Publications

Wake Forest Papers

F. Liu, J. Suryadi and U. Bierbach: Cellular Recognition and Repair of Monofunctional-Intercalative Platinum-DNA Adducts. Chemical Research in Toxicology, 28(11), 2170-2178 (2015)

DOI: 10.1021/acs.chemrestox.5b00327

P. K. Langston, M. Yang, U. Bierbach, D. Parsonage, L. B. Poole, M. J. Price and J. M. Grayson: Au-ACRAMTU-PEt3 Alters Redox Balance To Inhibit T Cell Proliferation and Function. The Journal of Immunology, 195, 1984-1994 (2015)
DOI: 10.4049/jimmunol.1400391

S. Ding, U. Bierbach: Target-selective delivery and activation of platinum-based anticancer agents. Future Medicinal Chemistry, 7, 911-927. (2015)
DOI: 10.4155/fmc.15.37


M. Yang, A. J. Pickard, X. Qiao, M. J. Gueble, C. S. Day, G. L. Kucera, and U. Bierbach: Synthesis, Reactivity, and Biological Activity of Gold(I) Complexes Modified with Thiourea-Functionalized Tyrosine Kinase Inhibitors. Inorganic Chemistry, 54, 3316–3324. (2015)
DOI: 10.1021/ic502998a

A. J. Pickard, F. Liu, T. F. Bartenstein, L. G. Haines, K. E. Levine, G. L. Kucera, U. Bierbach: Redesigning the DNA-Targeted Chromophore in Platinum–Acridine Anticancer Agents: A Structure–Activity Relationship Study. Chemistry - A European Journal, 20, 16174-16187. (2014)
DOI: 10.1002/chem.201404845

S. Ding, A. J. Pickard, G. L. Kucera, U. Bierbach: Design of Enzymatically Cleavable Prodrugs of a Potent Platinum-Containing Anticancer Agent.Chemistry - A European Journal, 20, 16164-16173. (2014)
DOI: 10.1002/chem.201404675

X. Qiao, S. Ding, F. Liu, G. L. Kucera, U. Bierbach: Investigating the cellular fate of a DNA-targeted platinum-based anticancer agent by orthogonal double-click chemistry. Journal of Biological Inorganic Chemistry, 19, 415-426. (2014)
DOI: 10.1007/s00775-013-1086-1


A. J. Pickard, U. Bierbach: The Cell’s Nucleolus: an Emerging Target for Chemotherapeutic Intervention. ChemMedChem, 8, 1441-1449. (2013)
DOI: 10.1002/cmdc.201300262


S. Dutta, M. J. Snyder, D. Rosile, K. L. Binz, E. H. Roll, J. Suryadi, U. Bierbach, M. Guthold: PT-ACRAMTU, A Platinum–Acridine Anticancer Agent, Lengthens and Aggregates, but does not Stiffen or Soften DNA. Cell Biochemistry and Biophysics, 67, 1103-1113. (2013)
DOI: 10.1007/s12013-013-9614-8


S. Ding, X. Qiao, J. Suryadi, G. S. Marrs, G. L. Kucera, U. Bierbach: Using Fluorescent Post-Labeling To Probe the Subcellular Localization of DNA-Targeted Platinum Anticancer Agents. Angewandte Chemie, 52, 3350-3354. (2013)
DOI: 10.1002/anie.201210079


S. Ding, X. Qiao, G. L. Kucera, U. Bierbach: Design of a platinum–acridine–endoxifen conjugate targeted at hormone-dependent breast cancer. Chemical Communications, 49, 2415-2417. (2013)
DOI: 10.1039/C3CC38957J


S. Ding, X. Qiao, G. L. Kucera, U. Bierbach: Using a Build-and-Click Approach for Producing Structural and Functional Diversity in DNA-Targeted Hybrid Anticancer Agents. Journal of Medicinal Chemistry, 55, 10198-10203. (2012)
DOI: 10.1021/jm301278c

J. Suryadi, U. Bierbach: DNA Metalating-Intercalating Hybrid Agents for the Treatment of Chemoresistant Cancers. Chemistry - A European Journal, 18, 12926-12934. (2012)
DOI: 10.1002/chem.201202050

K. Cheung-Ong, K. T. Song, Z. Ma, D. Shabtai, A. Y. Lee, D. Gallo, L. E. Heisler, G. W. Brown, U. Bierbach, G. Giaever, C. Nislow: Comparative Chemogenomics To Examine the Mechanism of Action of DNA-Targeted Platinum-Acridine Anticancer Agents. ACS Chemical Biology, 7, 1892-1901. (2012)
DOI: 10.1021/cb300320d

L. A. Graham, J. Suryadi, T. K. West, G. L. Kucera, U. Bierbach: Synthesis, Aqueous Reactivity, and Biological Evalulation of Carboxylic Acid Ester-Functionalized Platinum-Acridine Hybrid Anticancer Agents. Journal of Medicinal Chemistry, 55, 7817-7827. (2012)
DOI: 10.1021/jm300879k


X. Qiao, A. E. Zeitany, M. W. Wright, A. S. Essader, K. E. Levine, U. Bierbach: Analysis of the DNA damage produced by a platinum–acridine antitumor agent and its effects in NCI-H460 lung cancer cells. Metallomics, 4, 645-652. (2012)
DOI: 10.1039/C2MT20031G

L. Rao, J. D. Dworkin, W. E. Nell, U. Bierbach: Interactions of Platinum-Modified Perylene Derivative with the Human Telomeric G-Quadruplex. Journal of Physical Chemistry B, 115, 13701-13712. (2011)
DOI: 10.1021/jp207265s

C. L. Smyre, G. Saluta, T. E. Kute, G. L. Kucera, U. Bierbach: Inhibition of DNA Synthesis by a Platinum–Acridine Hybrid Agent Leads to Potent Cell Kill in Non-Small Cell Lung Cancer. ACS Medicinal Chemistry Letters, 2, 870-874. (2011)
DOI: 10.1021/ml2001888

H. Kostrhunova, J. Malina, A. J. Pickard, J. Stepankova, M. Vojtiskova, J. Kasparkova, T. Muchova, M. L. Rohlfing, U. Bierbach, V. Brabec: Replacement of a Thiourea with an Amidine Group in a Monofunctional Platinum–Acridine Antitumor Agent. Effect on DNA Interactions, DNA Adduct Recognition and Repair. Molecular Pharmaceutics, 8, 1941-1954. (2011)
DOI: 10.1021/mp200309x

L. A. Graham, G. M. Wilson, T. K. West, C. S. Day, G. L. Kucera, U. Bierbach: Unusual Reactivity of a Potent Platinum-Acridine Hybrid Antitumor Agent. ACS Medicinal Chemistry Letters, 2, 687-691. (2011)
DOI: 10.1021/ml200104h

J. R. Choudhury, L. Rao, U. Bierbach: Rates of intercalator-driven platination of DNA determined by restriction enzyme cleavage inhibition assay. Journal of Biological Inorganic Chemistry, 16, 373-380. (2011).
DOI: 10.1007/s00775-010-0733-z

L. Rao, T. K. West, G. Saluta, G. L. Kucera, U. Bierbach: Probing Platinum-Adenine-N3 Adduct Formation with DNA Minor-Groove Binding Agents. Chemical Research in Toxicology, 23, 1148-1150. (2010).
DOI: 10.1021/tx100170p

L. C. Eiter, N. W. Hall, C. S. Day, G. Saluta, G. L. Kucera, U. Bierbach: Gold(I) Analogues of a Platinum-Acridine Antitumor Agent are Only Moderately Cytotoxic but Show Potent Activity against Mycobacterium tuberculosis. J. Med. Chem., 52, 6519-6522. (2009).
DOI: 10.1021/jm9012856

A. R. Kheradi, G. Saluta, G. L. Kucera, C. S. Day, U. Bierbach: Synthesis and biological evaluation of platinum-acridine hybrid agents modified with bipyridine non-leaving groups. Bioorg. Med. Chem. Lett., 19, 3423-3425. (2009).
DOI: 10.1016/j.bmcl.2009.05.046

Z. Ma, L. Rao, U. Bierbach: Replacement of a Thiourea-S with an Amidine-NH Donor Group in a Platinum-Acridine Antitumor Compound Reduces the Metal's Reactivity with Cysteine Sulfur. J. Med. Chem., 52, 3424-3427. (2009).
DOI: 10.1021/jm900451y

Z. Ma, J. Roy Choudhury, M. W. Wright, C. S. Day, G. Saluta, G. L. Kucera and U. Bierbach: A Non-Cross-Linking Platinum−Acridine Agent with Potent Activity in Non-Small-Cell Lung Cancer. J. Med. Chem., 51, 7574. (2008).
DOI: 10.1021/jm800900g


Z. Ma, G. Saluta, G. L. Kucera, and U. Bierbach: Effect of linkage geometry on biological activity in thiourea- and guanidine-substituted acridines and platinum–acridines. Bioorg. Med. Chem. Lett. 18, 3799. (2008).
DOI: 10.1016/j.bmcl.2008.05.043


J. Roy Choudhury, R.Guddneppanavar, G. Saluta, G. L. Kucera, and U. Bierbach: Tuning the DNA Conformational Perturbations Induced by Cytotoxic Platinum−Acridine Bisintercalators: Effect of Metal Cis/Trans Isomerism and DNA Threading Groups. J. Med. Chem., 51, 3069. (2008).
DOI: 10.1021/jm8003569

L.Rao and U.Bierbach: Kinetically Favored Platination of Adenine in the G-Rich Human Telomeric Repeat. J. Am. Chem. Soc., 129, 15764. (2007).
DOI: 10.1021/ja077390a

Z. Ma, C. S. Day and U. Bierbach: Unexpected Reactivity of the 9-Aminoacridine Chromophore in Guanidylation Reactions. J. Org. Chem., 72, 5387. (2007).
DOI: 10.1021/jo0705972

A. L. Smith, C. S. Day, L. Que Jr., Y. Zhou and U. Bierbach: Unexpected assembly of a novel triply bridged diiron(II) core by a bidentate Schiff base ligand. Inorg. Chim. Acta., 360, 2824. (2007).
DOI: 10.1016/j.ica.2007.01.001

R. Guddneppanavar, J. R. Choudhury, A. R. Kheradi, B. D. Steen, G. Saluta, G. L. Kucera, C. S. Day, and U. Bierbach: Effect of the Diamine Nonleaving Group in Platinum-Acridinylthiourea Conjugates on DNA Damage and Cytotoxicity. J. Med. Chem., 50, 2259. (2007).
DOI: 10.1021/jm0614376

R. Guddneppanavar and U. Bierbach: Adenine-N3 in the DNA Minor Groove - An Emerging Target for Platinum Containing Anticancer Pharmacophores. Anti-Cancer Agents in Medicinal Chemistry, 7, 125. (2007).
DOI: 10.2174/187152007779313991

R. Guddneppanavar, G. Saluta, G. L. Kucera, and U. Bierbach: Synthesis, Biological Activity, and DNA-Damage Profile of Platinum-Threading Intercalator Conjugates Designed To Target Adenine. J. Med. Chem., 49, 3204. (2006).
DOI: 10.1021/jm060035v

R. Guddneppanavar, M. W. Wright, A. K. Tomsey and U. Bierbach: Guanine Binding of a Cytotoxic Platinum-acridin-9-ylthiourea Conjugate Monitored by 1-D 1H and 2-D [1H, 15N] NMR Spectroscopy: Hydrolysis is not the Rate-determining Step. J. Inorg. Biochem. 100, 972. (2006).
DOI: 10.1016/j.jinorgbio.2005.12.021

J. Roy Choudhury, and U. Bierbach: Characterization of the Bisintercalative DNA Binding Mode of a Bifunctional Platinum -acridine Agent. Nucleic Acids Res. 33:5622 (2005).
DOI: 10.1093/nar/gki869

Y. Ma, C. S. Day, and U. Bierbach: Synthesis, Structure, and Reactivity of Monofunctional Platinum(II) and Palladium(II) Complexes Containing the Sterically Hindered Ligand 6-(methylpyridin-2-yl)acetate. J. Inorg. Biochem., 99, 2013(2005).
DOI: 10.1016/j.jinorgbio.2005.06.021

M. E. Budiman, U. Bierbach, and R. W. Alexander: Minor Groove Adducts Formed by a Platinum-acridine Conjugate Inhibit Association of TATA-binding Protein with its Cognate Sequence. Biochem., 44, 11262 (2005).
DOI: 10.1021/bi050745n

S. M. Hess, A. M. Mounce, R. C. Sequeira, T. M. Augustus, M. C. Ackley, and U. Bierbach: Platinum-Acridinylthiourea Conjugates Show Cell Line Specific Cytotoxic Enhancement in H460 Lung Carcinoma Cells Compared to Cisplatin. Cancer Chemother. Pharmacol., 56,337 (2005).
DOI: 10.1007/s00280-004-0987-7

H. Baruah, M. W. Wright, and U. Bierbach: Solution Structural Study of a DNA Duplex Containing the Guanine-N7 Adduct Formed by a Cytotoxic Platinum-Acridine Hybrid Agent. Biochemistry, 44, 6059-6070 (2005).
DOI: 10.1021/bi050021b

C. G. Barry, C. S. Day, and U. Bierbach: Duplex Promoted Platination of Adenine-N3 in the Minor Groove of DNA: Challenging a Longstanding Bioinorganic Paradigm. J. Am. Chem. Soc., 127, 1160-1169 (2005).
DOI: 10.1021/ja0451620

S. M. Hess, J. G. Anderson, and U. Bierbach: A Non-Crosslinking Platinum-Acridine Hybrid Agent Shows Enhanced Cytotoxicity Compared to Clinical BCNU and Cisplatin in Glioblastoma Cells. Bioorg. Med. Chem. Lett. 15, 443-446 (2005).
DOI: 10.1016/j.bmcl.2004.10.049

H. Baruah, C. G. Barry and U. Bierbach: Platinum-Intercalator Conjugates: From DNA-Targeted Cisplatin Derivatives to Adenine Binding Complexes as Potential Modulators of Gene Regulation. Curr. Topics Med. Chem. 4, 1537-1549 (2004).
DOI: 10.2174/1568026043387313

M. E. Budiman, R. W. Alexander and U. Bierbach: Unique Base-Step Recognition by a Platinum-Acridinylthiourea Conjugate Leads to a DNA Damage Profile Complementary to That of the Anticancer Drug Cisplatin. Biochemistry 43, 8560-8567 (2004).
DOI: 10.1021/bi049415d

M. C. Ackley, C. G. Barry, A. M. Mounce, M. C. Farmer, B.-E. Springer, C. S. Day, M. W. Wright, S. J. Berners-Price, S. M. Hess, U. Bierbach: Structure-activity relationships in platinum-acridinylthiourea conjugates: effect of the thiourea nonleaving group on drug stability, nucleobase affinity, and in vitro cytotoxicity. J. Biol. Inorg. Chem. 9, 453-461 (2004).
DOI: 10.1007/s00775-004-0541-4

H. Baruah, C. S. Day, M. W. Wright and U. Bierbach: Metal-intercalator-mediated self-association and one-dimensional aggregation in the structure of the excised major DNA adduct of a platinum-acridine agent. J. Am. Chem. Soc. 126, 4492-4493 (2004).
DOI: 10.1021/ja038592j

H. Baruah and U. Bierbach: Biophysical characterization and molecular modeling of the coordinative-intercalative DNA monoadduct of a platinum-acridinylthiourea agent in a site-specifically modified dodecamer. J. Biol. Inorg. Chem. 9, 335-344 (2004).
DOI: 10.1007/s00775-004-0534-3

C. G. Barry, H. Baruah and U. Bierbach: Unprecedented Monofunctional Metalation of Adenine Nucleobase in Guanine and Thymine Containing Dinucleotide Sequences by a Cytotoxic Platinum-Acridine Hybrid Agent. J. Am. Chem. Soc. 125, 9629-9637 (2003).
DOI: 10.1021/ja0351443

H. Baruah and U. Bierbach: Unusual intercalation of acridin-9-ylthiourea into the 5'-GA/TC DNA base step from the minor groove: Implications for the covalent DNA adduct profile of a novel platinum-intercalator conjugate. Nucleic Acids Res. 31, 4138-4146 (2003).
DOI: 10.1093/nar/gkg465

T. M. Augustus, J. Anderson, S. M. Hess, and U. Bierbach: Bis(acridinylthiourea)platinum(II) Complexes: Synthesis, DNA Affinity, and Biological Activity in Glioblastoma Cells. Bioorg. Med. Chem. Lett. 13, 855-858 (2003).
DOI: 10.1016/S0960-894X(02)01078-8

C. G. Barry, E. C. Turney, C. S. Day, G. Saluta, G. L. Kucera, and U. Bierbach: Thermally Inert Metal Ammines as Light-inducible DNA-targeted Agents. Synthesis, Photochemistry, and Photobiology of a Prototypical Rhodium(III)-Intercalator Conjugate. Inorg. Chem., 41, 7159-7169 (2002).
DOI: 10.1021/ic025744n

J. M. Brow, C. R. Pleatman and U. Bierbach: Cytotoxic Acridinylthiourea and its Platinum Conjugate Produce Enzyme-mediated DNA Strand Breaks. Bioorg. Med. Chem. Lett., 12, 2953-2955 (2002).
DOI: 10.1016/S0960-894X(02)00620-0

H. Baruah, C.L. Rector, S. M. Monnier and U. Bierbach: Mechanism of action of non-cisplatin type DNA-targeted platinum anticancer agents: DNA interactions of novel acridinylthioureas and their platinum conjugates. Biochem. Pharmacol., 64:191 (2002).
DOI: 10.1016/S0006-2952(02)01107-3

E. T. Martins, H. Baruah, J. Kramarczyk, G. Saluta, C. S. Day, G. L. Kucera and U. Bierbach: Design, synthesis and biological activity of a novel non-cisplatin-type platinum-acridine pharmacophore. J. Med. Chem., 44:4492 (2001).
DOI: 10.1021/jm010293m

 

VCU and LIC (NL) Papers (Postdoctoral)

D. A. Sartori, B. Miller, U. Bierbach and N. Farrell: Modulation of the chemical and biological properties of transplatinum complexes. Monofunctional trans platinum complexes containing one nucleobase as potential antiviral chemotypes. J. Biol. Inorg. Chem., 5:575 (2000).

U. Bierbach, M. Sabat, and N. Farrell: Inversion of the cis-geometry requirement for cytotoxicity in novel platinum(II) complexes containing the bidentate N,O-donor pyridine-2-yl-acetate (PyAc). Inorg. Chem., 39:1882 (2000).

U. Bierbach, Y. Qu, T. W. Hambley, J. Peroutka, H. L. Nguyen, M. Doedee and N. Farrell: Synthesis, structure, biological activity, and DNA binding of platinum(II) complexes of the type trans-[PtCl2(NH3)L] (L = planar nitrogen base). Effect of L and cis/trans isomerism on sequence specificity and unwinding properties observed in globally platinated DNA. Inorg. Chem. 38:3535 (1999).

N. Farrell, Y. Qu, U. Bierbach, M. Valsecchi and E. Menta: Structure-activity relationships within dinuclear and trinuclear platinum phase I clinical anticancer agents. In 30 Years of Cisplatin - Chemistry and Biochemistry of a Leading Anticancer Drug. B. Lippert, ed.; Verlag HCA, Basel, Switzerland, 1999.

U. Bierbach and N. Farrell: Structural and reactivity studies on the ternary system guanine/methionine/trans-[PtCl2(NH3)L)] (L = NH3, quinoline): Implications for the mechanism of action of nonclassical trans-platinum antitumor complexes. JBIC, 3:570 (1998).

A. Zákovscá, O. Nováková, Z. Balcarová, U. Bierbach, N. Farrell, and V. Brabec: DNA interactions of antitumor trans-[PtCl2(NH3)quinoline]. Eur. J. Biochem., 254:547 (1998).

U. Bierbach, T. W. Hambley and N. Farrell: Modification of Platinum(II) Antitumor Complexes with Sulfur Ligands. 1. Synthesis, Structure and Spectroscopic Properties of Cationic Complexes of the Types [PtCl(diamine)(L)]NO3 and [{PtCl(diamine)}2(L-L)](NO3)2 (L = Monofunctional Thiourea Derivative; L-L = Bifunctional Thiourea Derivative). Inorg. Chem. 37:708 (1998).

U. Bierbach, J. D. Roberts and N. Farrell: Modification of Platinum(II) Antitumor Complexes with Sulfur Ligands. 2. Reactivity and Nucleotide Binding Properties of Cationic Complexes of the Types [PtCl(diamine)(L)]NO3 and [{PtCl(diamine)}2(L-L)](NO3)2 (L = Monofunctional Thiourea Derivative; L-L = Bifunctional Thiourea Derivative) in Relation to Their Cytotoxicity. Inorg. Chem. 37:717 (1998).

U. Bierbach and N. Farrell: Modulation of Nucleotide Binding of Trans-Platinum Complexes by Planar Ligands. A Combined Proton NMR and Molecular Mechanics Study. Inorg. Chem. 36:3657 (1997).

U. Bierbach, T. W. Hambley, J. D. Roberts, and N. Farrell:Oxidative Addition of the Dithiobis(formamidinium) Cation to Platinum(II) Chloro Am(m)ine Compounds: Studies on Structure, Spectroscopic Properties, Reactivity and Cytotoxicity of a New Class of Platinum(IV) Complexes Exhibiting S-Thiourea Coordination. Inorg. Chem. 35:4865 (1996).

U. Bierbach and J. Reedijk:An Unusual Route to Potential Platinum Antitumor Compounds: Synthesis, Reactivity, and Spectroscopic Properties of the Pt(IV) Complex fac-[PtCl3(NH3)2L]Cl. Angew. Chem. Int. Ed. Engl. 33:1632 (1994).

 

Patents

N. Farrell and U. Bierbach: Water soluble transplatinum complexes with antitumor activity and method of using same. U.S. patent 6,001,872, Dec. 1999.

N. Farrell and U. Bierbach: Platinum complexes with anti-viral activity and method of using same. U.S. patent 6,113,934, Sep. 2000.