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PDBsum entry 1d12
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DOI no:
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Biochemistry
29:2538-2549
(1990)
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PubMed id:
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Structural comparison of anticancer drug-DNA complexes: adriamycin and daunomycin.
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C.A.Frederick,
L.D.Williams,
G.Ughetto,
G.A.van der Marel,
J.H.van Boom,
A.Rich,
A.H.Wang.
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ABSTRACT
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The anticancer drugs adriamycin and daunomycin have each been crystallized with
the DNA sequence d(CGATCG) and the three-dimensional structures of the complexes
solved at 1.7- and 1.5-A resolution, respectively. These antitumor drugs have
significantly different clinical properties, yet they differ chemically by only
the additional hydroxyl at C14 of adriamycin. In these complexes the chromophore
is intercalated at the CpG steps at either end of the DNA helix with the amino
sugar extended into the minor groove. Solution of the structure of daunomycin
bound to d(CGATCG) has made it possible to compare it with the previously
reported structure of daunomycin bound to d(CGTACG). Although the two daunomycin
complexes are similar, there is an interesting sequence dependence of the
binding of the amino sugar to the A-T base pair outside the intercalation site.
The complex of daunomycin with d(CGATCG) has tighter binding than the complex
with d(CGTACG), leading us to infer a sequence preference in the binding of this
anthracycline drug. The structures of daunomycin and adriamycin with d(CGATCG)
are very similar. However, there are additional solvent interactions with the
adriamycin C14 hydroxyl linking it to the DNA. Surprisingly, under the influence
of the altered solvation, there is considerable difference in the conformation
of spermine in these two complexes. The observed changes in the overall
structures of the ternary complexes amplify the small chemical differences
between these two antibiotics and provide a possible explanation for the
significantly different clinical activities of these important drugs.
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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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|
 |
C.Lu,
M.M.Xing,
and
W.Zhong
(2011).
Shell cross-linked and hepatocyte-targeting nanoparticles containing doxorubicin via acid-cleavable linkage.
|
| |
Nanomedicine,
7,
80-87.
|
 |
|
|
|
|
 |
I.Manet,
F.Manoli,
B.Zambelli,
G.Andreano,
A.Masi,
L.Cellai,
and
S.Monti
(2011).
Affinity of the anthracycline antitumor drugs Doxorubicin and Sabarubicin for human telomeric G-quadruplex structures.
|
| |
Phys Chem Chem Phys,
13,
540-551.
|
 |
|
|
|
|
 |
M.Z.Akhter,
A.Sharma,
and
M.R.Rajeswari
(2011).
Interaction of adriamycin with a promoter region of hmga1 and its inhibitory effect on HMGA1 expression in A431 human squamous carcinoma cell line.
|
| |
Mol Biosyst,
7,
1336-1346.
|
 |
|
|
|
|
 |
C.A.Mitsopoulou,
and
C.Dagas
(2010).
Synthesis, Characterization, DNA Binding, and Photocleavage Activity of Oxorhenium (V) Complexes with alpha-Diimine and Quinoxaline Ligands.
|
| |
Bioinorg Chem Appl,
(),
973742.
|
 |
|
|
|
|
 |
M.Shin,
H.Matsunaga,
and
K.Fujiwara
(2010).
Differences in accumulation of anthracyclines daunorubicin, doxorubicin and epirubicin in rat tissues revealed by immunocytochemistry.
|
| |
Histochem Cell Biol,
133,
677-682.
|
 |
|
|
|
|
 |
P.H.Lin,
Y.H.Kao,
Y.Chang,
Y.C.Cheng,
C.C.Chien,
and
W.Y.Chen
(2010).
Daunomycin interaction with DNA: microcalorimetric studies of the thermodynamics and binding mechanism.
|
| |
Biotechnol J,
5,
1069-1077.
|
 |
|
|
|
|
 |
R.J.Marcheschi,
K.D.Mouzakis,
and
S.E.Butcher
(2009).
Selection and characterization of small molecules that bind the HIV-1 frameshift site RNA.
|
| |
ACS Chem Biol,
4,
844-854.
|
 |
|
|
|
|
 |
V.V.Kostjukov,
N.M.Khomytova,
and
M.P.Evstigneev
(2009).
Partition of thermodynamic energies of drug-DNA complexation.
|
| |
Biopolymers,
91,
773-790.
|
 |
|
|
|
|
 |
H.Yu,
J.Ren,
J.B.Chaires,
and
X.Qu
(2008).
Hydration of drug-DNA complexes: greater water uptake for adriamycin compared to daunomycin.
|
| |
J Med Chem,
51,
5909-5911.
|
 |
|
|
|
|
 |
J.B.Chaires
(2008).
Calorimetry and thermodynamics in drug design.
|
| |
Annu Rev Biophys,
37,
135-151.
|
 |
|
|
|
|
 |
V.V.Kostjukov,
N.M.Khomytova,
D.B.Davies,
and
M.P.Evstigneev
(2008).
Electrostatic contribution to the energy of binding of aromatic ligands with DNA.
|
| |
Biopolymers,
89,
680-690.
|
 |
|
|
|
|
 |
C.Leimkuhler,
M.Fridman,
T.Lupoli,
S.Walker,
C.T.Walsh,
and
D.Kahne
(2007).
Characterization of rhodosaminyl transfer by the AknS/AknT glycosylation complex and its use in reconstituting the biosynthetic pathway of aclacinomycin A.
|
| |
J Am Chem Soc,
129,
10546-10550.
|
 |
|
|
|
|
 |
C.M.Baker,
and
G.H.Grant
(2007).
Role of aromatic amino acids in protein-nucleic acid recognition.
|
| |
Biopolymers,
85,
456-470.
|
 |
|
|
|
|
 |
F.Rosu,
C.H.Nguyen,
E.De Pauw,
and
V.Gabelica
(2007).
Ligand binding mode to duplex and triplex DNA assessed by combining electrospray tandem mass spectrometry and molecular modeling.
|
| |
J Am Soc Mass Spectrom,
18,
1052-1062.
|
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|
|
|
|
 |
J.P.Mattila,
K.Sabatini,
and
P.K.Kinnunen
(2007).
Oxidized phospholipids as potential novel drug targets.
|
| |
Biophys J,
93,
3105-3112.
|
 |
|
|
|
|
 |
M.J.Hannon
(2007).
Supramolecular DNA recognition.
|
| |
Chem Soc Rev,
36,
280-295.
|
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|
|
|
|
 |
S.Komorsky-Lovrić
(2006).
Redox kinetics of adriamycin adsorbed on the surface of graphite and mercury electrodes.
|
| |
Bioelectrochemistry,
69,
82-87.
|
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|
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|
 |
S.Napoli,
U.Negri,
F.Arcamone,
M.L.Capobianco,
G.M.Carbone,
and
C.V.Catapano
(2006).
Growth inhibition and apoptosis induced by daunomycin-conjugated triplex-forming oligonucleotides targeting the c-myc gene in prostate cancer cells.
|
| |
Nucleic Acids Res,
34,
734-744.
|
 |
|
|
|
|
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V.Bagalkot,
O.C.Farokhzad,
R.Langer,
and
S.Jon
(2006).
An aptamer-doxorubicin physical conjugate as a novel targeted drug-delivery platform.
|
| |
Angew Chem Int Ed Engl,
45,
8149-8152.
|
 |
|
|
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|
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J.Chen,
D.Du,
F.Yan,
H.X.Ju,
and
H.Z.Lian
(2005).
Electrochemical antitumor drug sensitivity test for leukemia K562 cells at a carbon-nanotube-modified electrode.
|
| |
Chemistry,
11,
1467-1472.
|
 |
|
|
|
|
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J.Portugal,
D.J.Cashman,
J.O.Trent,
N.Ferrer-Miralles,
T.Przewloka,
I.Fokt,
W.Priebe,
and
J.B.Chaires
(2005).
A new bisintercalating anthracycline with picomolar DNA binding affinity.
|
| |
J Med Chem,
48,
8209-8219.
|
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|
|
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|
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W.Lu,
C.Leimkuhler,
G.J.Gatto,
R.G.Kruger,
M.Oberthür,
D.Kahne,
and
C.T.Walsh
(2005).
AknT is an activating protein for the glycosyltransferase AknS in L-aminodeoxysugar transfer to the aglycone of aclacinomycin A.
|
| |
Chem Biol,
12,
527-534.
|
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|
|
|
|
 |
G.M.Carbone,
E.McGuffie,
S.Napoli,
C.E.Flanagan,
C.Dembech,
U.Negri,
F.Arcamone,
M.L.Capobianco,
and
C.V.Catapano
(2004).
DNA binding and antigene activity of a daunomycin-conjugated triplex-forming oligonucleotide targeting the P2 promoter of the human c-myc gene.
|
| |
Nucleic Acids Res,
32,
2396-2410.
|
 |
|
|
|
|
 |
K.R.Fox,
R.Webster,
R.J.Phelps,
I.Fokt,
and
W.Priebe
(2004).
Sequence selective binding of bis-daunorubicin WP631 to DNA.
|
| |
Eur J Biochem,
271,
3556-3566.
|
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|
|
|
|
 |
M.Trieb,
C.Rauch,
F.R.Wibowo,
B.Wellenzohn,
and
K.R.Liedl
(2004).
Cooperative effects on the formation of intercalation sites.
|
| |
Nucleic Acids Res,
32,
4696-4703.
|
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|
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|
|
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C.Temperini,
L.Messori,
P.Orioli,
C.Di Bugno,
F.Animati,
and
G.Ughetto
(2003).
The crystal structure of the complex between a disaccharide anthracycline and the DNA hexamer d(CGATCG) reveals two different binding sites involving two DNA duplexes.
|
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Nucleic Acids Res,
31,
1464-1469.
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PDB code:
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D.J.Cashman,
J.N.Scarsdale,
and
G.E.Kellogg
(2003).
Hydropathic analysis of the free energy differences in anthracycline antibiotic binding to DNA.
|
| |
Nucleic Acids Res,
31,
4410-4416.
|
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|
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|
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K.Shi,
B.Pan,
and
M.Sundaralingam
(2003).
Structure of a B-form DNA/RNA chimera (dC)(rG)d(ATCG) complexed with daunomycin at 1.5 A resolution.
|
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Acta Crystallogr D Biol Crystallogr,
59,
1377-1383.
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PDB code:
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L.J.Ming
(2003).
Structure and function of "metalloantibiotics".
|
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Med Res Rev,
23,
697-762.
|
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|
|
|
|
 |
S.B.Howerton,
A.Nagpal,
and
L.D.Williams
(2003).
Surprising roles of electrostatic interactions in DNA-ligand complexes.
|
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Biopolymers,
69,
87-99.
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PDB code:
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S.Villamarín,
S.Mansilla,
N.Ferrer-Miralles,
W.Priebe,
and
J.Portugal
(2003).
A comparative analysis of the time-dependent antiproliferative effects of daunorubicin and WP631.
|
| |
Eur J Biochem,
270,
764-770.
|
 |
|
|
|
|
 |
X.Qu,
J.Ren,
P.V.Riccelli,
A.S.Benight,
and
J.B.Chaires
(2003).
Enthalpy/entropy compensation: influence of DNA flanking sequence on the binding of 7-amino actinomycin D to its primary binding site in short DNA duplexes.
|
| |
Biochemistry,
42,
11960-11967.
|
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|
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J.N.Lisgarten,
M.Coll,
J.Portugal,
C.W.Wright,
and
J.Aymami
(2002).
The antimalarial and cytotoxic drug cryptolepine intercalates into DNA at cytosine-cytosine sites.
|
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Nat Struct Biol,
9,
57-60.
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PDB code:
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F.Zunino,
G.Pratesi,
and
P.Perego
(2001).
Role of the sugar moiety in the pharmacological activity of anthracyclines: development of a novel series of disaccharide analogs.
|
| |
Biochem Pharmacol,
61,
933-938.
|
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|
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G.Z.Jin,
Y.J.You,
Y.Kim,
N.H.Nam,
and
B.Z.Ahn
(2001).
Esters of chlorambucil with 2-substituted 1,4-dihydroxy-9,10-anthraquinones as multifunctional anticancer agents.
|
| |
Eur J Med Chem,
36,
361-366.
|
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|
|
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|
 |
X.Qu,
C.Wan,
H.C.Becker,
D.Zhong,
and
A.H.Zewail
(2001).
The anticancer drug-DNA complex: femtosecond primary dynamics for anthracycline antibiotics function.
|
| |
Proc Natl Acad Sci U S A,
98,
14212-14217.
|
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|
|
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|
 |
M.N.Tam,
N.H.Nam,
G.Z.Jin,
G.Y.Song,
and
B.Z.Ahn
(2000).
Synthesis and evaluation of the antitumor activity of 2-substituted 1,4-dihydroxy-9,10-anthraquinones.
|
| |
Arch Pharm (Weinheim),
333,
189-194.
|
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P.Saminadin,
A.Dautant,
M.Mondon,
B.Langlois D'estaintot,
C.Courseille,
and
G.Précigoux
(2000).
Release of the cyano moiety in the crystal structure of N-cyanomethyl-N-(2-methoxyethyl)-daunomycin complexed with d(CGATCG).
|
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Eur J Biochem,
267,
457-464.
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PDB code:
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Y.Razskazovskiy,
M.G.Debije,
and
W.A.Bernhard
(2000).
Direct radiation damage to crystalline DNA: what is the source of unaltered base release?
|
| |
Radiat Res,
153,
436-441.
|
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|
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|
 |
A.Adams,
J.M.Guss,
C.A.Collyer,
W.A.Denny,
and
L.P.Wakelin
(1999).
Crystal structure of the topoisomerase II poison 9-amino-[N-(2-dimethylamino)ethyl]acridine-4-carboxamide bound to the DNA hexanucleotide d(CGTACG)2.
|
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Biochemistry,
38,
9221-9233.
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PDB code:
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K.Nakai,
Y.Takagi,
S.Ogawa,
and
T.Tsuchiya
(1999).
Synthesis and antitumor activity of 5'-demethyl-5'-trifluoromethyl-daunorubicin and -doxorubicin.
|
| |
Carbohydr Res,
320,
8.
|
 |
|
|
|
|
 |
S.D.Cline,
W.R.Jones,
M.P.Stone,
and
N.Osheroff
(1999).
DNA abasic lesions in a different light: solution structure of an endogenous topoisomerase II poison.
|
| |
Biochemistry,
38,
15500-15507.
|
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|
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|
 |
S.Majee,
and
A.Chakrabarti
(1999).
Membrane interaction of an antitumor antibiotic, mithramycin, with anionic phospholipid vesicles.
|
| |
Biochem Pharmacol,
57,
981-987.
|
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|
 |
G.Z.Jin,
G.Y.Song,
X.G.Zheng,
Y.Kim,
D.E.Sok,
and
B.Z.Ahn
(1998).
2-(1-Oxyalkyl)-1,4-dioxy-9,10-anthraquinones: synthesis and evaluation of antitumor activity.
|
| |
Arch Pharm Res,
21,
198-206.
|
 |
|
|
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|
 |
S.M.Zeman,
K.M.Depew,
S.J.Danishefsky,
and
D.M.Crothers
(1998).
Simultaneous determination of helical unwinding angles and intrinsic association constants in ligand-DNA complexes: the interaction between DNA and calichearubicin B.
|
| |
Proc Natl Acad Sci U S A,
95,
4327-4332.
|
 |
|
|
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|
 |
S.Y.Chiang,
J.C.Azizkhan,
and
T.A.Beerman
(1998).
A comparison of DNA-binding drugs as inhibitors of E2F1- and Sp1-DNA complexes and associated gene expression.
|
| |
Biochemistry,
37,
3109-3115.
|
 |
|
|
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|
 |
X.Shui,
L.McFail-Isom,
G.G.Hu,
and
L.D.Williams
(1998).
The B-DNA dodecamer at high resolution reveals a spine of water on sodium.
|
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Biochemistry,
37,
8341-8355.
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PDB code:
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A.Garbesi,
S.Bonazzi,
S.Zanella,
M.L.Capobianco,
G.Giannini,
and
F.Arcamone
(1997).
Synthesis and binding properties of conjugates between oligodeoxynucleotides and daunorubicin derivatives.
|
| |
Nucleic Acids Res,
25,
2121-2128.
|
 |
|
|
|
|
 |
D.Suh,
and
L.F.Povirk
(1997).
Mapping of the cleavage-associated bleomycin binding site on DNA with a new method based on site-specific blockage of the minor groove with N2-isobutyrylguanine.
|
| |
Biochemistry,
36,
4248-4257.
|
 |
|
|
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|
 |
C.J.Shelton,
M.M.Harding,
and
A.S.Prakash
(1996).
Enzymatic and chemical footprinting of anthracycline antitumor antibiotics and related saccharide side chains.
|
| |
Biochemistry,
35,
7974-7982.
|
 |
|
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|
 |
J.E.Coury,
L.McFail-Isom,
L.D.Williams,
and
L.A.Bottomley
(1996).
A novel assay for drug-DNA binding mode, affinity, and exclusion number: scanning force microscopy.
|
| |
Proc Natl Acad Sci U S A,
93,
12283-12286.
|
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|
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|
 |
L.A.Lipscomb,
F.X.Zhou,
S.R.Presnell,
R.J.Woo,
M.E.Peek,
R.R.Plaskon,
and
L.D.Williams
(1996).
Structure of DNA-porphyrin complex.
|
| |
Biochemistry,
35,
2818-2823.
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PDB code:
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R.Barthwal,
A.Mujeeb,
N.Srivastava,
and
U.Sharma
(1996).
A proton nuclear magnetic resonance investigation of the conformation of daunomycin.
|
| |
Chem Biol Interact,
100,
125-139.
|
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|
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W.B.Cruse,
P.Saludjian,
Y.Leroux,
G.Léger,
D.E.Manouni,
and
T.Prangé
(1996).
A continuous transition from A-DNA to B-DNA in the 1:1 complex between nogalamycin and the hexamer dCCCGGG.
|
| |
J Biol Chem,
271,
15558-15567.
|
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PDB code:
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Y.Yoshikawa,
K.Yoshikawa,
and
T.Kanbe
(1996).
Daunomycin unfolds compactly packed DNA.
|
| |
Biophys Chem,
61,
93.
|
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|
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|
 |
C.Alhambra,
F.J.Luque,
J.Portugal,
and
M.Orozco
(1995).
Molecular dynamics study of the binding of elsamicin A to DNA.
|
| |
Eur J Biochem,
230,
555-566.
|
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|
|
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|
 |
G.A.Marsch,
D.E.Graves,
and
R.L.Rill
(1995).
Photoaffinity approaches to determining the sequence selectivities of DNA-small molecule interactions: actinomycin D and ethidium.
|
| |
Nucleic Acids Res,
23,
1252-1259.
|
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|
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I.Berger,
L.Su,
J.R.Spitzner,
C.Kang,
T.G.Burke,
and
A.Rich
(1995).
Molecular structure of the halogenated anti-cancer drug iododoxorubicin complexed with d(TGTACA) and d(CGATCG).
|
| |
Nucleic Acids Res,
23,
4488-4494.
|
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PDB codes:
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P.F.Gallet,
A.Maftah,
J.M.Petit,
M.Denis-Gay,
and
R.Julien
(1995).
Direct cardiolipin assay in yeast using the red fluorescence emission of 10-N-nonyl acridine orange.
|
| |
Eur J Biochem,
228,
113-119.
|
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|
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|
 |
C.Ban,
B.Ramakrishnan,
and
M.Sundaralingam
(1994).
Crystal structure of the highly distorted chimeric decamer r(C)d(CGGCGCCG)r(G).spermine complex--spermine binding to phosphate only and minor groove tertiary base-pairing.
|
| |
Nucleic Acids Res,
22,
5466-5476.
|
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PDB code:
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P.D.Grootenhuis,
D.C.Roe,
P.A.Kollman,
and
I.D.Kuntz
(1994).
Finding potential DNA-binding compounds by using molecular shape.
|
| |
J Comput Aided Mol Des,
8,
731-750.
|
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|
|
|
|
 |
H.R.Matthews,
and
H.R.Matthews
(1993).
Polyamines, chromatin structure and transcription.
|
| |
Bioessays,
15,
561-566.
|
 |
|
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|
 |
A.Párraga,
and
J.Portugal
(1992).
Detection of elsamicin-DNA binding specificity by restriction enzyme cleavage.
|
| |
FEBS Lett,
300,
25-29.
|
 |
|
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|
 |
B.Langlois d'Estaintot,
B.Gallois,
T.Brown,
and
W.N.Hunter
(1992).
The molecular structure of a 4'-epiadriamycin complex with d(TGATCA) at 1.7A resolution: comparison with the structure of 4'-epiadriamycin d(TGTACA) and d(CGATCG) complexes.
|
| |
Nucleic Acids Res,
20,
3561-3566.
|
 |
|
PDB code:
|
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|
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|
 |
C.Bailly,
J.P.Hénichart,
P.Colson,
and
C.Houssier
(1992).
Drug-DNA sequence-dependent interactions analysed by electric linear dichroism.
|
| |
J Mol Recognit,
5,
155-171.
|
 |
|
|
|
|
 |
G.A.Leonard,
T.Brown,
and
W.N.Hunter
(1992).
Anthracycline binding to DNA. High-resolution structure of d(TGTACA) complexed with 4'-epiadriamycin.
|
| |
Eur J Biochem,
204,
69-74.
|
 |
|
PDB code:
|
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|
|
|
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|
 |
M.Lu,
Q.Guo,
and
N.R.Kallenbach
(1992).
Interaction of drugs with branched DNA structures.
|
| |
Crit Rev Biochem Mol Biol,
27,
157-190.
|
 |
|
|
|
|
 |
M.Monnot,
O.Mauffret,
E.Lescot,
and
S.Fermandjian
(1992).
Probing intercalation and conformational effects of the anticancer drug 2-methyl-9-hydroxyellipticinium acetate in DNA fragments with circular dichroism.
|
| |
Eur J Biochem,
204,
1035-1039.
|
 |
|
|
|
|
 |
R.A.Friedman,
and
B.Honig
(1992).
The electrostatic contribution to DNA base-stacking interactions.
|
| |
Biopolymers,
32,
145-159.
|
 |
|
|
|
|
 |
B.G.Feuerstein,
L.D.Williams,
H.S.Basu,
and
L.J.Marton
(1991).
Implications and concepts of polyamine-nucleic acid interactions.
|
| |
J Cell Biochem,
46,
37-47.
|
 |
|
|
|
|
 |
Q.Gao,
L.D.Williams,
M.Egli,
D.Rabinovich,
S.L.Chen,
G.J.Quigley,
and
A.Rich
(1991).
Drug-induced DNA repair: X-ray structure of a DNA-ditercalinium complex.
|
| |
Proc Natl Acad Sci U S A,
88,
2422-2426.
|
 |
|
PDB code:
|
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 |
Y.G.Gao,
Y.C.Liaw,
Y.K.Li,
G.A.van der Marel,
J.H.van Boom,
and
A.H.Wang
(1991).
Facile formation of a crosslinked adduct between DNA and the daunorubicin derivative MAR70 mediated by formaldehyde: molecular structure of the MAR70-d(CGTnACG) covalent adduct.
|
| |
Proc Natl Acad Sci U S A,
88,
4845-4849.
|
 |
|
PDB codes:
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 |
G.Capranico,
K.W.Kohn,
and
Y.Pommier
(1990).
Local sequence requirements for DNA cleavage by mammalian topoisomerase II in the presence of doxorubicin.
|
| |
Nucleic Acids Res,
18,
6611-6619.
|
 |
|
|
|
|
 |
L.D.Williams,
C.A.Frederick,
G.Ughetto,
and
A.Rich
(1990).
Ternary interactions of spermine with DNA: 4'-epiadriamycin and other DNA: anthracycline complexes.
|
| |
Nucleic Acids Res,
18,
5533-5541.
|
 |
|
PDB code:
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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
code is
shown on the right.
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}
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