메뉴 건너뛰기




Volumn 46, Issue 9, 2003, Pages 1571-1579

Differential binding modes of diacylglycerol (DAG) and DAG lactones to protein kinase C (PK-C)

Author keywords

[No Author keywords available]

Indexed keywords

DIACYLGLYCEROL; DIACYLGLYCEROL LACTONE DERIVATIVE; GLYCEROL; ISOENZYME; LACTONE DERIVATIVE; PROTEIN KINASE C; UNCLASSIFIED DRUG;

EID: 0037464480     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020476o     Document Type: Article
Times cited : (30)

References (31)
  • 1
    • 0028811653 scopus 로고
    • Protein kinase C structure, function and regulation
    • Newton, A. C. Protein Kinase C: Structure, Function and Regulation. J. Biol. Chem. 1995, 270, 28495-28498.
    • (1995) J. Biol. Chem. , vol.270 , pp. 28495-28498
    • Newton, A.C.1
  • 2
    • 0030389652 scopus 로고    scopus 로고
    • Regulation of protein kinase C: A tale of lipids and proteins
    • Quest, A. F. G. Regulation of protein kinase C: A tale of lipids and proteins. Enzyme Protein 1996, 49, 231-261.
    • (1996) Enzyme Protein , vol.49 , pp. 231-261
    • Quest, A.F.G.1
  • 3
    • 0032104245 scopus 로고    scopus 로고
    • The extended protein kinase C super-family
    • Mellor, H.; Parker, P. J. The extended protein kinase C super-family. Biochem. J. 1998, 332, 281-292.
    • (1998) Biochem. J. , vol.332 , pp. 281-292
    • Mellor, H.1    Parker, P.J.2
  • 4
    • 0032849088 scopus 로고    scopus 로고
    • New insights into the regulation of protein kinase C. and novel phorbol ester receptors
    • Ron, D.; Kazanietz, M. G. New insights into the regulation of protein kinase C. and novel phorbol ester receptors. FASEB J. 2000, 13, 1658-1676.
    • (2000) FASEB J. , vol.13 , pp. 1658-1676
    • Ron, D.1    Kazanietz, M.G.2
  • 5
    • 0020326790 scopus 로고
    • Direct activation of calcium-activated, phospholipid-dependent protein kinase by tumor-promoting phorbol esters
    • Castagna, M.; Takai, Y.; Kaibuchi, K.; Sano, K.; Kikkawa, U.; Nishizuka, Y. Direct activation of calcium-activated, phospholipid-dependent protein kinase by tumor-promoting phorbol esters. J. Biol. Chem., 1982, 257, 7847-7851.
    • (1982) J. Biol. Chem. , vol.257 , pp. 7847-7851
    • Castagna, M.1    Takai, Y.2    Kaibuchi, K.3    Sano, K.4    Kikkawa, U.5    Nishizuka, Y.6
  • 6
    • 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
  • 7
    • 0031466995 scopus 로고    scopus 로고
    • Direct visualization of the translocation of the γ-subspecies of protein kinase C in living cells using fusion proteins with green fluorescent protein
    • Sakai, N.; Sadaki, K.; Ikegaki, N.; Shirai, Y.; Ono, Y.; Saito, N. Direct visualization of the translocation of the γ-subspecies of protein kinase C in living cells using fusion proteins with green fluorescent protein. J. Cell Biol. 1997, 139, 1465-1476.
    • (1997) J. Cell Biol. , vol.139 , pp. 1465-1476
    • Sakai, N.1    Sadaki, K.2    Ikegaki, N.3    Shirai, Y.4    Ono, Y.5    Saito, N.6
  • 8
    • 0032498538 scopus 로고    scopus 로고
    • Green fluorescent protein (GFP)-tagged cysteine-rich domains from protein kinase C as fluorescent indicators for diacylgylcerol signaling in living cells
    • Oancea, E.; Teruel, M. N.; Quest, A. F. G.; Meyer, T. Green fluorescent protein (GFP)-tagged cysteine-rich domains from protein kinase C as fluorescent indicators for diacylgylcerol signaling in living cells. J. Cell Biol. 1998, 140, 485-498.
    • (1998) J. Cell Biol. , vol.140 , pp. 485-498
    • Oancea, E.1    Teruel, M.N.2    Quest, A.F.G.3    Meyer, T.4
  • 9
    • 0028341564 scopus 로고
    • Phosphatidyl-L-serine is necessary for protein kinase C's high affinity interaction with diacylglycerol-containing membranes
    • Newton, A. C.; Keranen, L. M. Phosphatidyl-L-serine is necessary for protein kinase C's high affinity interaction with diacylglycerol-containing membranes. Biochemistry 1994, 33, 661-6658.
    • (1994) Biochemistry , vol.33 , pp. 661-6658
    • Newton, A.C.1    Keranen, L.M.2
  • 10
    • 0030987070 scopus 로고    scopus 로고
    • Regulation of protein kinase C
    • Newton, A. C. Regulation of protein kinase C. Curr. Opin. Cell. Biol. 1997, 9, 161-167.
    • (1997) Curr. Opin. Cell Biol. , vol.9 , pp. 161-167
    • Newton, A.C.1
  • 11
    • 0026451081 scopus 로고
    • Intracelluar signaling by hydrolysis of phospholipids and activation of protein-kinase-C
    • Nishizuka, Y. Intracelluar signaling by hydrolysis of phospholipids and activation of protein-kinase-C. Science 1992, 258, 607-614.
    • (1992) Science , vol.258 , pp. 607-614
    • Nishizuka, Y.1
  • 12
    • 0032582525 scopus 로고    scopus 로고
    • Protein kinase C as a molecular machine for decoding calcium and diacylglycerol signals
    • Oancea, E.; Meyer, T. Protein kinase C as a molecular machine for decoding calcium and diacylglycerol signals. Cell 1998, 95, 307-318.
    • (1998) Cell , vol.95 , pp. 307-318
    • Oancea, E.1    Meyer, T.2
  • 13
    • 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
  • 14
    • 0034599717 scopus 로고    scopus 로고
    • Diacylglycerols with lipophilically equivalent branched acyl chains display high affinity for protein kinase C (PK-C). A direct measure of the effect of constraining the glycerol backbone in DAG lactones
    • Nacro, K.; Bienfait, B.; Lewin, N. E.; Blumberg, P. M.; Marquez, V. E. Diacylglycerols with lipophilically equivalent branched acyl chains display high affinity for protein kinase C (PK-C). A direct measure of the effect of constraining the glycerol backbone in DAG lactones. Bioorg. Med. Chem. Lett. 2000, 10, 653-655.
    • (2000) Bioorg. Med. Chem. Lett. , vol.10 , pp. 653-655
    • Nacro, K.1    Bienfait, B.2    Lewin, N.E.3    Blumberg, P.M.4    Marquez, V.E.5
  • 15
    • 0034624775 scopus 로고    scopus 로고
    • Confromationally 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. Confromationally 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
  • 16
    • 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.; 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.4    Pearce, L.L.5    Lewin, N.E.6    Garfield, S.H.7    Blumberg, P.M.8    Marquez, V.E.9
  • 17
    • 0030901239 scopus 로고    scopus 로고
    • Synthesis of (4S)-hydroxymethyl-(2R)-(2-propyl)butyrolactone: A quest for a practical route to an important hydroxyethylene isostere chiron
    • For compound 6: Hanessian, S.; Abad-Grillo, T.; McNaughton-Smith, G. Synthesis of (4S)-hydroxymethyl-(2R)-(2-propyl)butyrolactone: a quest for a practical route to an important hydroxyethylene isostere chiron. Tetrahedron 1997, 53, 6281-6294.
    • (1997) Tetrahedron , vol.53 , pp. 6281-6294
    • Hanessian, S.1    Abad-Grillo, T.2    McNaughton-Smith, G.3
  • 18
    • 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. A.; 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.A.4    Lewin, N.E.5    Blumberg, P.M.6    Marquez, V.E.7
  • 19
    • 0041411152 scopus 로고    scopus 로고
    • Comparison of the roles of the C1a and C1b domains of protein kinase C alpha in ligand induced translocation in NIH 3T3 cells
    • Bögi, K.; Lorenzo, P. S.; Acs, P.; Szállási, Z.; Wagner, G. S.; Blumberg, P. M. Comparison of the roles of the C1a and C1b domains of protein kinase C alpha in ligand induced translocation in NIH 3T3 cells. FEBS Lett. 1999, 456, 27-30.
    • (1999) FEBS Lett. , vol.456 , pp. 27-30
    • Bögi, K.1    Lorenzo, P.S.2    Acs, P.3    Szállási, Z.4    Wagner, G.S.5    Blumberg, P.M.6
  • 20
    • 0029585123 scopus 로고
    • Atom fragment contribution method for estimating octanol-water partition coefficients
    • KOWWIN 1.63
    • Meylan, W. M.; Howard, Ph. H. Atom Fragment Contribution Method for Estimating Octanol-Water Partition Coefficients. KOWWIN 1.63, Syracuse Research Corp.; http:// esc.syrres.com.20. J. Pharm. Sci. 1995, 84, 83-92.
    • (1995) J. Pharm. Sci. , vol.84 , pp. 83-92
    • Meylan, W.M.1    Howard, Ph.H.2
  • 21
    • 0030032407 scopus 로고    scopus 로고
    • Conformationally constrained analogues of diacylglycerol. 11.1 Ultrapotent protein kinase C ligands based on a chiral 5-disubstituted tetrahydro-2-furanone template
    • Lee, J.; Shaomeng Wang, S.; Milne, G. W. A.; Sharma, R.; Lewin, N. E.; Blumberg, P. M.; Marquez, V. E. Conformationally Constrained Analogues of Diacylglycerol. 11.1 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    Shaomeng Wang, S.2    Milne, G.W.A.3    Sharma, R.4    Lewin, N.E.5    Blumberg, P.M.6    Marquez, V.E.7
  • 22
    • 0030599010 scopus 로고    scopus 로고
    • A fast flexible docking method using an incremental construction algorithm
    • Rarey, M.; Kramer, B.; Lengauer, T.; Klebe, G. A fast flexible docking method using an incremental construction algorithm. J. Mol. Biol. 1996, 261, 470-489.
    • (1996) J. Mol. Biol. , vol.261 , pp. 470-489
    • Rarey, M.1    Kramer, B.2    Lengauer, T.3    Klebe, G.4
  • 23
    • 0028854034 scopus 로고
    • Molecular recognition of receptor sites using a genetic algorithm with a description of desolvation
    • Jones, G.; Willett, P.; Glen, R. C. Molecular recognition of receptor sites using a genetic algorithm with a description of desolvation. J. Mol. Biol. 1995, 245, 43-53.
    • (1995) J. Mol. Biol. , vol.245 , pp. 43-53
    • Jones, G.1    Willett, P.2    Glen, R.C.3
  • 24
    • 0032402377 scopus 로고    scopus 로고
    • Conformationally constrained analogues of diacylglycerol (DAG). 15. The indispensable role of the sn-1 and sn-2 carbonyls in the binding of DAG-lactones to protein kinase C (PK-C)
    • Benzaria, S.; Bienfait, B.; Nacro, K.; Wang, S.; Lewin, N. E.; Beheshti, M.; Blumberg, P. M.; Marquez, V. E. Conformationally constrained analogues of diacylglycerol (DAG). 15. The indispensable role of the sn-1 and sn-2 carbonyls in the binding of DAG-lactones to protein kinase C (PK-C). Bioorg. Med. Chem. Lett. 1998, 8, 3403-3408.
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 3403-3408
    • Benzaria, S.1    Bienfait, B.2    Nacro, K.3    Wang, S.4    Lewin, N.E.5    Beheshti, M.6    Blumberg, P.M.7    Marquez, V.E.8
  • 25
    • 0344340981 scopus 로고    scopus 로고
    • Numbering of the PK-C residues is internal to the C1 domain (e.g., Gly 23 corresponds to Gly 253 in PK-Cδ C1b, Gly 59 in PK-Cα C1a, and Gly 124 in PK-Cα C1b)
    • Numbering of the PK-C residues is internal to the C1 domain (e.g., Gly 23 corresponds to Gly 253 in PK-Cδ C1b, Gly 59 in PK-Cα C1a, and Gly 124 in PK-Cα C1b).
  • 26
    • 0345203471 scopus 로고    scopus 로고
    • Insight II and QUANTA 97 are products of Accelrys Inc., 9685 Scranton Road, San Diego, CA 92121-3752
    • Insight II and QUANTA 97 are products of Accelrys Inc., 9685 Scranton Road, San Diego, CA 92121-3752 (www.accelrys.com).
  • 27
    • 0031576989 scopus 로고    scopus 로고
    • Side chain placement from a backbone-dependent rotamer library: A new tool for homology modeling
    • Bower, M.; Cohen, F. E.; Dunbrack, R. L., Jr. Side chain placement from a backbone-dependent rotamer library: A new tool for homology modeling. J. Mol. Biol. 1997, 267, 1268-1282.
    • (1997) J. Mol. Biol. , vol.267 , pp. 1268-1282
    • Bower, M.1    Cohen, F.E.2    Dunbrack R.L., Jr.3
  • 28
    • 0345635422 scopus 로고    scopus 로고
    • FlexX and SYBYL are products of Tripos Inc., 1699 South Hanley Road, St. Louis, MO 63144-2913
    • FlexX and SYBYL are products of Tripos Inc., 1699 South Hanley Road, St. Louis, MO 63144-2913 (www.tripos.com).
  • 30
    • 84986505827 scopus 로고
    • Validation of the general purpose QUANTA 3.2/CHARMm force field
    • Momany, F. A.; Rone, R. Validation of the general purpose QUANTA 3.2/CHARMm force field. J. Comput. Chem. 1992, 13, 888-900.
    • (1992) J. Comput. Chem. , vol.13 , pp. 888-900
    • Momany, F.A.1    Rone, R.2
  • 31
    • 0015222647 scopus 로고
    • The interpretation of protein structures: Estimation of static accessibility
    • Lee, B.; Richards, F. M. The interpretation of protein structures: Estimation of static accessibility. J. Mol. Biol. 1971, 55, 379-400.
    • (1971) J. Mol. Biol. , vol.55 , pp. 379-400
    • Lee, B.1    Richards, F.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.