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Volumn 41, Issue 9, 1998, Pages 1476-1496

Clarification of the binding mode of teleocidin and benzolactams to the Cys2 domain of protein kinase Cδ by synthesis of hydrophobically modified, teleocidin-mimicking benzolactams and computational docking simulation

Author keywords

[No Author keywords available]

Indexed keywords

BENZOLACTAM; LACTAM DERIVATIVE; PHORBOL 13 ACETATE 12 MYRISTATE; PHORBOL ESTER; TELEOCIDIN; UNCLASSIFIED DRUG;

EID: 0032560190     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970704s     Document Type: Article
Times cited : (40)

References (62)
  • 2
    • 0000844430 scopus 로고
    • Indole alkaloids: Dihydroteleocidin B, teleocidin, and lyngbyatoxin. Members of a new class of tumor promoters
    • (b) Fujiki, H.; Mori, M.; Nakayasu, M.; Terada, M.; Sugimura, T.; Moore, R. E. Indole alkaloids: Dihydroteleocidin B, teleocidin, and lyngbyatoxin. Members of a new class of tumor promoters. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 3872-3876.
    • (1981) Proc. Natl. Acad. Sci. U.S.A. , vol.78 , pp. 3872-3876
    • Fujiki, H.1    Mori, M.2    Nakayasu, M.3    Terada, M.4    Sugimura, T.5    Moore, R.E.6
  • 3
    • 0020356226 scopus 로고
    • Molecular requirements for epigenetic modulators. Synthesis of active fragment of teleocidins and lyngbyatoxin
    • (a) Endo, Y.; Shudo, K.; Okamoto, T. Molecular requirements for epigenetic modulators. Synthesis of active fragment of teleocidins and lyngbyatoxin. Chem. Pharm. Bull. 1982, 30, 3457-3460.
    • (1982) Chem. Pharm. Bull. , vol.30 , pp. 3457-3460
    • Endo, Y.1    Shudo, K.2    Okamoto, T.3
  • 4
    • 85004366023 scopus 로고
    • Synthesis of optically active teleocidin derivatives. Absolute configuration of teleocidin B and olivoretin A
    • (b) Endo, Y.; Shudo, K.; Furuhata, K.; Ogura, H.; Sakai, S.; Aimi, N.; Hitotsuyanagi, Y.; Koyama, Y. Synthesis of optically active teleocidin derivatives. Absolute configuration of teleocidin B and olivoretin A. Chem. Pharm. Bull. 1984, 32, 358-361.
    • (1984) Chem. Pharm. Bull. , vol.32 , pp. 358-361
    • Endo, Y.1    Shudo, K.2    Furuhata, K.3    Ogura, H.4    Sakai, S.5    Aimi, N.6    Hitotsuyanagi, Y.7    Koyama, Y.8
  • 5
    • 0021258634 scopus 로고
    • The Epstein-Barr virus early antigen inducing indole alkaloids, (-)-indolactam-V and its related compounds, produced by Actinomycetes
    • Irie, K.; Hirota, M.; Hagiwara, N.; Koshimizu, K.; Hayashi, H.; Murao, S.; Tokuda, H.; Ito, Y. The Epstein-Barr virus early antigen inducing indole alkaloids, (-)-indolactam-V and its related compounds, produced by Actinomycetes. Agric. Biol. Chem. 1984, 48, 1269-1274.
    • (1984) Agric. Biol. Chem. , vol.48 , pp. 1269-1274
    • Irie, K.1    Hirota, M.2    Hagiwara, N.3    Koshimizu, K.4    Hayashi, H.5    Murao, S.6    Tokuda, H.7    Ito, Y.8
  • 7
    • 0022892576 scopus 로고
    • Synthetic approaches to the teleocidin-related tumor promoters. A total synthesis of indolactam-V
    • (a) deLaszlo, S. E.; Ley, S. V.; Porter, R. A. J. Synthetic approaches to the teleocidin-related tumor promoters. A total synthesis of indolactam-V. J. Chem. Soc. Chem. Commun. 1986, 344-346.
    • (1986) J. Chem. Soc. Chem. Commun. , pp. 344-346
    • DeLaszlo, S.E.1    Ley, S.V.2    Porter, R.A.J.3
  • 8
    • 0344965061 scopus 로고
    • Efficient syntheses and chemistry of indolactam-V and its analogues
    • (b) Matsuda, T.; Nakatsuka, S.; Goto, T. Efficient syntheses and chemistry of indolactam-V and its analogues. Agric. Biol. Chem. 1989, 53, 2257-2260.
    • (1989) Agric. Biol. Chem. , vol.53 , pp. 2257-2260
    • Matsuda, T.1    Nakatsuka, S.2    Goto, T.3
  • 9
    • 0024385656 scopus 로고
    • Synthesis and biological studies of simplified analogues of lyngbyatoxin A: Use of an isoxazoline-based indole synthesis. Quest for protein kinase C modulators
    • (c) Kozikowski, A. P.; Sato, K.; Basu, A.; Lazo, J. S. Synthesis and biological studies of simplified analogues of lyngbyatoxin A: use of an isoxazoline-based indole synthesis. Quest for protein kinase C modulators. J. Am. Chem. Soc. 1989, 111, 6228-6234. 111,
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 6228-6234
    • Kozikowski, A.P.1    Sato, K.2    Basu, A.3    Lazo, J.S.4
  • 10
    • 0025150557 scopus 로고
    • A regio- And stereocontrolled total synthesis of (-)-indolactam-V
    • Kogan, T. P.; Somers, T. C.; Venuti, M. C. A regio- and stereocontrolled total synthesis of (-)-indolactam-V. Tetrahedron 1990, 46, 6623-6632.
    • (1990) Tetrahedron , vol.46 , pp. 6623-6632
    • Kogan, T.P.1    Somers, T.C.2    Venuti, M.C.3
  • 11
    • 0001458546 scopus 로고
    • Synthesis, molecular modeling, 2-D-NMR, and biological evaluation of IL-V mimics as potential modulators of protein kinase C
    • (e) Kozikowski, A. P.; Ma, D.; Pang, Y.-P.; Shum, P.; Likic, V.; Mishra, P. K.; Macura, S.; Basu, A.; Lazo, J. S.; Ball, R. G. Synthesis, molecular modeling, 2-D-NMR, and biological evaluation of IL-V mimics as potential modulators of protein kinase C. J. Am. Chem. Soc. 1993, 115, 3957-3965.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 3957-3965
    • Kozikowski, A.P.1    Ma, D.2    Pang, Y.-P.3    Shum, P.4    Likic, V.5    Mishra, P.K.6    Macura, S.7    Basu, A.8    Lazo, J.S.9    Ball, R.G.10
  • 12
    • 0000100105 scopus 로고
    • Tumor promoters exist in two conformational states in solution. Stereochemistry of indolactam-V
    • (a) Endo, Y.; Hasegawa, M.; Itai, A.; Shudo, K.; Tori, M.; Asakawa, Y.; Sakai, S.-I. Tumor promoters exist in two conformational states in solution. Stereochemistry of indolactam-V. Tetrahedron Lett. 1985, 26, 1069-1072.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 1069-1072
    • Endo, Y.1    Hasegawa, M.2    Itai, A.3    Shudo, K.4    Tori, M.5    Asakawa, Y.6    Sakai, S.-I.7
  • 13
    • 0000052202 scopus 로고
    • Synthesis and stereochemistry of indolactam-V, an active fragment of teleocidins. Structural requirement for tumor-promoting activity
    • (b) Endo, Y.; Shudo, K.; Itai, A.; Hasegawa, M.; Sakai, S. Synthesis and stereochemistry of indolactam-V, an active fragment of teleocidins. Structural requirement for tumor-promoting activity. Tetrahedron 1986, 42, 5905-5924.
    • (1986) Tetrahedron , vol.42 , pp. 5905-5924
    • Endo, Y.1    Shudo, K.2    Itai, A.3    Hasegawa, M.4    Sakai, S.5
  • 15
    • 0000018373 scopus 로고
    • Computer-assisted molecular modeling of tumor promoters. Rationale for the activity of phorbol ester, teleocidin B, and aplysiatoxin
    • (b) Also see: Jeffrey, A. M.; Liskamp, R. M. Computer-assisted molecular modeling of tumor promoters. Rationale for the activity of phorbol ester, teleocidin B, and aplysiatoxin. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 241-245. Wender, P. A.; Koehler, K. F.; Sharkey, N. A.; Dell' Aquila, M. L.; Blumberg, P. M. Analysis of the phorbol ester pharmacophore on protein kinase C as a guide to the rational design of new classes of analogues. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 4214-4218. Nakamura, H.; Kishi, Y.; Pajares, M. A.; Rando, R. R. Structural basis of protein kinase C activation by tumor promoters. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 9672-9676.
    • (1986) Proc. Natl. Acad. Sci. U.S.A. , vol.83 , pp. 241-245
    • Jeffrey, A.M.1    Liskamp, R.M.2
  • 16
    • 0000370784 scopus 로고
    • Analysis of the phorbol ester pharmacophore on protein kinase C as a guide to the rational design of new classes of analogues
    • (b) Also see: Jeffrey, A. M.; Liskamp, R. M. Computer-assisted molecular modeling of tumor promoters. Rationale for the activity of phorbol ester, teleocidin B, and aplysiatoxin. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 241-245. Wender, P. A.; Koehler, K. F.; Sharkey, N. A.; Dell' Aquila, M. L.; Blumberg, P. M. Analysis of the phorbol ester pharmacophore on protein kinase C as a guide to the rational design of new classes of analogues. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 4214-4218. Nakamura, H.; Kishi, Y.; Pajares, M. A.; Rando, R. R. Structural basis of protein kinase C activation by tumor promoters. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 9672-9676.
    • (1986) Proc. Natl. Acad. Sci. U.S.A. , vol.83 , pp. 4214-4218
    • Wender, P.A.1    Koehler, K.F.2    Sharkey, N.A.3    Dell' Aquila, M.L.4    Blumberg, P.M.5
  • 17
    • 0024819506 scopus 로고
    • Structural basis of protein kinase C activation by tumor promoters
    • (b) Also see: Jeffrey, A. M.; Liskamp, R. M. Computer-assisted molecular modeling of tumor promoters. Rationale for the activity of phorbol ester, teleocidin B, and aplysiatoxin. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 241-245. Wender, P. A.; Koehler, K. F.; Sharkey, N. A.; Dell' Aquila, M. L.; Blumberg, P. M. Analysis of the phorbol ester pharmacophore on protein kinase C as a guide to the rational design of new classes of analogues. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 4214-4218. Nakamura, H.; Kishi, Y.; Pajares, M. A.; Rando, R. R. Structural basis of protein kinase C activation by tumor promoters. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 9672-9676.
    • (1989) Proc. Natl. Acad. Sci. U.S.A. , vol.86 , pp. 9672-9676
    • Nakamura, H.1    Kishi, Y.2    Pajares, M.A.3    Rando, R.R.4
  • 18
    • 0023252252 scopus 로고
    • Synthesis and stereochemistry of indolactam congeners. Conformational behavior of the nine-membered lactams
    • (a) Endo, Y.; Hasegawa, M.; Itai, A.; Shudo, K. Synthesis and stereochemistry of indolactam congeners. Conformational behavior of the nine-membered lactams. Tetrahedron 1987, 43, 3695-3704.
    • (1987) Tetrahedron , vol.43 , pp. 3695-3704
    • Endo, Y.1    Hasegawa, M.2    Itai, A.3    Shudo, K.4
  • 21
    • 0026720931 scopus 로고
    • Active conformation of a tumor promoter, teleocidin. A molecular dynamic study
    • (a) Kawai, T.; Ichinose, T.; Endo, Y.; Shudo, K.; Itai, A. Active conformation of a tumor promoter, teleocidin. A molecular dynamic study. J. Med. Chem. 1992, 25, 2248-2253.
    • (1992) J. Med. Chem. , vol.25 , pp. 2248-2253
    • Kawai, T.1    Ichinose, T.2    Endo, Y.3    Shudo, K.4    Itai, A.5
  • 23
    • 0027145039 scopus 로고
    • Designed molecules reproducing the two conformations of teleocidins
    • (a) Ohno, M.; Endo, Y.; Hirano, M.; Itai, A.; Shudo, K. Designed molecules reproducing the two conformations of teleocidins. Tetrahedron Lett. 1993, 34, 8119-8122.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 8119-8122
    • Ohno, M.1    Endo, Y.2    Hirano, M.3    Itai, A.4    Shudo, K.5
  • 24
    • 0028353679 scopus 로고
    • Chiral requirement for the tumor promoters. Conformation and activity study of benzolactams
    • (b) Endo, Y.; Ohno, M.; Hirano, M.; Takeda, M.; Itai, A.; Shudo, K. Chiral requirement for the tumor promoters. Conformation and activity study of benzolactams. BioMed. Chem. Lett. 1994, 4, 491-494.
    • (1994) BioMed. Chem. Lett. , vol.4 , pp. 491-494
    • Endo, Y.1    Ohno, M.2    Hirano, M.3    Takeda, M.4    Itai, A.5    Shudo, K.6
  • 25
    • 0030011941 scopus 로고    scopus 로고
    • Synthesis, conformation, and biological activity of teleocidin mimics, benzolactams. A clarification of the conformational flexibility problem in structure-activity studies of teleocidins
    • (c) Endo, Y.; Ohno, M.; Hirano, M.; Itai, A.; Shudo, K. Synthesis, conformation, and biological activity of teleocidin mimics, benzolactams. A clarification of the conformational flexibility problem in structure-activity studies of teleocidins. J. Am. Chem. Soc. 1996, 118, 1841-1855.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 1841-1855
    • Endo, Y.1    Ohno, M.2    Hirano, M.3    Itai, A.4    Shudo, K.5
  • 26
    • 84920296063 scopus 로고    scopus 로고
    • Personal communication. The same amounts (5.5 nmol/application) of (-)-BL-V8-310 and teleocidin B-4 induced tumors on mouse skin initiated with 7,12-dimethylbenz[a]-anthracene (DMBA) in 13.3% and 86.7%, respectively, of tumorbearing mice in week 20
    • Fujiki, H. Personal communication. The same amounts (5.5 nmol/application) of (-)-BL-V8-310 and teleocidin B-4 induced tumors on mouse skin initiated with 7,12-dimethylbenz[a]-anthracene (DMBA) in 13.3% and 86.7%, respectively, of tumorbearing mice in week 20.
    • Fujiki, H.1
  • 27
    • 0028258724 scopus 로고
    • Synthesis and biological activities of fluorine-substituted (-)-indolactam-V, the core structure of tumor promter teleocidins
    • (a) Okuno, S.; Irie, K.; Suzuki, Y.; Koshimizu, K.; Nishino, H.; Iwashima, A. Synthesis and biological activities of fluorine-substituted (-)-indolactam-V, the core structure of tumor promter teleocidins. BioMed. Chem. Lett. 1994, 4, 431-434.
    • (1994) BioMed. Chem. Lett. , vol.4 , pp. 431-434
    • Okuno, S.1    Irie, K.2    Suzuki, Y.3    Koshimizu, K.4    Nishino, H.5    Iwashima, A.6
  • 28
    • 10544240767 scopus 로고    scopus 로고
    • Synthesis and biological activities of new conformationally restricted analogues of (-)-indolactam-V: Elucidation of the biologically active conformation of the tumor-promoting teleocidins
    • (b) Irie, K.; Isaka, T.; Iwata, Y.; Yanai, Y.; Nakamura, Y.; Koizumi, F.; Ohigashi, H.; Wender, P. A.; Satomi, Y.; Nishino, H. Synthesis and biological activities of new conformationally restricted analogues of (-)-indolactam-V: elucidation of the biologically active conformation of the tumor-promoting teleocidins. J. Am. Chem. Soc. 1996, 118, 10733-10743.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 10733-10743
    • Irie, K.1    Isaka, T.2    Iwata, Y.3    Yanai, Y.4    Nakamura, Y.5    Koizumi, F.6    Ohigashi, H.7    Wender, P.A.8    Satomi, Y.9    Nishino, H.10
  • 29
    • 0028979464 scopus 로고
    • Crystal structure of the Cys2 activator-binding domain of protein kinase Cδ in complex with phorbol ester
    • Zhang, G.; Kazanietz, M. G.; Blumberg, P. M.; Hurley, J. H. Crystal structure of the Cys2 activator-binding domain of protein kinase Cδ in complex with phorbol ester. Cell 1995, 81, 917-924.
    • (1995) Cell , vol.81 , pp. 917-924
    • Zhang, G.1    Kazanietz, M.G.2    Blumberg, P.M.3    Hurley, J.H.4
  • 30
    • 0030951739 scopus 로고    scopus 로고
    • Advanced computational docking of two teleocidin congeners to Cys2 domain of protein kinase Cδ
    • Apart of this work has been reported in preliminary form: Itai, A.; Matsuo, A.; Mizutani, M.; Tomioka, N.; Sitaka, M.; Endo, Y.; Shudo, K. Advanced computational docking of two teleocidin congeners to Cys2 domain of protein kinase Cδ. Chem. Pharm. Bull. 1997, 45, 573-575.
    • (1997) Chem. Pharm. Bull. , vol.45 , pp. 573-575
    • Itai, A.1    Matsuo, A.2    Mizutani, M.3    Tomioka, N.4    Sitaka, M.5    Endo, Y.6    Shudo, K.7
  • 31
    • 0030891965 scopus 로고    scopus 로고
    • Role of hydrophobic moiety of tumor promoters. Synthesis and activity of benzolactams with alkyl substituents at various positions
    • A part of this work has been reported in a preliminary form. Endo, Y.; Ohno, M.; Takehana, S.; Driedger, P. E.; Stabel, S.; Shudo, K. Role of hydrophobic moiety of tumor promoters. Synthesis and activity of benzolactams with alkyl substituents at various positions. Chem. Pharm. Bull. 1997, 45, 424-426.
    • (1997) Chem. Pharm. Bull. , vol.45 , pp. 424-426
    • Endo, Y.1    Ohno, M.2    Takehana, S.3    Driedger, P.E.4    Stabel, S.5    Shudo, K.6
  • 32
    • 0021751909 scopus 로고
    • Structure-activity studies on synthetic analogues (indolactams) of the tumor promoter teleocidin
    • Fujiki, H.; Suganuma, M.; Nakayasu, M.; Tahira, T.; Endo, Y.; Shudo, K. Structure-activity studies on synthetic analogues (indolactams) of the tumor promoter teleocidin. Jpn. J. Cancer Res. (Gann) 1984, 75, 866-870.
    • (1984) Jpn. J. Cancer Res. (Gann) , vol.75 , pp. 866-870
    • Fujiki, H.1    Suganuma, M.2    Nakayasu, M.3    Tahira, T.4    Endo, Y.5    Shudo, K.6
  • 34
    • 0013492862 scopus 로고
    • Substitution reaction on the indole ring of (-)-indolactam-V, the fundamental structure of teleocidins
    • (a) Irie, K.; Hayashi, H.; Arai, M.; Koshimizu, K. Substitution reaction on the indole ring of (-)-indolactam-V, the fundamental structure of teleocidins. Agric. Biol. Chem. 1986, 50, 2679-2680.
    • (1986) Agric. Biol. Chem. , vol.50 , pp. 2679-2680
    • Irie, K.1    Hayashi, H.2    Arai, M.3    Koshimizu, K.4
  • 35
    • 0001546929 scopus 로고
    • Synthesis of 7-substituted indolactam-V. An introduction of hydrophobic moieties on the indole ring
    • (b) Endo, Y.; Sato, Y.; Shudo, K. Synthesis of 7-substituted indolactam-V. An introduction of hydrophobic moieties on the indole ring. Tetrahedron Lett. 1987, 43, 2241-2247.
    • (1987) Tetrahedron Lett. , vol.43 , pp. 2241-2247
    • Endo, Y.1    Sato, Y.2    Shudo, K.3
  • 36
    • 0023274535 scopus 로고
    • Structure-activity studies of the indole alkaloid tumor promoter teleocidins
    • (c) Irie, K.; Hagiwara, N.; Tokuda, H.; Koshimizu, K. Structure-activity studies of the indole alkaloid tumor promoter teleocidins. Carcinogenesis 1987, 8, 547-552.
    • (1987) Carcinogenesis , vol.8 , pp. 547-552
    • Irie, K.1    Hagiwara, N.2    Tokuda, H.3    Koshimizu, K.4
  • 37
    • 0022341259 scopus 로고
    • Activation of protein kinase C by Triton X-100 mixed micelles containing diacylgycerol and phosphatidylserine
    • Hannun, Y.; Loomis, C.; Bell, R. Activation of protein kinase C by Triton X-100 mixed micelles containing diacylgycerol and phosphatidylserine. J. Biol. Chem. 1985, 260, 10039-10043. Newton, A. C.; Koshland, D. E. High cooperativity, specificity, and multiplicity in the protein kinase C-lipid interaction. J. Biol. Chem. 1989, 264, 14909-14915. Newton, A. C.; Koshland, D. E. Phosphatidylserine affects specificity of protein kinase C substrate phosphorylation and autophosphorylation. Biochemistry 1990, 29, 6656-6661. Bazzi, M. D.; Nelsestuen, G. L. Highly sequential binding of protein kinase C and related proteins to membranes. Biochemistry 1991, 30, 7970-7977.
    • (1985) J. Biol. Chem. , vol.260 , pp. 10039-10043
    • Hannun, Y.1    Loomis, C.2    Bell, R.3
  • 38
    • 0024450585 scopus 로고
    • High cooperativity, specificity, and multiplicity in the protein kinase C-lipid interaction
    • Hannun, Y.; Loomis, C.; Bell, R. Activation of protein kinase C by Triton X-100 mixed micelles containing diacylgycerol and phosphatidylserine. J. Biol. Chem. 1985, 260, 10039-10043. Newton, A. C.; Koshland, D. E. High cooperativity, specificity, and multiplicity in the protein kinase C-lipid interaction. J. Biol. Chem. 1989, 264, 14909-14915. Newton, A. C.; Koshland, D. E. Phosphatidylserine affects specificity of protein kinase C substrate phosphorylation and autophosphorylation. Biochemistry 1990, 29, 6656-6661. Bazzi, M. D.; Nelsestuen, G. L. Highly sequential binding of protein kinase C and related proteins to membranes. Biochemistry 1991, 30, 7970-7977.
    • (1989) J. Biol. Chem. , vol.264 , pp. 14909-14915
    • Newton, A.C.1    Koshland, D.E.2
  • 39
    • 0025340672 scopus 로고
    • Phosphatidylserine affects specificity of protein kinase C substrate phosphorylation and autophosphorylation
    • Hannun, Y.; Loomis, C.; Bell, R. Activation of protein kinase C by Triton X-100 mixed micelles containing diacylgycerol and phosphatidylserine. J. Biol. Chem. 1985, 260, 10039-10043. Newton, A. C.; Koshland, D. E. High cooperativity, specificity, and multiplicity in the protein kinase C-lipid interaction. J. Biol. Chem. 1989, 264, 14909-14915. Newton, A. C.; Koshland, D. E. Phosphatidylserine affects specificity of protein kinase C substrate phosphorylation and autophosphorylation. Biochemistry 1990, 29, 6656-6661. Bazzi, M. D.; Nelsestuen, G. L. Highly sequential binding of protein kinase C and related proteins to membranes. Biochemistry 1991, 30, 7970-7977.
    • (1990) Biochemistry , vol.29 , pp. 6656-6661
    • Newton, A.C.1    Koshland, D.E.2
  • 40
    • 0025912944 scopus 로고
    • Highly sequential binding of protein kinase C and related proteins to membranes
    • Hannun, Y.; Loomis, C.; Bell, R. Activation of protein kinase C by Triton X-100 mixed micelles containing diacylgycerol and phosphatidylserine. J. Biol. Chem. 1985, 260, 10039-10043. Newton, A. C.; Koshland, D. E. High cooperativity, specificity, and multiplicity in the protein kinase C-lipid interaction. J. Biol. Chem. 1989, 264, 14909-14915. Newton, A. C.; Koshland, D. E. Phosphatidylserine affects specificity of protein kinase C substrate phosphorylation and autophosphorylation. Biochemistry 1990, 29, 6656-6661. Bazzi, M. D.; Nelsestuen, G. L. Highly sequential binding of protein kinase C and related proteins to membranes. Biochemistry 1991, 30, 7970-7977.
    • (1991) Biochemistry , vol.30 , pp. 7970-7977
    • Bazzi, M.D.1    Nelsestuen, G.L.2
  • 41
    • 0029974959 scopus 로고    scopus 로고
    • Role of hydrophobic moiety of tumor promoters. Synthesis and activity of 9-alkylated benzolactams
    • Endo, Y.; Yamaguchi, M.; Hirano, M.; Shudo, K. Role of hydrophobic moiety of tumor promoters. Synthesis and activity of 9-alkylated benzolactams. Chem. Pharm. Bull. 1996, 44, 1138-1140.
    • (1996) Chem. Pharm. Bull. , vol.44 , pp. 1138-1140
    • Endo, Y.1    Yamaguchi, M.2    Hirano, M.3    Shudo, K.4
  • 42
    • 0000372552 scopus 로고
    • Synthesis of the enantiomers of 5-hexa- Decanolide, the pheromone of the queen of the oriental hornet, Vespa orientalis, employing enzymic resolution of 2-aminodecanoic acid as the keystep
    • Mon, K.; Ohtsuka, T. Synthesis of the enantiomers of 5-hexa- decanolide, the pheromone of the queen of the oriental hornet, Vespa orientalis, employing enzymic resolution of 2-aminodecanoic acid as the keystep. Tetrahedron Lett. 1985, 41, 547-551.
    • (1985) Tetrahedron Lett. , vol.41 , pp. 547-551
    • Mon, K.1    Ohtsuka, T.2
  • 43
    • 0018613826 scopus 로고
    • A possible naturally occurring tumor promoter, teleocidin B from Streptomyces
    • Fujiki, H.; Mon, M.; Nakayasu, M.; Terada, M.; Sugimura, T. A possible naturally occurring tumor promoter, teleocidin B from Streptomyces. Biochem. Biophys. Res. Commun. 1979, 90, 976-983. Hubermann, E.; Callaham, M. F. Induction of terminal differentiation in human promyelocytic leukemia cells by tumor-promoting agents. Proc. Natl. Acad. Sci. U.S.A. 1979, 76,1293-1297.
    • (1979) Biochem. Biophys. Res. Commun. , vol.90 , pp. 976-983
    • Fujiki, H.1    Mon, M.2    Nakayasu, M.3    Terada, M.4    Sugimura, T.5
  • 44
    • 2642682843 scopus 로고
    • Induction of terminal differentiation in human promyelocytic leukemia cells by tumor-promoting agents
    • Fujiki, H.; Mon, M.; Nakayasu, M.; Terada, M.; Sugimura, T. A possible naturally occurring tumor promoter, teleocidin B from Streptomyces. Biochem. Biophys. Res. Commun. 1979, 90, 976-983. Hubermann, E.; Callaham, M. F. Induction of terminal differentiation in human promyelocytic leukemia cells by tumor-promoting agents. Proc. Natl. Acad. Sci. U.S.A. 1979, 76,1293-1297.
    • (1979) Proc. Natl. Acad. Sci. U.S.A. , vol.76 , pp. 1293-1297
    • Hubermann, E.1    Callaham, M.F.2
  • 45
    • 0010708038 scopus 로고
    • Specific binding of phorbol ester tumor promoters
    • Driedger, P. E.; Blumberg, P. M. Specific binding of phorbol ester tumor promoters. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 567-571. Driedger, P. E.; Stabel, S.; Frith, D.: Horgan, T. J. Mezerein and 12-deoxyphorboI 13-isobutyrate, protein kinase C ligands with differential biological activities, do not distinguish PKC-isotypes α, β1, β2 and γ. Receptors Channels 1994, 2, 99-106.
    • (1980) Proc. Natl. Acad. Sci. U.S.A. , vol.77 , pp. 567-571
    • Driedger, P.E.1    Blumberg, P.M.2
  • 46
    • 0028038032 scopus 로고
    • Mezerein and 12-deoxyphorboI 13-isobutyrate, protein kinase C ligands with differential biological activities, do not distinguish PKC-isotypes α, β1, β2 and γ
    • Driedger, P. E.; Blumberg, P. M. Specific binding of phorbol ester tumor promoters. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 567-571. Driedger, P. E.; Stabel, S.; Frith, D.: Horgan, T. J. Mezerein and 12-deoxyphorboI 13-isobutyrate, protein kinase C ligands with differential biological activities, do not distinguish PKC-isotypes α, β1, β2 and γ. Receptors Channels 1994, 2, 99-106.
    • (1994) Receptors Channels , vol.2 , pp. 99-106
    • Driedger, P.E.1    Stabel, S.2    Frith, D.3    Horgan, T.J.4
  • 47
    • 0025780455 scopus 로고
    • Synthesis of tetramethyl analogue of teleocidin
    • Webb, R. R., II; Venuti, M. C.; Eigenbrot, C. Synthesis of tetramethyl analogue of teleocidin. J. Org. Chem. 1991, 56, 4706-4713.
    • (1991) J. Org. Chem. , vol.56 , pp. 4706-4713
    • Webb II, R.R.1    Venuti, M.C.2    Eigenbrot, C.3
  • 48
    • 0027985242 scopus 로고
    • Rational automatic search method for stable docking models of protein and ligand
    • Mizutani, M. Y.; Tomioka, N.; Itai, A. Rational automatic search method for stable docking models of protein and ligand. J. Mol. Biol. 1994, 243, 310-326.
    • (1994) J. Mol. Biol. , vol.243 , pp. 310-326
    • Mizutani, M.Y.1    Tomioka, N.2    Itai, A.3
  • 49
    • 0028491136 scopus 로고
    • GREEN: A program package for docking studies in rational drug design
    • Tomioka, N.; Itai, A. GREEN: A program package for docking studies in rational drug design. J. Comput.-Aided Mol. Des. 1994, 8, 347-366.
    • (1994) J. Comput.-Aided Mol. Des. , vol.8 , pp. 347-366
    • Tomioka, N.1    Itai, A.2
  • 51
    • 15444345629 scopus 로고    scopus 로고
    • Modeling, chemistry, and biology of the benzolactam analogues of indolactam V (ILV). 2. Identification of the binding site of the benzolactams in the CRD2 activator-binding domain of PKCδ and discovery of an analogue of improved isozyme selectivity
    • Kozikowski, A. P.; Wang, S.; Ma, D.; Yao, J.; Ahmad, S.; Glazer, R. I.; Bogi, K.; Acs, P.; Modarres, S.; Lewin, N. E.; Blurnberg, P. M. Modeling, chemistry, and biology of the benzolactam analogues of indolactam V (ILV). 2. Identification of the binding site of the benzolactams in the CRD2 activator-binding domain of PKCδ and discovery of an analogue of improved isozyme selectivity. J. Med. Chem. 1997, 40, 1316-1326.
    • (1997) J. Med. Chem. , vol.40 , pp. 1316-1326
    • Kozikowski, A.P.1    Wang, S.2    Ma, D.3    Yao, J.4    Ahmad, S.5    Glazer, R.I.6    Bogi, K.7    Acs, P.8    Modarres, S.9    Lewin, N.E.10    Blurnberg, P.M.11
  • 52
    • 84920296062 scopus 로고    scopus 로고
    • note
    • From the decomposition analysis of interaction energies of 3 and 4, relative stability of 3 compared to 4 is attributed nearly equally to van der Waals and electrostatic energies. It is likely that, in 3, a larger indole ring contributes to favorable van der Waals interaction and the 1-NH group of 3 contributes to favorable electrostatic interaction.
  • 56
    • 0000325856 scopus 로고
    • Silane reduction in acidic media. II. Reduction of aryl aldehydes and ketones by trialkylsilanes in trifluoroacetic acid. A selective method for converting the carbonyl group to methylene
    • West, C. T.; Donnelly, S. J.; Kooistra, D. A.; Doyle, M. P. Silane reduction in acidic media. II. Reduction of aryl aldehydes and ketones by trialkylsilanes in trifluoroacetic acid. A selective method for converting the carbonyl group to methylene. J. Org. Chem. 1973, 38, 2675-2681.
    • (1973) J. Org. Chem. , vol.38 , pp. 2675-2681
    • West, C.T.1    Donnelly, S.J.2    Kooistra, D.A.3    Doyle, M.P.4
  • 57
    • 0025269877 scopus 로고
    • Reactions of 2-phenylethyl and 3-phenylpropyl carbinols with fluorosulfuric acid
    • Bright, S. T.; Coxon, J. M.; Steel, P. J. Reactions of 2-phenylethyl and 3-phenylpropyl carbinols with fluorosulfuric acid. J. Org. Chem. 1990, 55, 1338-1344.
    • (1990) J. Org. Chem. , vol.55 , pp. 1338-1344
    • Bright, S.T.1    Coxon, J.M.2    Steel, P.J.3
  • 58
    • 0000299709 scopus 로고
    • Chromic acid oxidation of indans and tetraline to 1-indanones and 1-tetralones using Jones and other Cr (VI) reagents
    • Rangarajan, R.; Eisenbraun, E. J. Chromic acid oxidation of indans and tetraline to 1-indanones and 1-tetralones using Jones and other Cr (VI) reagents. J. Org. Chem. 1985, 50, 2435-2438.
    • (1985) J. Org. Chem. , vol.50 , pp. 2435-2438
    • Rangarajan, R.1    Eisenbraun, E.J.2
  • 60
    • 0342741010 scopus 로고
    • The X-ray structure determination of dihydroteleocidin B monobromoacetate
    • Harada, H.; Sakabe, N.; Hirata, Y.; Tomiie, Y.; Nitta, I. The X-ray structure determination of dihydroteleocidin B monobromoacetate. Bull. Chem. Soc. Jpn. 1966, 39, 1773-1774. Sakai, S.-I.; Aimi, N.; Yamaguchi, K.; Hitotsuyanagi, Y.; Watanabe, C.; Yokose, K.; Koyama, Y.; Shudo, K.; Itai, A. Elucidation of the structure of olivoretin A and D (teleocidin B). Chem. Pharm. Bull. 1984, 32, 354-357.
    • (1966) Bull. Chem. Soc. Jpn. , vol.39 , pp. 1773-1774
    • Harada, H.1    Sakabe, N.2    Hirata, Y.3    Tomiie, Y.4    Nitta, I.5
  • 61
    • 84998292328 scopus 로고
    • Elucidation of the structure of olivoretin A and D (teleocidin B)
    • Harada, H.; Sakabe, N.; Hirata, Y.; Tomiie, Y.; Nitta, I. The X-ray structure determination of dihydroteleocidin B monobromoacetate. Bull. Chem. Soc. Jpn. 1966, 39, 1773-1774. Sakai, S.-I.; Aimi, N.; Yamaguchi, K.; Hitotsuyanagi, Y.; Watanabe, C.; Yokose, K.; Koyama, Y.; Shudo, K.; Itai, A. Elucidation of the structure of olivoretin A and D (teleocidin B). Chem. Pharm. Bull. 1984, 32, 354-357.
    • (1984) Chem. Pharm. Bull. , vol.32 , pp. 354-357
    • Sakai, S.-I.1    Aimi, N.2    Yamaguchi, K.3    Hitotsuyanagi, Y.4    Watanabe, C.5    Yokose, K.6    Koyama, Y.7    Shudo, K.8    Itai, A.9
  • 62
    • 0025390935 scopus 로고
    • MOPAC: A semiempirical molecular orbital program
    • Stewart, J. J. P. MOPAC: A semiempirical molecular orbital program. J. Comput.-Aided Mol. Des. 1990, 4, 1-105.
    • (1990) J. Comput.-Aided Mol. Des. , vol.4 , pp. 1-105
    • Stewart, J.J.P.1


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