales (2001). Refined structure of αβ-tubulin at 3.5 Å resolution. J. Mol. Biol. 313, 1045-1057.
    • (2001) J. Mol. Biol , vol.313 , pp. 1045-1057
    • Löwe, J.1    Li, H.2    Downing, K.H.3    Nogales, E.4
  • 34
    • 77955440679 scopus 로고    scopus 로고
    • Molegro Virtual Docker v. 4.0, Aarhus, Denmark
    • Molegro Virtual Docker v. 4.0 (2009). Molegro ApS. Aarhus, Denmark.
    • (2009) Molegro ApS
  • 35
    • 33744826819 scopus 로고    scopus 로고
    • MolDock: A new technique for high-accuracy molecular docking
    • R. Thomsen and M.H. Christensen (2006). MolDock: A new technique for high-accuracy molecular docking. J. Med. Chem. 49, 3315-3321.
    • (2006) J. Med. Chem , vol.49 , pp. 3315-3321
    • Thomsen, R.1    Christensen, M.H.2
  • 36
    • 0040286118 scopus 로고
    • The crystal and molecular structure of cembrene
    • M.G.B. Drew, D.H. Templeton and A. Zalkin (1969). The crystal and molecular structure of cembrene. Acta Crystallogr. B25, 261-267.
    • (1969) Acta Crystallogr , vol.B25 , pp. 261-267
    • Drew, M.G.B.1    Templeton, D.H.2    Zalkin, A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.