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PDBsum entry 1tft
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Contents |
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* Residue conservation analysis
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PDB id:
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Apoptosis
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Title:
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Nmr structure of an antagonists of the xiap-caspase-9 interaction complexed to the bir3 domain of xiap
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Structure:
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Baculoviral iap repeat-containing protein 4. Chain: a. Fragment: bir3 of xiap: residues 241-356. Synonym: inhibitor of apoptosis protein 3, x-linked inhibitor of apoptosis protein, x-linked iap, iap-like protein, hilp. Engineered: yes
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Source:
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Homo sapiens. Human. Organism_taxid: 9606. Gene: birc4, api3, iap3, xiap. Expressed in: escherichia coli. Expression_system_taxid: 562.
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NMR struc:
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1 models
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Authors:
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T.K.Oost,C.Sun,R.C.Armstrong,A.S.Al-Assaad,S.F.Betz,T.L.Deckwerth, S.W.Elmore,R.P.Meadows,E.T.Olejniczak,A.K.Oleksijew,T.Oltersdorf, S.H.Rosenberg,A.R.Shoemaker,H.Zou,S.W.Fesik
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Key ref:
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T.K.Oost
et al.
(2004).
Discovery of potent antagonists of the antiapoptotic protein XIAP for the treatment of cancer.
J Med Chem,
47,
4417-4426.
PubMed id:
DOI:
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Date:
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27-May-04
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Release date:
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03-May-05
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PROCHECK
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Headers
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References
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P98170
(XIAP_HUMAN) -
E3 ubiquitin-protein ligase XIAP from Homo sapiens
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Seq:
Struc:
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497 a.a.
117 a.a.*
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Key: |
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PfamA domain |
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Secondary structure |
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CATH domain |
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*
PDB and UniProt seqs differ
at 1 residue position (black
cross)
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Enzyme class:
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E.C.2.3.2.27
- RING-type E3 ubiquitin transferase.
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Reaction:
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S-ubiquitinyl-[E2 ubiquitin-conjugating enzyme]-L-cysteine + [acceptor protein]-L-lysine = [E2 ubiquitin-conjugating enzyme]-L-cysteine + N6- ubiquitinyl-[acceptor protein]-L-lysine
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DOI no:
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J Med Chem
47:4417-4426
(2004)
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PubMed id:
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Discovery of potent antagonists of the antiapoptotic protein XIAP for the treatment of cancer.
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T.K.Oost,
C.Sun,
R.C.Armstrong,
A.S.Al-Assaad,
S.F.Betz,
T.L.Deckwerth,
H.Ding,
S.W.Elmore,
R.P.Meadows,
E.T.Olejniczak,
A.Oleksijew,
T.Oltersdorf,
S.H.Rosenberg,
A.R.Shoemaker,
K.J.Tomaselli,
H.Zou,
S.W.Fesik.
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ABSTRACT
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Inhibitor of apoptosis (IAP) proteins are overexpressed in many cancers and have
been implicated in tumor growth, pathogenesis, and resistance to chemo- or
radiotherapy. On the basis of the NMR structure of a SMAC peptide complexed with
the BIR3 domain of X-linked IAP (XIAP), a novel series of XIAP antagonists was
discovered. The most potent compounds in this series bind to the baculovirus IAP
repeat 3 (BIR3) domain of XIAP with single-digit nanomolar affinity and promote
cell death in several human cancer cell lines. In a MDA-MB-231 breast cancer
mouse xenograft model, these XIAP antagonists inhibited the growth of tumors.
Close structural analogues that showed only weak binding to the XIAP-BIR3 domain
were inactive in the cellular assays and showed only marginal in vivo activity.
Our results are consistent with a mechanism in which ligands for the BIR3 domain
of XIAP induce apoptosis by freeing up caspases. The present study validates the
BIR3 domain of XIAP as a target and supports the use of small molecule XIAP
antagonists as a potential therapy for cancers that overexpress XIAP.
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Literature references that cite this PDB file's key reference
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PubMed id
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Reference
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S.Fulda,
and
D.Vucic
(2012).
Targeting IAP proteins for therapeutic intervention in cancer.
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Nat Rev Drug Discov,
11,
109-124.
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M.S.Ola,
M.Nawaz,
and
H.Ahsan
(2011).
Role of Bcl-2 family proteins and caspases in the regulation of apoptosis.
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Mol Cell Biochem,
351,
41-58.
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T.S.Griffith,
T.A.Kucaba,
M.A.O'Donnell,
J.Burns,
C.Benetatos,
M.A.McKinlay,
S.Condon,
and
S.Chunduru
(2011).
Sensitization of human bladder tumor cells to TNF-related apoptosis-inducing ligand (TRAIL)-induced apoptosis with a small molecule IAP antagonist.
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Apoptosis,
16,
13-26.
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A.Mohr,
S.M.Albarenque,
L.Deedigan,
R.Yu,
M.Reidy,
S.Fulda,
and
R.M.Zwacka
(2010).
Targeting of XIAP combined with systemic mesenchymal stem cell-mediated delivery of sTRAIL ligand inhibits metastatic growth of pancreatic carcinoma cells.
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Stem Cells,
28,
2109-2120.
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B.Z.Carter,
D.H.Mak,
W.D.Schober,
E.Koller,
C.Pinilla,
L.T.Vassilev,
J.C.Reed,
and
M.Andreeff
(2010).
Simultaneous activation of p53 and inhibition of XIAP enhance the activation of apoptosis signaling pathways in AML.
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Blood,
115,
306-314.
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D.Lecis,
C.Drago,
L.Manzoni,
P.Seneci,
C.Scolastico,
E.Mastrangelo,
M.Bolognesi,
A.Anichini,
H.Kashkar,
H.Walczak,
and
D.Delia
(2010).
Novel SMAC-mimetics synergistically stimulate melanoma cell death in combination with TRAIL and Bortezomib.
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Br J Cancer,
102,
1707-1716.
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E.J.Dean,
T.Ward,
C.Pinilla,
R.Houghten,
K.Welsh,
G.Makin,
M.Ranson,
and
C.Dive
(2010).
A small molecule inhibitor of XIAP induces apoptosis and synergises with vinorelbine and cisplatin in NSCLC.
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Br J Cancer,
102,
97.
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F.Cossu,
F.Malvezzi,
G.Canevari,
E.Mastrangelo,
D.Lecis,
D.Delia,
P.Seneci,
C.Scolastico,
M.Bolognesi,
and
M.Milani
(2010).
Recognition of Smac-mimetic compounds by the BIR domain of cIAP1.
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Protein Sci,
19,
2418-2429.
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PDB codes:
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J.Scheper,
M.Guerra-Rebollo,
G.Sanclimens,
A.Moure,
I.Masip,
D.González-Ruiz,
N.Rubio,
B.Crosas,
O.Meca-Cortés,
N.Loukili,
V.Plans,
A.Morreale,
J.Blanco,
A.R.Ortiz,
A.Messeguer,
and
T.M.Thomson
(2010).
Protein-protein interaction antagonists as novel inhibitors of non-canonical polyubiquitylation.
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PLoS One,
5,
e11403.
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P.D.Mace,
S.Shirley,
and
C.L.Day
(2010).
Assembling the building blocks: structure and function of inhibitor of apoptosis proteins.
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Cell Death Differ,
17,
46-53.
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R.Takamatsu,
E.Takeshima,
C.Ishikawa,
K.Yamamoto,
H.Teruya,
K.Heuner,
F.Higa,
J.Fujita,
and
N.Mori
(2010).
Inhibition of Akt/GSK3beta signalling pathway by Legionella pneumophila is involved in induction of T-cell apoptosis.
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Biochem J,
427,
57-67.
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A.Krieg,
R.G.Correa,
J.B.Garrison,
G.Le Negrate,
K.Welsh,
Z.Huang,
W.T.Knoefel,
and
J.C.Reed
(2009).
XIAP mediates NOD signaling via interaction with RIP2.
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Proc Natl Acad Sci U S A,
106,
14524-14529.
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C.D.Moore,
H.Wu,
B.Bolaños,
S.Bergqvist,
A.Brooun,
T.Pauly,
and
D.Nowlin
(2009).
Structural and biophysical characterization of XIAP BIR3 G306E mutant: insights in protein dynamics and application for fragment-based drug design.
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Chem Biol Drug Des,
74,
212-223.
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L.Kleinberg,
and
B.Davidson
(2009).
Cell survival and apoptosis-related molecules in cancer cells in effusions: a comprehensive review.
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Diagn Cytopathol,
37,
613-624.
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M.E.Shawgo,
S.N.Shelton,
and
J.D.Robertson
(2009).
Caspase-9 activation by the apoptosome is not required for fas-mediated apoptosis in type II Jurkat cells.
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J Biol Chem,
284,
33447-33455.
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M.Fakler,
S.Loeder,
M.Vogler,
K.Schneider,
I.Jeremias,
K.M.Debatin,
and
S.Fulda
(2009).
Small molecule XIAP inhibitors cooperate with TRAIL to induce apoptosis in childhood acute leukemia cells and overcome Bcl-2-mediated resistance.
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Blood,
113,
1710-1722.
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M.Orzáez,
A.Gortat,
L.Mondragón,
and
E.Pérez-Payá
(2009).
Peptides and peptide mimics as modulators of apoptotic pathways.
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ChemMedChem,
4,
146-160.
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S.Fulda
(2009).
Inhibitor of apoptosis proteins in hematological malignancies.
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Leukemia,
23,
467-476.
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S.Fulda
(2009).
Cell death in hematological tumors.
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Apoptosis,
14,
409-423.
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S.Fulda
(2009).
Therapeutic opportunities for counteracting apoptosis resistance in childhood leukaemia.
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Br J Haematol,
145,
441-454.
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S.H.Vellanki,
A.Grabrucker,
S.Liebau,
C.Proepper,
A.Eramo,
V.Braun,
T.Boeckers,
K.M.Debatin,
and
S.Fulda
(2009).
Small-molecule XIAP inhibitors enhance gamma-irradiation-induced apoptosis in glioblastoma.
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Neoplasia,
11,
743-752.
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W.Sun,
Z.Nikolovska-Coleska,
D.Qin,
H.Sun,
C.Y.Yang,
L.Bai,
S.Qiu,
Y.Wang,
D.Ma,
and
S.Wang
(2009).
Design, synthesis, and evaluation of potent, nonpeptidic mimetics of second mitochondria-derived activator of caspases.
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J Med Chem,
52,
593-596.
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B.P.Eckelman,
M.Drag,
S.J.Snipas,
and
G.S.Salvesen
(2008).
The mechanism of peptide-binding specificity of IAP BIR domains.
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Cell Death Differ,
15,
920-928.
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B.Zhang,
Z.Nikolovska-Coleska,
Y.Zhang,
L.Bai,
S.Qiu,
C.Y.Yang,
H.Sun,
S.Wang,
and
Y.Wu
(2008).
Design, synthesis, and evaluation of tricyclic, conformationally constrained small-molecule mimetics of second mitochondria-derived activator of caspases.
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J Med Chem,
51,
7352-7355.
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C.Obiol-Pardo,
J.M.Granadino-Roldán,
and
J.Rubio-Martinez
(2008).
Protein-protein recognition as a first step towards the inhibition of XIAP and Survivin anti-apoptotic proteins.
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J Mol Recognit,
21,
190-204.
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E.C.LaCasse,
D.J.Mahoney,
H.H.Cheung,
S.Plenchette,
S.Baird,
and
R.G.Korneluk
(2008).
IAP-targeted therapies for cancer.
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Oncogene,
27,
6252-6275.
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H.A.Harrington,
K.L.Ho,
S.Ghosh,
and
K.C.Tung
(2008).
Construction and analysis of a modular model of caspase activation in apoptosis.
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Theor Biol Med Model,
5,
26.
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H.Sun,
J.A.Stuckey,
Z.Nikolovska-Coleska,
D.Qin,
J.L.Meagher,
S.Qiu,
J.Lu,
C.Y.Yang,
N.G.Saito,
and
S.Wang
(2008).
Structure-based design, synthesis, evaluation, and crystallographic studies of conformationally constrained Smac mimetics as inhibitors of the X-linked inhibitor of apoptosis protein (XIAP).
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J Med Chem,
51,
7169-7180.
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PDB code:
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H.Sun,
Z.Nikolovska-Coleska,
C.Y.Yang,
D.Qian,
J.Lu,
S.Qiu,
L.Bai,
Y.Peng,
Q.Cai,
and
S.Wang
(2008).
Design of small-molecule peptidic and nonpeptidic Smac mimetics.
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Acc Chem Res,
41,
1264-1277.
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J.M.Hallett,
A.E.Leitch,
N.A.Riley,
R.Duffin,
C.Haslett,
and
A.G.Rossi
(2008).
Novel pharmacological strategies for driving inflammatory cell apoptosis and enhancing the resolution of inflammation.
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Trends Pharmacol Sci,
29,
250-257.
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J.Plati,
O.Bucur,
and
R.Khosravi-Far
(2008).
Dysregulation of apoptotic signaling in cancer: molecular mechanisms and therapeutic opportunities.
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J Cell Biochem,
104,
1124-1149.
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J.W.Huang,
Z.Zhang,
B.Wu,
J.F.Cellitti,
X.Zhang,
R.Dahl,
C.W.Shiau,
K.Welsh,
A.Emdadi,
J.L.Stebbins,
J.C.Reed,
and
M.Pellecchia
(2008).
Fragment-based design of small molecule X-linked inhibitor of apoptosis protein inhibitors.
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J Med Chem,
51,
7111-7118.
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K.Sekine,
K.Takubo,
R.Kikuchi,
M.Nishimoto,
M.Kitagawa,
F.Abe,
K.Nishikawa,
T.Tsuruo,
and
M.Naito
(2008).
Small molecules destabilize cIAP1 by activating auto-ubiquitylation.
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J Biol Chem,
283,
8961-8968.
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L.L.Chan,
M.Pineda,
J.T.Heeres,
P.J.Hergenrother,
and
B.T.Cunningham
(2008).
A general method for discovering inhibitors of protein-DNA interactions using photonic crystal biosensors.
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ACS Chem Biol,
3,
437-448.
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L.Schyschka,
A.Rudy,
I.Jeremias,
N.Barth,
G.R.Pettit,
and
A.M.Vollmar
(2008).
Spongistatin 1: a new chemosensitizing marine compound that degrades XIAP.
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Leukemia,
22,
1737-1745.
|
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M.Lakshmanan,
U.Bughani,
S.Duraisamy,
M.Diwan,
S.Dastidar,
and
A.Ray
(2008).
Molecular targeting of E3 ligases--a therapeutic approach for cancer.
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Expert Opin Ther Targets,
12,
855-870.
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R.Hamacher,
R.M.Schmid,
D.Saur,
and
G.Schneider
(2008).
Apoptotic pathways in pancreatic ductal adenocarcinoma.
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Mol Cancer,
7,
64.
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S.M.Langemeijer,
A.O.de Graaf,
and
J.H.Jansen
(2008).
IAPs as therapeutic targets in haematological malignancies.
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Expert Opin Ther Targets,
12,
981-993.
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V.N.Uversky,
C.J.Oldfield,
and
A.K.Dunker
(2008).
Intrinsically disordered proteins in human diseases: introducing the D2 concept.
|
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Annu Rev Biophys,
37,
215-246.
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W.Qi,
K.Shakalya,
A.Stejskal,
A.Goldman,
S.Beeck,
L.Cooke,
and
D.Mahadevan
(2008).
NSC348884, a nucleophosmin inhibitor disrupts oligomer formation and induces apoptosis in human cancer cells.
|
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Oncogene,
27,
4210-4220.
|
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Y.Peng,
H.Sun,
Z.Nikolovska-Coleska,
S.Qiu,
C.Y.Yang,
J.Lu,
Q.Cai,
H.Yi,
S.Kang,
D.Yang,
and
S.Wang
(2008).
Potent, orally bioavailable diazabicyclic small-molecule mimetics of second mitochondria-derived activator of caspases.
|
| |
J Med Chem,
51,
8158-8162.
|
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Z.Nikolovska-Coleska,
J.L.Meagher,
S.Jiang,
C.Y.Yang,
S.Qiu,
P.P.Roller,
J.A.Stuckey,
and
S.Wang
(2008).
Interaction of a cyclic, bivalent smac mimetic with the x-linked inhibitor of apoptosis protein.
|
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Biochemistry,
47,
9811-9824.
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PDB code:
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A.Kurakin,
and
D.E.Bredesen
(2007).
An unconventional IAP-binding motif revealed by target-assisted iterative screening (TAIS) of the BIR3-cIAP1 domain.
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| |
J Mol Recognit,
20,
39-50.
|
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A.M.Hunter,
E.C.LaCasse,
and
R.G.Korneluk
(2007).
The inhibitors of apoptosis (IAPs) as cancer targets.
|
| |
Apoptosis,
12,
1543-1568.
|
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D.Chauhan,
P.Neri,
M.Velankar,
K.Podar,
T.Hideshima,
M.Fulciniti,
P.Tassone,
N.Raje,
C.Mitsiades,
N.Mitsiades,
P.Richardson,
L.Zawel,
M.Tran,
N.Munshi,
and
K.C.Anderson
(2007).
Targeting mitochondrial factor Smac/DIABLO as therapy for multiple myeloma (MM).
|
| |
Blood,
109,
1220-1227.
|
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E.J.Dean,
M.Ranson,
F.Blackhall,
and
C.Dive
(2007).
X-linked inhibitor of apoptosis protein as a therapeutic target.
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Expert Opin Ther Targets,
11,
1459-1471.
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H.Sun,
Z.Nikolovska-Coleska,
J.Lu,
J.L.Meagher,
C.Y.Yang,
S.Qiu,
Y.Tomita,
Y.Ueda,
S.Jiang,
K.Krajewski,
P.P.Roller,
J.A.Stuckey,
and
S.Wang
(2007).
Design, synthesis, and characterization of a potent, nonpeptide, cell-permeable, bivalent Smac mimetic that concurrently targets both the BIR2 and BIR3 domains in XIAP.
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J Am Chem Soc,
129,
15279-15294.
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S.Fulda
(2007).
Inhibitor of apoptosis proteins as targets for anticancer therapy.
|
| |
Expert Rev Anticancer Ther,
7,
1255-1264.
|
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S.Giagkousiklidis,
S.H.Vellanki,
K.M.Debatin,
and
S.Fulda
(2007).
Sensitization of pancreatic carcinoma cells for gamma-irradiation-induced apoptosis by XIAP inhibition.
|
| |
Oncogene,
26,
7006-7016.
|
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U.Fischer,
K.Janssen,
and
K.Schulze-Osthoff
(2007).
Cutting-edge apoptosis-based therapeutics: a panacea for cancer?
|
| |
BioDrugs,
21,
273-297.
|
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A.D.Schimmer,
S.Dalili,
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The most recent references are shown first.
Citation data come partly from CiteXplore and partly
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only a partial list as not all journals are covered by
either method. However, we are continually building up the citation data
so more and more references will be included with time.
Where a reference describes a PDB structure, the PDB
codes are
shown on the right.
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