-
1
-
-
0034739423
-
-
Cueto, M.; Jensen, P. R.; Fenical, W. N-Methylsansalvamide, a cytotoxic cyclic depsipeptide from a marine fungus of the genus Fusarium. Photochemistry 2000, 55, 223-226.
-
Cueto, M.; Jensen, P. R.; Fenical, W. N-Methylsansalvamide, a cytotoxic cyclic depsipeptide from a marine fungus of the genus Fusarium. Photochemistry 2000, 55, 223-226.
-
-
-
-
2
-
-
0032977819
-
Mechanism of inhibition of a poxvirus topoisomerase by the marine natural product Sansalvamide A
-
Hwang, Y.; Rowley, D.; Rhodes, D.; Gertsch, J.; Fenical, W.; Bushman, F. Mechanism of inhibition of a poxvirus topoisomerase by the marine natural product Sansalvamide A. Mol. Pharmacol. 1999, 55, 1049-1053.
-
(1999)
Mol. Pharmacol
, vol.55
, pp. 1049-1053
-
-
Hwang, Y.1
Rowley, D.2
Rhodes, D.3
Gertsch, J.4
Fenical, W.5
Bushman, F.6
-
3
-
-
0033538036
-
-
Belofsky, G. N.; Jensen, P. R.; Fenical, W. Sansalvamide: A new cytotoxic cyclic depsipeptide produced by a marine fungus of the genus Fusarium. Tetrahedron Lett. 1999, 40, 2913-2916.
-
Belofsky, G. N.; Jensen, P. R.; Fenical, W. Sansalvamide: A new cytotoxic cyclic depsipeptide produced by a marine fungus of the genus Fusarium. Tetrahedron Lett. 1999, 40, 2913-2916.
-
-
-
-
4
-
-
33745592766
-
Synthesis of Sansalvamide A derivatives and their cytotoxicity in the colon cancer cell line HT-29
-
Styers, T. J.; Kekec, A.; Rodriguez, R.; Brown, J. D.; Cajica, J.; Pan, P.-S.; Parry, E.; Carroll, C. L.; Medina, I.; Corral, R.; Lapera, S.; Otrubova, K.; Pan, C.-M.; McGuire, K. L.; McAlpine, S. R. Synthesis of Sansalvamide A derivatives and their cytotoxicity in the colon cancer cell line HT-29. Bioorg. Med. Chem. 2006, 14, 5625-5631.
-
(2006)
Bioorg. Med. Chem
, vol.14
, pp. 5625-5631
-
-
Styers, T.J.1
Kekec, A.2
Rodriguez, R.3
Brown, J.D.4
Cajica, J.5
Pan, P.-S.6
Parry, E.7
Carroll, C.L.8
Medina, I.9
Corral, R.10
Lapera, S.11
Otrubova, K.12
Pan, C.-M.13
McGuire, K.L.14
McAlpine, S.R.15
-
5
-
-
33947246678
-
Synthesis of second generation Sansalvamide A derivatives: Novel templates as potent antitumor agents
-
Rodriguez, R.; Pan, P.-S.; Pan, C.-M.; Ravula, S.; Lapera, S.; Singh, E.; Styers, T. J.; Brown, J. D.; Cajica, J.; Parry, E.; Otrubova, K.; McAlpine, S. R. Synthesis of second generation Sansalvamide A derivatives: Novel templates as potent antitumor agents. J. Org. Chem. 2007, 72, 1980-2002.
-
(2007)
J. Org. Chem
, vol.72
, pp. 1980-2002
-
-
Rodriguez, R.1
Pan, P.-S.2
Pan, C.-M.3
Ravula, S.4
Lapera, S.5
Singh, E.6
Styers, T.J.7
Brown, J.D.8
Cajica, J.9
Parry, E.10
Otrubova, K.11
McAlpine, S.R.12
-
6
-
-
18644371080
-
-
Liu, S.; Gu, W.; D, L.; Ding, X.-Z.; Ujiki, M.; Adrian, T. E.; Soff, G. A.; Silverman, R. B. N-Methylsansalvamide A peptide analogues. Potent new antitumor agents. J. Med. Chem. 2005, 48, 3630-3638.
-
Liu, S.; Gu, W.; D, L.; Ding, X.-Z.; Ujiki, M.; Adrian, T. E.; Soff, G. A.; Silverman, R. B. N-Methylsansalvamide A peptide analogues. Potent new antitumor agents. J. Med. Chem. 2005, 48, 3630-3638.
-
-
-
-
7
-
-
34547855100
-
Identification of compounds potent against pancreatic cancer cell lines
-
Pan, P.-S.; McGuire, K. L.; McAlpine, S. R. Identification of compounds potent against pancreatic cancer cell lines. Bioorganic and Med. Chem. Lett. 2007, 17, 5072-5077.
-
(2007)
Bioorganic and Med. Chem. Lett
, vol.17
, pp. 5072-5077
-
-
Pan, P.-S.1
McGuire, K.L.2
McAlpine, S.R.3
-
8
-
-
30544431590
-
A novel peptide sansalvamide A analogue inhibits pancreatic cancer cell growth through G0/G1 cell-cycle arrest
-
Ujiki, M.; Milam, B.; Ding, X.-Z.; Roginsky, A. B.; Salabat, M. R.; Talamonti, M. S.; Bell, R. H.; Gu, W.; Silverman, R. B.; Adrian, T. E. A novel peptide sansalvamide A analogue inhibits pancreatic cancer cell growth through G0/G1 cell-cycle arrest. Biochem. Biophys. Res. Commun. 2006, 340, 1224-1228.
-
(2006)
Biochem. Biophys. Res. Commun
, vol.340
, pp. 1224-1228
-
-
Ujiki, M.1
Milam, B.2
Ding, X.-Z.3
Roginsky, A.B.4
Salabat, M.R.5
Talamonti, M.S.6
Bell, R.H.7
Gu, W.8
Silverman, R.B.9
Adrian, T.E.10
-
9
-
-
33244483270
-
Synthesis and novel structure-activity relationships of potent Sansalvamide A derivatives
-
Otrubova, K.; Styers, T. J.; Pan, P.-S.; Rodriguez, R.; McGuire, K. L.; McAlpine, S. R. Synthesis and novel structure-activity relationships of potent Sansalvamide A derivatives Chem. Commun. 2006, 1033-1034.
-
(2006)
Chem. Commun
, pp. 1033-1034
-
-
Otrubova, K.1
Styers, T.J.2
Pan, P.-S.3
Rodriguez, R.4
McGuire, K.L.5
McAlpine, S.R.6
-
10
-
-
23944442706
-
Synthesis and cytotoxicity of novel Sansalvamide A derivatives
-
Carroll, C. L.; Johnston, J. V. C.; Kekec, A.; Brown, J. D.; Parry, E.; Cajica, J.; Medina, I.; Cook, K. M.; Corral, R.; Pan, P.-S.; McAlpine, S. R. Synthesis and cytotoxicity of novel Sansalvamide A derivatives. Org. Lett. 2005, 7, 3481-3484.
-
(2005)
Org. Lett
, vol.7
, pp. 3481-3484
-
-
Carroll, C.L.1
Johnston, J.V.C.2
Kekec, A.3
Brown, J.D.4
Parry, E.5
Cajica, J.6
Medina, I.7
Cook, K.M.8
Corral, R.9
Pan, P.-S.10
McAlpine, S.R.11
-
11
-
-
0034676534
-
Rapid, high-yield, solid-phase synthesis of the antitumor antibiotic Sansalvamide A using a side-chain-tethered phenylalanine building block
-
Lee, Y.; Silverman, R. B. Rapid, high-yield, solid-phase synthesis of the antitumor antibiotic Sansalvamide A using a side-chain-tethered phenylalanine building block. Org. Lett. 2000, 2, 3743-3746.
-
(2000)
Org. Lett
, vol.2
, pp. 3743-3746
-
-
Lee, Y.1
Silverman, R.B.2
-
12
-
-
0037078829
-
Solid-phase, Pd-catalyzed silicon-aryl carbon bond formation. Synthesis of Sansalvamide A peptide
-
Gu, W.; Liu, S.; Silverman, R. B. Solid-phase, Pd-catalyzed silicon-aryl carbon bond formation. Synthesis of Sansalvamide A peptide. Org. Lett. 2002, 4, 4171-4174.
-
(2002)
Org. Lett
, vol.4
, pp. 4171-4174
-
-
Gu, W.1
Liu, S.2
Silverman, R.B.3
-
13
-
-
39149128655
-
-
50 ∼ 5 μM.
-
50 ∼ 5 μM.
-
-
-
-
14
-
-
33845309676
-
N-methylated cyclic pentaalanine peptides as template structures
-
Chatterjee, J.; Mierke, D. F.; Kessler, H. N-methylated cyclic pentaalanine peptides as template structures. J. Am. Chem. Soc. 2006, 128, 15164-15172.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 15164-15172
-
-
Chatterjee, J.1
Mierke, D.F.2
Kessler, H.3
-
15
-
-
33750309548
-
The conformation of cyclo(-D-pro-ala-) as a model for cyclic pentapeptides of the DL type
-
Heller, M.; Sukopp, M.; Tsomaia, N.; John, M.; Mierke, D. F.; Reif, B.; Kessler, H. The conformation of cyclo(-D-pro-ala-) as a model for cyclic pentapeptides of the DL type. J. Am. Chem. Soc. 2006, 128, 13806-13814.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 13806-13814
-
-
Heller, M.1
Sukopp, M.2
Tsomaia, N.3
John, M.4
Mierke, D.F.5
Reif, B.6
Kessler, H.7
-
16
-
-
17244370796
-
Over one hundred peptide-activated G protein-coupled receptros recognized ligands with turn structure
-
Tyndall, J. D.; Pfieiffer, B.; Abbenante, G.; Fairlie, D. P. Over one hundred peptide-activated G protein-coupled receptros recognized ligands with turn structure. Chem. Rev. 2005, 105, 793-826.
-
(2005)
Chem. Rev
, vol.105
, pp. 793-826
-
-
Tyndall, J.D.1
Pfieiffer, B.2
Abbenante, G.3
Fairlie, D.P.4
-
17
-
-
0029805817
-
-
Viles, J. H.; Mitchell, J. B.; L., G. S.; Doyle, P. M.; harris, C. J.; Sadler, P. J.; Thornton, J. M. Multiple solution conformations of the integrin-binding cyclic pentapeptide cyclo(Ser-D-Leu-Asp-Val-Pro) analysis of the (phi, psi) space available to the cyclic pentapeptides. Eur. J. Biochem. 1996, 242, 352-362.
-
Viles, J. H.; Mitchell, J. B.; L., G. S.; Doyle, P. M.; harris, C. J.; Sadler, P. J.; Thornton, J. M. Multiple solution conformations of the integrin-binding cyclic pentapeptide cyclo(Ser-D-Leu-Asp-Val-Pro) analysis of the (phi, psi) space available to the cyclic pentapeptides. Eur. J. Biochem. 1996, 242, 352-362.
-
-
-
-
18
-
-
39149084931
-
-
water), is a well established measure of the compound's hydrophilicity. Low hydrophilicities and, therefore, high logP values cause poor absorption or permeation. It has been shown for compounds to have a reasonable probability of being well absorbed, their logP value must not be greater than 5.0. The distribution of calculated logP values of more than 3000 drugs on the market underlines this fact.
-
water), is a well established measure of the compound's hydrophilicity. Low hydrophilicities and, therefore, high logP values cause poor absorption or permeation. It has been shown for compounds to have a reasonable probability of being well absorbed, their logP value must not be greater than 5.0. The distribution of calculated logP values of more than 3000 drugs on the market underlines this fact.
-
-
-
-
19
-
-
0028197288
-
Absorption of peptide and peptidimimetic drugs
-
Amidon, G. L.; Lee, H. J. Absorption of peptide and peptidimimetic drugs. Annu. Rev. Pharmacol. Toxicol. 1994, 34, 321-341.
-
(1994)
Annu. Rev. Pharmacol. Toxicol
, vol.34
, pp. 321-341
-
-
Amidon, G.L.1
Lee, H.J.2
-
20
-
-
0022930160
-
Synthesis of cyclosporin and analogues: Structural and conformational requirements for immunosuppressive activity
-
Wenger, R. M. Synthesis of cyclosporin and analogues: Structural and conformational requirements for immunosuppressive activity. Prog. Allergy 1986, 38, 46-64.
-
(1986)
Prog. Allergy
, vol.38
, pp. 46-64
-
-
Wenger, R.M.1
-
21
-
-
15544379805
-
Watching peptide drugs grow up
-
Marx, V. Watching peptide drugs grow up. Chem. Eng. News 2005, 83, 17-24.
-
(2005)
Chem. Eng. News
, vol.83
, pp. 17-24
-
-
Marx, V.1
-
22
-
-
15544379805
-
Giving biotechnology a chemical push
-
Marx, V. Giving biotechnology a chemical push. Chem. Eng. News 2005, 83, 17-24.
-
(2005)
Chem. Eng. News
, vol.83
, pp. 17-24
-
-
Marx, V.1
-
23
-
-
0036158878
-
Peptides as drugs: Is there a market
-
Loffet, A. Peptides as drugs: Is there a market. Eur. Pept. Soc. 2002, 8, 1-7.
-
(2002)
Eur. Pept. Soc
, vol.8
, pp. 1-7
-
-
Loffet, A.1
-
24
-
-
29144464196
-
High-yielding macrocyclization conditions used in the synthesis of novel Sansalvamide A derivatives
-
Styers, T. J.; Rodriguez, R.; Pan, P.-S.; McAlpine, S. R. High-yielding macrocyclization conditions used in the synthesis of novel Sansalvamide A derivatives. Tetrahedron Lett. 2006, 47, 515-517.
-
(2006)
Tetrahedron Lett
, vol.47
, pp. 515-517
-
-
Styers, T.J.1
Rodriguez, R.2
Pan, P.-S.3
McAlpine, S.R.4
-
25
-
-
39149135140
-
-
1H NMR.
-
1H NMR.
-
-
-
-
26
-
-
33947240524
-
-
Unpublished results from the Guy lab at the Department of Chemical Biology and Therapeutics, Memphis, TN 38103, and published results from our lab show that the use of several coupling reagents facilitates formation of the peptide bond in high yields
-
Unpublished results from the Guy lab at the Department of Chemical Biology and Therapeutics, St Jude Children's Research Hospital, Memphis, TN 38103, and published results from our lab show that the use of several coupling reagents facilitates formation of the peptide bond in high yields.
-
Children's Research Hospital
-
-
Jude, S.1
-
27
-
-
0037666109
-
Novel antibiotics: Macrocyclic peptides designed to trap Holliday junctions
-
Bolla, M. L.; Azevedo, E. V.; Smith, J. M.; Taylor, R. E.; Ranjit, D. K.; Segall, A. M.; McAlpine, S. R. Novel antibiotics: Macrocyclic peptides designed to trap Holliday junctions. Org. Lett. 2003, 5, 109-112.
-
(2003)
Org. Lett
, vol.5
, pp. 109-112
-
-
Bolla, M.L.1
Azevedo, E.V.2
Smith, J.M.3
Taylor, R.E.4
Ranjit, D.K.5
Segall, A.M.6
McAlpine, S.R.7
-
28
-
-
5644288611
-
Novel antibiotics: Second generation macrocyclic peptides designed to trap Holliday junctions
-
Liotta, L. A.; Medina, I.; Robinson, J. L.; Carroll, C. L.; Pan, P.-S.; Corral, R.; Johnston, J. V. C.; Cook, K. M.; Curtis, F. A.; Sharpies, G. J.; McAlpine, S. R. Novel antibiotics: Second generation macrocyclic peptides designed to trap Holliday junctions. Tetrahedron Lett. 2004, 45, 8447-8450.
-
(2004)
Tetrahedron Lett
, vol.45
, pp. 8447-8450
-
-
Liotta, L.A.1
Medina, I.2
Robinson, J.L.3
Carroll, C.L.4
Pan, P.-S.5
Corral, R.6
Johnston, J.V.C.7
Cook, K.M.8
Curtis, F.A.9
Sharpies, G.J.10
McAlpine, S.R.11
-
29
-
-
39149099708
-
-
50 data are shown in the Supporting Information.
-
50 data are shown in the Supporting Information.
-
-
-
-
31
-
-
39149091964
-
-
NOESY data showed stronger cross peaks than ROESY data
-
NOESY data showed stronger cross peaks than ROESY data.
-
-
-
-
32
-
-
33144469997
-
Effects of amino acid chirality and the chemical linker on the cell permeation characteristics of cyclic prodrugs of opioid peptides
-
Liederer, B. M.; Fuchs, T.; Vander Velde, D.; Siahaan, T. J.; Borchardt, R. T. Effects of amino acid chirality and the chemical linker on the cell permeation characteristics of cyclic prodrugs of opioid peptides. J. Med. Chem. 2006, 49, 1261-1270.
-
(2006)
J. Med. Chem
, vol.49
, pp. 1261-1270
-
-
Liederer, B.M.1
Fuchs, T.2
Vander Velde, D.3
Siahaan, T.J.4
Borchardt, R.T.5
-
33
-
-
39149125039
-
-
CoMFA determines the most likely conformation of the active compounds and establishes specific interactions that appear important for cytotoxicity. CoMFA is a modeling projection of a pharmacophore map, as derived by partial least squares, which are fit to experimental inhibition data by a weighted sum of spatial interaction terms between a probe atom and a manifold of related ligand structures. These interaction terms are carefully aligned according to conserved structural features
-
CoMFA determines the most likely conformation of the active compounds and establishes specific interactions that appear important for cytotoxicity. CoMFA is a modeling projection of a pharmacophore map, as derived by partial least squares, which are fit to experimental inhibition data by a weighted sum of spatial interaction terms between a probe atom and a manifold of related ligand structures. These interaction terms are carefully aligned according to conserved structural features.
-
-
-
-
34
-
-
39149092295
-
-
The Tripos Associates, St. Louis, MO 20006
-
SYBYL 7.2, The Tripos Associates, St. Louis, MO 20006.
-
SYBYL 7.2
-
-
-
35
-
-
84988115618
-
Validation of the general purpose Tripos 5.2 force field
-
Clark, M.; Cramer, R. D. I.; Van Opdenbosch, N. Validation of the general purpose Tripos 5.2 force field. J. Comput. Chem. 1989, 10, 982-1012.
-
(1989)
J. Comput. Chem
, vol.10
, pp. 982-1012
-
-
Clark, M.1
Cramer, R.D.I.2
Van Opdenbosch, N.3
-
36
-
-
0027672324
-
Sample-distance partial least squares: PLS optimized for many variables, with application to CoMFA
-
Bush, B. L.; Nachbar, R. B. Sample-distance partial least squares: PLS optimized for many variables, with application to CoMFA. J. Comput.-Aided Mol. Des. 1993, 7, 587-619.
-
(1993)
J. Comput.-Aided Mol. Des
, vol.7
, pp. 587-619
-
-
Bush, B.L.1
Nachbar, R.B.2
|