메뉴 건너뛰기




Volumn 49, Issue 11, 2006, Pages 3185-3203

Conformationally constrained analogues of diacylglycerol. 26. Exploring the chemical space surrounding the C1 domain of protein kinase C with DAG-lactones containing aryl groups at the sn-1 and sn-2 positions

Author keywords

[No Author keywords available]

Indexed keywords

DIACYLGLYCEROL; DIACYLGLYCEROL LACTONE; PHENYL GROUP; PROTEIN KINASE C; UNCLASSIFIED DRUG;

EID: 33744817634     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060011o     Document Type: Article
Times cited : (11)

References (45)
  • 1
    • 0032104245 scopus 로고    scopus 로고
    • The extended protein kinase C superfamily
    • Mellor, H.; Parker, P. J. The extended protein kinase C superfamily. Biochem. J. 1998, 332, 281-292.
    • (1998) Biochem. J. , vol.332 , pp. 281-292
    • Mellor, H.1    Parker, P.J.2
  • 3
    • 0033989653 scopus 로고    scopus 로고
    • The role of protein kinase C in the regulation of cell growth and in signalling to the cell nucleus
    • Buchner, K. The role of protein kinase C in the regulation of cell growth and in signalling to the cell nucleus. J. Cancer Res. Clin. Oncol 2000, 126, 1-11.
    • (2000) J. Cancer Res. Clin. Oncol , vol.126 , pp. 1-11
    • Buchner, K.1
  • 5
    • 0034025493 scopus 로고    scopus 로고
    • Eyes wide shut: Protein kinase C isozymes are not the only receptors for the phorbol ester tumor promoters
    • Kazanietz, M. G. Eyes wide shut: Protein kinase C isozymes are not the only receptors for the phorbol ester tumor promoters. Mol. Carcinog. 2000, 28, 5-11.
    • (2000) Mol. Carcinog. , vol.28 , pp. 5-11
    • Kazanietz, M.G.1
  • 6
    • 0036209077 scopus 로고    scopus 로고
    • Novel "nonkinase" phorbol ester receptors: The Cl domain connection
    • Kazanietz, M. G. Novel "nonkinase" phorbol ester receptors: The Cl domain connection. Mol. Pharmacol. 2002, 61, 759-767;
    • (2002) Mol. Pharmacol. , vol.61 , pp. 759-767
    • Kazanietz, M.G.1
  • 7
    • 0036239376 scopus 로고    scopus 로고
    • Erratum
    • Erratum. Mol. Pharmacol. 2002, 61, 1265.
    • (2002) Mol. Pharmacol. , vol.61 , pp. 1265
  • 8
    • 0036905264 scopus 로고    scopus 로고
    • Move over protein kinase C, you've got company: Alternative cellular effectors of diacylglycerol and phorbol esters
    • Brose, N.; Rosenmund, C. Move over protein kinase C, you've got company: Alternative cellular effectors of diacylglycerol and phorbol esters. J. Cell Sci. 2002, 115, 4399-4411.
    • (2002) J. Cell Sci. , vol.115 , pp. 4399-4411
    • Brose, N.1    Rosenmund, C.2
  • 9
    • 4444245423 scopus 로고    scopus 로고
    • Protein kinase C and beyond
    • Spitaler. M.; Cantrell, D. A. Protein kinase C and beyond. Nat. Immunol. 2004, 5, 785-790.
    • (2004) Nat. Immunol. , vol.5 , pp. 785-790
    • Spitaler, M.1    Cantrell, D.A.2
  • 10
    • 0347986633 scopus 로고    scopus 로고
    • Emerging and diverse roles of protein kinase C in immune cell signalling
    • Tan, S. L.; Parker, P. J. Emerging and diverse roles of protein kinase C in immune cell signalling. Biochem. J. 2003, 376, 545-552.
    • (2003) Biochem. J. , vol.376 , pp. 545-552
    • Tan, S.L.1    Parker, P.J.2
  • 11
    • 1942453351 scopus 로고    scopus 로고
    • Diacylglycerol's affair with protein kinase C turns 25
    • Newton, A. C. Diacylglycerol's affair with protein kinase C turns 25. Trends Pharmacol. Sci. 2004, 25, 175-177.
    • (2004) Trends Pharmacol. Sci. , vol.25 , pp. 175-177
    • Newton, A.C.1
  • 12
    • 0035413601 scopus 로고    scopus 로고
    • Protein kinase C: Structural and spatial regulation by phosphorylation, cofactors, and macromolecular interactions
    • Newton, A. C. Protein kinase C: Structural and spatial regulation by phosphorylation, cofactors, and macromolecular interactions. Chem. Rev. 2001, 101, 2353-2364.
    • (2001) Chem. Rev. , vol.101 , pp. 2353-2364
    • Newton, A.C.1
  • 13
    • 0036789740 scopus 로고    scopus 로고
    • Protein kinase C isoforms and lipid second messengers: A critical nuclear partnership?
    • Neri, L. M.; Borgatti, P.; Capitani, S.; Martelli, A. M. Protein kinase C isoforms and lipid second messengers: a critical nuclear partnership? Histol. Histopathol. 2002, 17, 1311-1316.
    • (2002) Histol. Histopathol. , vol.17 , pp. 1311-1316
    • Neri, L.M.1    Borgatti, P.2    Capitani, S.3    Martelli, A.M.4
  • 16
    • 0038679456 scopus 로고    scopus 로고
    • Synthetic diacylglycerols (DAG) and DAG-lactones as activators of protein kinase C (PK-C)
    • Marquez, V. E.; Blumberg, P. M. Synthetic diacylglycerols (DAG) and DAG-lactones as activators of protein kinase C (PK-C). Ace. Chem. Res. 2003, 36, 434-443.
    • (2003) Ace. Chem. Res. , vol.36 , pp. 434-443
    • Marquez, V.E.1    Blumberg, P.M.2
  • 17
    • 2542540617 scopus 로고    scopus 로고
    • Confbrmationally constrained analogues of diacylglycerol. 21. A solid-phase method of synthesis of diacylglycerol lactones as a prelude to a combinatorial approach for the synthesis of protein kinase C isozyme-specific ligands
    • Duan, D. H.; Lewin, N. E.; Sigano, D. M.; Blumberg, P. M.; Marquez, V. E. Confbrmationally constrained analogues of diacylglycerol. 21. A solid-phase method of synthesis of diacylglycerol lactones as a prelude to a combinatorial approach for the synthesis of protein kinase C isozyme-specific ligands. J. Med. Chem. 2004, 47, 3248-3254.
    • (2004) J. Med. Chem. , vol.47 , pp. 3248-3254
    • Duan, D.H.1    Lewin, N.E.2    Sigano, D.M.3    Blumberg, P.M.4    Marquez, V.E.5
  • 18
    • 0035821598 scopus 로고    scopus 로고
    • An optimized protein kinase C activating diacylglycerol combining high binding affinity (Ki) with reduced lipophilicity (log P)
    • Nacro, K.; Sigano, D. M.; Yan, S.; Nicklaus, M. C.; Pearce, L. L.; Lewin, N. E.; Garfield, S. H.; Blumberg, P. M.; Marquez, V. E. An optimized protein kinase C activating diacylglycerol combining high binding affinity (Ki) with reduced lipophilicity (log P). J. Med. Chem. 2001, 44, 1892-1904.
    • (2001) J. Med. Chem. , vol.44 , pp. 1892-1904
    • Nacro, K.1    Sigano, D.M.2    Yan, S.3    Nicklaus, M.C.4    Pearce, L.L.5    Lewin, N.E.6    Garfield, S.H.7    Blumberg, P.M.8    Marquez, V.E.9
  • 21
    • 0001509942 scopus 로고    scopus 로고
    • Prediction of physicochemical parameters by atomic contributions
    • Wildman, S. A.; Crippen, G. M. Prediction of physicochemical parameters by atomic contributions. J. Chem. Inf. Comput. Sci. 1999, 39, 868-873.
    • (1999) J. Chem. Inf. Comput. Sci. , vol.39 , pp. 868-873
    • Wildman, S.A.1    Crippen, G.M.2
  • 22
    • 1542652298 scopus 로고    scopus 로고
    • 3H]-Phorbol 12.13-dibutyrate binding assay for protein kinase C and related proteins
    • 3H]-Phorbol 12.13-dibutyrate binding assay for protein kinase C and related proteins. Methods Mol. Biol. 2003, 233, 129-156.
    • (2003) Methods Mol. Biol. , vol.233 , pp. 129-156
    • Lewin, N.E.1    Blumberg, P.M.2
  • 23
    • 31144449363 scopus 로고    scopus 로고
    • The role of protein kinase C-alpha in hematologic malignancies
    • Lahn, M.; Sundell, K.; Kohler, G. The role of protein kinase C-alpha in hematologic malignancies. Acta Haematol. 2006, 115, 1-8.
    • (2006) Acta Haematol. , vol.115 , pp. 1-8
    • Lahn, M.1    Sundell, K.2    Kohler, G.3
  • 24
    • 2442543262 scopus 로고    scopus 로고
    • The role of protein kinase C-alpha (PKC-alpha) in cancer and its modulation by the novel PKC-alpha-specific inhibitor aprinocarsen
    • Hanauske, A. R.; Sundell, K.; Lahn, M. The role of protein kinase C-alpha (PKC-alpha) in cancer and its modulation by the novel PKC-alpha-specific inhibitor aprinocarsen. Curr. Pharm. Des. 2004, 10, 1923-1936.
    • (2004) Curr. Pharm. Des. , vol.10 , pp. 1923-1936
    • Hanauske, A.R.1    Sundell, K.2    Lahn, M.3
  • 25
    • 0028979464 scopus 로고
    • Crystal-structure of the Cys2 activator-binding domain of protein-kinase C-delta in complex with phorbol ester
    • Zhang, G. G.; Kazanietz, M. G.; Blumberg, P. M.; Hurley, J. H. Crystal-structure of the Cys2 activator-binding domain of protein-kinase C-delta in complex with phorbol ester. Cell 1995, 81, 917-924.
    • (1995) Cell , vol.81 , pp. 917-924
    • Zhang, G.G.1    Kazanietz, M.G.2    Blumberg, P.M.3    Hurley, J.H.4
  • 26
    • 0034624775 scopus 로고    scopus 로고
    • Conformationally constrained analogues of diacylglycerol (DAG). 16. How much structural complexity is necessary for recognition and high binding affinity to protein kinase C?
    • Nacro, K.; Bienfait, B.; Lee, J.; Han, K. C.; Kang, J. H.; Benzaria, S.; Lewin, N. E.; Bhattacharyya, D. K.; Blumberg, P. M.; Marquez, V. E. Conformationally constrained analogues of diacylglycerol (DAG). 16. How much structural complexity is necessary for recognition and high binding affinity to protein kinase C? J. Med. Chem. 2000, 43, 921-944.
    • (2000) J. Med. Chem. , vol.43 , pp. 921-944
    • Nacro, K.1    Bienfait, B.2    Lee, J.3    Han, K.C.4    Kang, J.H.5    Benzaria, S.6    Lewin, N.E.7    Bhattacharyya, D.K.8    Blumberg, P.M.9    Marquez, V.E.10
  • 27
    • 18544378008 scopus 로고    scopus 로고
    • Diacylglycerol (DAG)-lactones, a new class of protein kinase C (PKC) agonists, induce apoptosis in LNCaP prostate cancer cells by selective activation of PKCalpha
    • Garcia-Bermejo, M. L.; Leskow, F. C.; Fujii, T.; Wang, Q.; Blumberg, P. M.; Ohba, M.; Kuroki, T.; Han, K. C.; Lee, J.; Marquez, V. E.; Kazanietz, M. G. Diacylglycerol (DAG)-lactones, a new class of protein kinase C (PKC) agonists, induce apoptosis in LNCaP prostate cancer cells by selective activation of PKCalpha. J. Biol. Chem. 2002, 277, 645-655;
    • (2002) J. Biol. Chem. , vol.277 , pp. 645-655
    • Garcia-Bermejo, M.L.1    Leskow, F.C.2    Fujii, T.3    Wang, Q.4    Blumberg, P.M.5    Ohba, M.6    Kuroki, T.7    Han, K.C.8    Lee, J.9    Marquez, V.E.10    Kazanietz, M.G.11
  • 28
    • 2542422946 scopus 로고    scopus 로고
    • Erratum
    • Erratum. J. Biol. Chem. 2004, 279, 23846.
    • (2004) J. Biol. Chem. , vol.279 , pp. 23846
  • 29
    • 0029102822 scopus 로고
    • Residues in the 2nd cysteine-rich region of protein-kinase-C-delta relevant to phorbol ester binding as revealed by site-directed mutagenesis
    • Kazanietz, M. G.; Wang, S.; Milne, G. W. A.; Lewin, N. E.; Liu, H. L.; Blumberg, P. M. Residues in the 2nd cysteine-rich region of protein-kinase-C- delta relevant to phorbol ester binding as revealed by site-directed mutagenesis. J. Biol. Chem. 1995, 270, 21852-21859.
    • (1995) J. Biol. Chem. , vol.270 , pp. 21852-21859
    • Kazanietz, M.G.1    Wang, S.2    Milne, G.W.A.3    Lewin, N.E.4    Liu, H.L.5    Blumberg, P.M.6
  • 30
    • 0029038685 scopus 로고
    • Low-affinity binding of phorbol esters to protein-kinase-C and its recombinant cysteine-rich region in the absence of phospholipids
    • Kazanietz, M. G.; Barchi, J. J.; Omichinski, J. G.; Blumberg, P. M. Low-affinity binding of phorbol esters to protein-kinase-C and its recombinant cysteine-rich region in the absence of phospholipids. J. Biol. Chem. 1995, 270, 14679-14684.
    • (1995) J. Biol. Chem. , vol.270 , pp. 14679-14684
    • Kazanietz, M.G.1    Barchi, J.J.2    Omichinski, J.G.3    Blumberg, P.M.4
  • 31
    • 0015966027 scopus 로고
    • Preparation and synthetic utility of some organotin derivatives of nucleosides
    • Wagner, D.; Verheyden, J. P. H.; Moffatt, J. G. Preparation and synthetic utility of some organotin derivatives of nucleosides. J. Org. Chem. 1974, 39, 24-30.
    • (1974) J. Org. Chem. , vol.39 , pp. 24-30
    • Wagner, D.1    Verheyden, J.P.H.2    Moffatt, J.G.3
  • 32
    • 0032130269 scopus 로고    scopus 로고
    • Design and synthesis of bioisosteres of ultrapotent protein kinase C (PKC) ligand, 5-acetoxymethyl-5-hydroxymethyl-alkylidene tetrahydro-2-furanone
    • Lee, J. Design and synthesis of bioisosteres of ultrapotent protein kinase C (PKC) ligand, 5-acetoxymethyl-5-hydroxymethyl-alkylidene tetrahydro-2-furanone. Arch. Pharm. Res. 1998, 21, 452-457.
    • (1998) Arch. Pharm. Res. , vol.21 , pp. 452-457
    • Lee, J.1
  • 33
    • 0038115296 scopus 로고    scopus 로고
    • Conformationally constrained analogues of diacylglycerol. 19. Synthesis and protein kinase C binding affinity of diacylglycerol lactones bearing an N-hydroxylamide side chain
    • Choi, Y.; Kang, J. H.; Lewin, N. E.; Blumberg, P. M.; Lee, J.; Marquez, V. E. Conformationally constrained analogues of diacylglycerol. 19. Synthesis and protein kinase C binding affinity of diacylglycerol lactones bearing an N-hydroxylamide side chain. J. Med. Chem. 2003, 46, 2790-2793.
    • (2003) J. Med. Chem. , vol.46 , pp. 2790-2793
    • Choi, Y.1    Kang, J.H.2    Lewin, N.E.3    Blumberg, P.M.4    Lee, J.5    Marquez, V.E.6
  • 34
    • 0030050588 scopus 로고    scopus 로고
    • Conformationally constrained analogues of diacylglycerol. 10. Ultrapotent protein kinase C ligands based on a racemic 5-disubstituted tetrahydro-2-furanone template
    • Sharma, R.; Lee, J.; Wang, S.; Milne, G. W.; Lewin, N. E.; Blumberg, P. M.; Marquez, V. E. Conformationally constrained analogues of diacylglycerol. 10. Ultrapotent protein kinase C ligands based on a racemic 5-disubstituted tetrahydro-2-furanone template. J. Med. Chem. 1996, 39, 19-28.
    • (1996) J. Med. Chem. , vol.39 , pp. 19-28
    • Sharma, R.1    Lee, J.2    Wang, S.3    Milne, G.W.4    Lewin, N.E.5    Blumberg, P.M.6    Marquez, V.E.7
  • 35
    • 0030032407 scopus 로고    scopus 로고
    • Conformationally constrained analogues of diacylglycerol. 11. Ultrapotent protein kinase C ligands based on a chiral 5-disubstituted tetrahydro-2- furanone template
    • Lee, J.; Wang, S.; Milne, G. W.; Sharma, R.; Lewin, N. E.; Blumberg, P. M.; Marquez, V. E. Conformationally constrained analogues of diacylglycerol. 11. Ultrapotent protein kinase C ligands based on a chiral 5-disubstituted tetrahydro-2-furanone template. J. Med. Chem. 1996, 39, 29-35.
    • (1996) J. Med. Chem. , vol.39 , pp. 29-35
    • Lee, J.1    Wang, S.2    Milne, G.W.3    Sharma, R.4    Lewin, N.E.5    Blumberg, P.M.6    Marquez, V.E.7
  • 36
    • 0030023919 scopus 로고    scopus 로고
    • Conformationally constrained analogues of diacylglycerol. 12. Ultrapotent protein kinase C ligands based on a chiral 4,4-disubstituted heptono-1,4-lactone template
    • Lee, J.; Sharma, R.; Wang, S.; Milne, G. W.; Lewin, N. E.; Szallasi, Z.; Blumberg, P. M.; George, C.; Marquez, V. E. Conformationally constrained analogues of diacylglycerol. 12. Ultrapotent protein kinase C ligands based on a chiral 4,4-disubstituted heptono-1,4-lactone template. J. Med. Chem. 1996, 39, 36-45.
    • (1996) J. Med. Chem. , vol.39 , pp. 36-45
    • Lee, J.1    Sharma, R.2    Wang, S.3    Milne, G.W.4    Lewin, N.E.5    Szallasi, Z.6    Blumberg, P.M.7    George, C.8    Marquez, V.E.9
  • 37
    • 0000758418 scopus 로고
    • Conformationally constrained analogs of diacylglycerol. Interaction of gammalactones with the phorbol ester receptor of protein-kinase-C
    • Teng, K.; Marquez, V. E.; Milne, G. W. A.; Barchi, J. J.; Kazanietz, M. G.; Lewin, N. E.; Blumberg, P. M.; Abushanab, E. Conformationally constrained analogs of diacylglycerol. Interaction of gammalactones with the phorbol ester receptor of protein-kinase-C. J. Am. Chem. Soc. 1992, 114, 1059-1070.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 1059-1070
    • Teng, K.1    Marquez, V.E.2    Milne, G.W.A.3    Barchi, J.J.4    Kazanietz, M.G.5    Lewin, N.E.6    Blumberg, P.M.7    Abushanab, E.8
  • 38
    • 33744828908 scopus 로고    scopus 로고
    • Tripos, Inc. www.tripos.com.
  • 39
    • 0037571112 scopus 로고    scopus 로고
    • Merck molecular force field. 1. Basis, form, scope, parameterization, and performance of MMFF94
    • Halgren, T. A. Merck molecular force field. 1. Basis, form, scope, parameterization, and performance of MMFF94. J. Comput. Chem. 1996, 17, 490-519.
    • (1996) J. Comput. Chem. , vol.17 , pp. 490-519
    • Halgren, T.A.1
  • 40
    • 0031552362 scopus 로고    scopus 로고
    • Development and validation of a genetic algorithm for flexible docking
    • Jones, G.; Willett, P.; Glen, R. C.; Leach, A. R.; Taylor, R. Development and validation of a genetic algorithm for flexible docking. J. Mol. Biol. 1997, 267, 727-748.
    • (1997) J. Mol. Biol. , vol.267 , pp. 727-748
    • Jones, G.1    Willett, P.2    Glen, R.C.3    Leach, A.R.4    Taylor, R.5
  • 41
    • 0035840364 scopus 로고    scopus 로고
    • The oxidation of aromatic aldehydes by magnesium monoperoxyphthalate and urea-hydrogen peroxide
    • Heaney, H.; Newbold, A. J. The oxidation of aromatic aldehydes by magnesium monoperoxyphthalate and urea-hydrogen peroxide. Tetrahedron Lett. 2001, 42, 6607-6609.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 6607-6609
    • Heaney, H.1    Newbold, A.J.2
  • 42
    • 0030975106 scopus 로고    scopus 로고
    • Total synthesis of mycobactin S, a siderophore and growth promoter of mycobacterium smegmatis, and determination of its growth inhibitory activity against Mycobacterium tuberculosis
    • Hu, J.; Miller, M. J. Total synthesis of mycobactin S, a siderophore and growth promoter of mycobacterium smegmatis, and determination of its growth inhibitory activity against Mycobacterium tuberculosis. J. Am. Chem. Soc. 1997, 119, 3462-3468.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 3462-3468
    • Hu, J.1    Miller, M.J.2
  • 43
    • 85047673915 scopus 로고
    • An efficient synthesis of m-hydroxycocaine and m-hydroxybenzoylecgonine, 2 metabolites of cocaine
    • Tamagnan, G.; Gao, Y. G.; Bakthavachalam, V.; White, W. L.; Neumeyer, J. L. An efficient synthesis of m-hydroxycocaine and m-hydroxybenzoylecgonine, 2 metabolites of cocaine. Tetrahedron Lett. 1995, 36, 5861-5864.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 5861-5864
    • Tamagnan, G.1    Gao, Y.G.2    Bakthavachalam, V.3    White, W.L.4    Neumeyer, J.L.5
  • 44
    • 0000056281 scopus 로고
    • The synthesis of (S) and (R) enantiomers of novel hydroxymethylated isodideoxynucleosides
    • Zintek, L. B.; Jeon, G. S.; Nair, V. The synthesis of (S) and (R) enantiomers of novel hydroxymethylated isodideoxynucleosides. Heterocycles 1994, 37, 1853-1864.
    • (1994) Heterocycles , vol.37 , pp. 1853-1864
    • Zintek, L.B.1    Jeon, G.S.2    Nair, V.3
  • 45
    • 84987536369 scopus 로고
    • Enantioselective microbial reduction of monoesters of 1,3-dihydroxypropanone-synthesis of (S)-1,2-O-isopropylideneglycerol and (R)-1,2-isopropylideneglycerol
    • Aragozzini, F.; Maconi, E.; Potenza, D.; Scolastico, C. Enantioselective microbial reduction of monoesters of 1,3-dihydroxypropanone-synthesis of (S)-1,2-O-isopropylideneglycerol and (R)-1,2-isopropylideneglycerol. Synthesis 1989, 225-227.
    • (1989) Synthesis , pp. 225-227
    • Aragozzini, F.1    Maconi, E.2    Potenza, D.3    Scolastico, C.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.