Part F | 32
784 Part F Marine Derived Metabolites
32.40
Y. Yamazaki, K. Kohno, H. Yasui, Y. Kiso,
M. Akamatsu, B. Nicholson, G. Deyanat-Yazdi,
S. Neuteboom, B. Potts, G.K. Lloyd, Y. Hayashi:
Tubulin photoaffinity labeling with biotin-tagged
derivatives of potent diketopiperazine antimicrotubule agents, ChemBioChem 9, 3074–3081
(2008)
32.41
P.J. Scheuer, M.T. Hamann: Kahalalide F: A bioactive depsipeptide from the sacoglossan mollusk
Elysia rufescens and the green alga Bryopsis sp.,
J. Am. Chem. Soc. 115, 5825–5826 (1993)
32.42
Y.H. Ling, M. Aracil, J. Jimeno, R. Perez-Soler,
Y. Zou: Molecular pharmacodynamics of PM02734
(elisidepsin) as single agent and in combination with erlotinib; synergisitic activity in human non-small cell lung cancer cell lines and
xenograft models, Eur. J. Cancer 45, 1855–1864
(2009)
32.43
J.M. Frincke, D.J. Faulkner: Antimicrobial
metabolites of the sponge Reniera sp., J. Am.
Chem. Soc. 104, 265–269 (1982)
32.44
H.Y. He, D.J. Faulkner: Renieramycins E and F from
the sponge Reniera sp.: Reassignment of stereochemistry of the renieramycins, J. Org. Chem. 54,
5822–5824 (1989)
32.45
A. Fontana, P. Cavaliere, S. Wahidulla, C.G. Naik,
G. Cimino: A new antitumor isoquinoline alkaloid
from the marine nudibranch Jorunna funebris,
Tetrahedron 56, 7305–7308 (2000)
32.46
J.F.M. Leal, V. García-Hernández, V. Moneo,
A. Domingo, J.A. Bueren-Calabuig, A. Negri,
F. Gago, M.J. Guillén-Navarro, P. Avilés, C. Cuevas,
L.F. García-Fernández, C.M. Galmarini: Molecular
pharmacology and antitumor activity of Zalypsis in several human cancer cell lines, Biochem.
Pharmacol. 78, 162–170 (2009)
32.47
R. Bai, S.J. Friedman, G.R. Pettit, E. Hamel: Dolastatin 15, a potent antimitotic depsipeptide derived from Dolabella auricularia – Interaction
with tubulin and effects on cellular microtubules,
Biochem. Pharmacol. 43, 2637–2645 (1992)
32.48
A. Ray, T. Okouneva, T. Manna, H.P. Miller,
S. Schmid, L. Arthaud, R. Luduena, M.A. Jordan, L. Wilson: Mechanism of action of the
microtubule-targeted antimitotic depsipeptide
tasidotin (formerly ILX651) and its major metabolite tasidotin C-carboxylate, Cancer Res. 67, 3767–
3776 (2007)
32.49
R. Bai, M.C. Edler, P.L. Bonate, T.D. Copeland,
G.R. Pettit, R.F. Luduena, E. Hamel: Intracellular
activation and deactivation of tasidotin, an analog of dolastatin 15: Correlation with cytotoxicity,
Mol. Pharmacol. 75, 218–226 (2009)
32.50
R.H. Feling, G.O. Buchanan, T.J. Mincer,
C.A. Kauffman, P.R. Jensen, W. Fenical: Salinosporamide A: A highly cytotoxic proteasome
inhibitor from a novel microbial source, a marine
bacterium of the new genus Salinospora, Prog.
Chem. Org. Nat. Prod. 42, 355–357 (2003)
32.51
W. Fenical, P.R. Jensen, M.A. Palladino, K.S. Lam,
G.K. Lloyd, B.C. Potts: Discovery and development
of the anticancer agent salinosporamide A (NPI0052), Bioorg. Med. Chem. 17, 2175–2180 (2009)
32.52
M. Groll, R. Huber, B.C.M. Potts: Crystal structures
of salinosporamide A (NPI-0052) and B (NPI-0047)
in complex with the 20S proteasome reveal important consequences of ˇ-lactone ring opening
and a mechanism for irreversible binding, J. Am.
Chem. Soc. 128, 5136–5141 (2006)
32.53
D. Chauhan, L. Catley, G. Li, K. Podar,
T. Hideshima, M. Velankar, C. Mitsiades, N. Mitsiades, H. Yasui, A. Letai, H. Ovaa, C. Berkers,
B. Nicholson, T.H. Chao, S.T. Neuteboom,
P. Richardson, M.A. Palladino, K.C. Anderson:
A novel orally active proteasome inhibitor induces apoptosis in multiple myeloma cells with
mechanisms distinct from bortezomib, Cancer
Cell 8, 407–419 (2005)
32.54
D. Chauhan, A. Singh, M. Brahmandam, K. Podar, T. Hideshima, P. Richardson, N. Munshi,
M.A. Palladino, K.C. Anderson: Combination of
proteasome inhibitors bortezomib and NPI-0052
trigger in vivo synergistic cytotoxicity in multiple
myeloma, Blood 111, 1654–1664 (2008)
32.55
R. Talpir, Y. Benayahu, Y. Kashman, L. Pannell,
M. Schleyer: Hemiasterlin and geodiamolide TA;
two new cytotoxic peptides from the marine
sponge Hemiasterella minor (Kirkpatrick), Tetrahedron Lett. 35, 4453–4456 (1994)
32.56
J.E. Coleman, E.D. de Silva, F. Kong, R.J. Andersen:
Cytotoxic peptides from the marine sponge Cymbastela sp., Tetrahedron 51, 10653–10662 (1995)
32.57
W.R. Gamble, N.A. Durso, R.W. Fuller, C.K. Westergaard, T.R. Johnson, D.L. Sackett, E. Hamel,
J.H. Cardellina, M.R. Boyd: Cytotoxic and tubulininteractive hemiasterlins from Auletta sp. and
Siphonochalina sp. sponges, Bioorg. Med. Chem.
7, 1611–1615 (1999)
32.58
H.J. Anderson, J.E. Coleman, R.J. Andersen,
M. Roberge: Cytotoxic peptides hemiasterlin,
hemiasterlin A and hemiasterlin B induce mitotic
arrest and abnormal spindle formation, Cancer
Chemother. Pharmacol. 39, 223–226 (1997)
32.59
J.E. Coleman, B.O. Patrick, R.J. Andersen, S.J. Rettig: Hemiasterlin methyl ester, Acta Crystallogr.
C52, 1525–1527 (1996)
32.60
F. Loganzo, C.M. Discafani, T. Annable, C. Beyer,
S. Musto, M. Hari, X. Tan, C. Hardy, R. Hernandez, M. Baxter, C. Singanallore, G. Khafizova,
M.S. Poruchynsky, T. Fojo, J.A. Nieman, S. AyralKaloustain, A. Zask, R.J. Andersen, L.M. Greenberger: Antimirotubule agent that circumvents
P-glycoprotein-mediated resistance in vitro and
in vivo, Cancer Res. 63, 1838–1845 (2003)
32.61
M.J. Ratain, S. Undevia, L. Janisch, S. Roman,
P. Mayer, M. Buckwalter, D. Foss, B.L. Hamilton,
J. Fischer, R.M. Bukowski: Phase 1 and pharmacological study of HTI-286, a novel antimicro-
784 Part F Marine Derived Metabolites
32.40
Y. Yamazaki, K. Kohno, H. Yasui, Y. Kiso,
M. Akamatsu, B. Nicholson, G. Deyanat-Yazdi,
S. Neuteboom, B. Potts, G.K. Lloyd, Y. Hayashi:
Tubulin photoaffinity labeling with biotin-tagged
derivatives of potent diketopiperazine antimicrotubule agents, ChemBioChem 9, 3074–3081
(2008)
32.41
P.J. Scheuer, M.T. Hamann: Kahalalide F: A bioactive depsipeptide from the sacoglossan mollusk
Elysia rufescens and the green alga Bryopsis sp.,
J. Am. Chem. Soc. 115, 5825–5826 (1993)
32.42
Y.H. Ling, M. Aracil, J. Jimeno, R. Perez-Soler,
Y. Zou: Molecular pharmacodynamics of PM02734
(elisidepsin) as single agent and in combination with erlotinib; synergisitic activity in human non-small cell lung cancer cell lines and
xenograft models, Eur. J. Cancer 45, 1855–1864
(2009)
32.43
J.M. Frincke, D.J. Faulkner: Antimicrobial
metabolites of the sponge Reniera sp., J. Am.
Chem. Soc. 104, 265–269 (1982)
32.44
H.Y. He, D.J. Faulkner: Renieramycins E and F from
the sponge Reniera sp.: Reassignment of stereochemistry of the renieramycins, J. Org. Chem. 54,
5822–5824 (1989)
32.45
A. Fontana, P. Cavaliere, S. Wahidulla, C.G. Naik,
G. Cimino: A new antitumor isoquinoline alkaloid
from the marine nudibranch Jorunna funebris,
Tetrahedron 56, 7305–7308 (2000)
32.46
J.F.M. Leal, V. García-Hernández, V. Moneo,
A. Domingo, J.A. Bueren-Calabuig, A. Negri,
F. Gago, M.J. Guillén-Navarro, P. Avilés, C. Cuevas,
L.F. García-Fernández, C.M. Galmarini: Molecular
pharmacology and antitumor activity of Zalypsis in several human cancer cell lines, Biochem.
Pharmacol. 78, 162–170 (2009)
32.47
R. Bai, S.J. Friedman, G.R. Pettit, E. Hamel: Dolastatin 15, a potent antimitotic depsipeptide derived from Dolabella auricularia – Interaction
with tubulin and effects on cellular microtubules,
Biochem. Pharmacol. 43, 2637–2645 (1992)
32.48
A. Ray, T. Okouneva, T. Manna, H.P. Miller,
S. Schmid, L. Arthaud, R. Luduena, M.A. Jordan, L. Wilson: Mechanism of action of the
microtubule-targeted antimitotic depsipeptide
tasidotin (formerly ILX651) and its major metabolite tasidotin C-carboxylate, Cancer Res. 67, 3767–
3776 (2007)
32.49
R. Bai, M.C. Edler, P.L. Bonate, T.D. Copeland,
G.R. Pettit, R.F. Luduena, E. Hamel: Intracellular
activation and deactivation of tasidotin, an analog of dolastatin 15: Correlation with cytotoxicity,
Mol. Pharmacol. 75, 218–226 (2009)
32.50
R.H. Feling, G.O. Buchanan, T.J. Mincer,
C.A. Kauffman, P.R. Jensen, W. Fenical: Salinosporamide A: A highly cytotoxic proteasome
inhibitor from a novel microbial source, a marine
bacterium of the new genus Salinospora, Prog.
Chem. Org. Nat. Prod. 42, 355–357 (2003)
32.51
W. Fenical, P.R. Jensen, M.A. Palladino, K.S. Lam,
G.K. Lloyd, B.C. Potts: Discovery and development
of the anticancer agent salinosporamide A (NPI0052), Bioorg. Med. Chem. 17, 2175–2180 (2009)
32.52
M. Groll, R. Huber, B.C.M. Potts: Crystal structures
of salinosporamide A (NPI-0052) and B (NPI-0047)
in complex with the 20S proteasome reveal important consequences of ˇ-lactone ring opening
and a mechanism for irreversible binding, J. Am.
Chem. Soc. 128, 5136–5141 (2006)
32.53
D. Chauhan, L. Catley, G. Li, K. Podar,
T. Hideshima, M. Velankar, C. Mitsiades, N. Mitsiades, H. Yasui, A. Letai, H. Ovaa, C. Berkers,
B. Nicholson, T.H. Chao, S.T. Neuteboom,
P. Richardson, M.A. Palladino, K.C. Anderson:
A novel orally active proteasome inhibitor induces apoptosis in multiple myeloma cells with
mechanisms distinct from bortezomib, Cancer
Cell 8, 407–419 (2005)
32.54
D. Chauhan, A. Singh, M. Brahmandam, K. Podar, T. Hideshima, P. Richardson, N. Munshi,
M.A. Palladino, K.C. Anderson: Combination of
proteasome inhibitors bortezomib and NPI-0052
trigger in vivo synergistic cytotoxicity in multiple
myeloma, Blood 111, 1654–1664 (2008)
32.55
R. Talpir, Y. Benayahu, Y. Kashman, L. Pannell,
M. Schleyer: Hemiasterlin and geodiamolide TA;
two new cytotoxic peptides from the marine
sponge Hemiasterella minor (Kirkpatrick), Tetrahedron Lett. 35, 4453–4456 (1994)
32.56
J.E. Coleman, E.D. de Silva, F. Kong, R.J. Andersen:
Cytotoxic peptides from the marine sponge Cymbastela sp., Tetrahedron 51, 10653–10662 (1995)
32.57
W.R. Gamble, N.A. Durso, R.W. Fuller, C.K. Westergaard, T.R. Johnson, D.L. Sackett, E. Hamel,
J.H. Cardellina, M.R. Boyd: Cytotoxic and tubulininteractive hemiasterlins from Auletta sp. and
Siphonochalina sp. sponges, Bioorg. Med. Chem.
7, 1611–1615 (1999)
32.58
H.J. Anderson, J.E. Coleman, R.J. Andersen,
M. Roberge: Cytotoxic peptides hemiasterlin,
hemiasterlin A and hemiasterlin B induce mitotic
arrest and abnormal spindle formation, Cancer
Chemother. Pharmacol. 39, 223–226 (1997)
32.59
J.E. Coleman, B.O. Patrick, R.J. Andersen, S.J. Rettig: Hemiasterlin methyl ester, Acta Crystallogr.
C52, 1525–1527 (1996)
32.60
F. Loganzo, C.M. Discafani, T. Annable, C. Beyer,
S. Musto, M. Hari, X. Tan, C. Hardy, R. Hernandez, M. Baxter, C. Singanallore, G. Khafizova,
M.S. Poruchynsky, T. Fojo, J.A. Nieman, S. AyralKaloustain, A. Zask, R.J. Andersen, L.M. Greenberger: Antimirotubule agent that circumvents
P-glycoprotein-mediated resistance in vitro and
in vivo, Cancer Res. 63, 1838–1845 (2003)
32.61
M.J. Ratain, S. Undevia, L. Janisch, S. Roman,
P. Mayer, M. Buckwalter, D. Foss, B.L. Hamilton,
J. Fischer, R.M. Bukowski: Phase 1 and pharmacological study of HTI-286, a novel antimicro-