Thomas C. Bruice Group

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Papers:Topic:Nucleotide Analogs and Phosphate Esters

   

Nucleotide Analogs and Phosphate Esters – Materials

373. A. Salehi; H-Y. Mei; and T.C. Bruice. Synthesis and DNA-Binding Studiesof New Cationic Guanidine and Betaineamide Tetraphenylpophyrins. Tet. Lett. 1991, 32, 3453.

385. T.C. Bruice; H.-Y. Mei; G.-X. He; and V. Lopez. Rational Design of Substituted Tri-Pyrrole Peptides Which Complex with DNA by Both Selective Minor Groove Binding and Electrostatic Interaction with Phosphate Backbone. Proc. Natl. Acad. Sci. (USA) 1992, 89, 1700.

393. K.A. Browne and T.C. Bruice. Chemistry of Phosphodiesters, DNA and Models. II. The Hydrolysis of Bis(8-hydroxyquinoline) Phosphate in the Absence and Presence of Metal Ions. J. Am. Chem. Soc. 1992, 114, 4951.

403. G-X. He; K.A. Browne; J.C. Groppe; A. Blasko; H-Y. Mei; and T.C. Bruice. Microgonotropens and Their Interactions with DNA. I. Synthesis of the Tri-Pyrrole Peptides Dien-Microgonotropen-a, -b, and -c and Characterization of Their Interactions with dsDNA. J. Am. Chem. Soc. 1993, 115, 7061.

404. K.A. Browne; G-X. He; and T.C. Bruice. Microgonotropens and Their Interactions with DNA. II. Quantitative Evaluation of Equilibrium Constants for 1:1 and 2:1 Binding of Dien-Microgonotropen-a, -b, and -c as well as Distamycin and Hoechst 33258 to d(GGCGCAAATTTGGCGG)/d(CCGCCAAATTTGCGCC). J. Am. Chem. Soc. 1993, 115, 7072.

405. A. Blasko; K.A. Browne; G-X. He; and T.C. Bruice. Microgonotropens and Their Interactions with DNA. III. Structural Analysis of the 1:1 Complex of d(CGCAAATTTGCG)2 and Dien- Microgonotropen-c by 2D NMR Spectroscopy and Restrained Molecular Modeling. J. Am. Chem. Soc. 1993, 115, 7080.

407. Ö Almarsson; T.C. Bruice; J. Kerr and R. Zuckermann. Molecular Mechanics Calculations of the Structures of Polyamide Nucleic Acid DNA Duplexes and Triple Helical Hybrids. Proc. Natl. Acad. Sci. (USA) 1993, 90, 7518.

409. Ö Almarsson and T.C. Bruice. Peptide Nucleic Acid (PNA) Conformation and Polymorphism in PNA-DNA and PNA-RNA Hybrids. Proc. Natl. Acad. Sci. (USA) 1993, 90, 9542.

410. A. Blaskó and T.C. Bruice. Stoichiometry and Structure of Complexes of DNA Oligomers with Microgonotropens and Distamycin by 1H NMR Spectroscopy and Molecular Modeling. Proc. Natl. Acad. Sci. (USA) 1993, 90, 10018.

414. H.G. Hansma, R.L. Sinsheimer, J. Groppe, T.C. Bruice, V. Elings, G. Gurley, M. Bezanilla, I.A. Mastrangelo, P.V.C. Hough, and P.K. Hansma. Recent Advances in Atomic Force Microscopy of DNA. Scanning 1993, 15, 296.

417. G-X. He, K.A. Browne, A. Blaskó, and T.C. Bruice. Microgonotropens and Their Interactions with DNA. IV. Synthesis of the Tripyrrole Peptides Tren-Microgonotropen-a and -b and Characterization of Their Interactions with DsDNA. J. Am. Chem. Soc. 1994, 116, 3716.

418. A. Blaskó; K.A. Browne; and T.C. Bruice. Microgonotropens and Their Interactions with DNA. V. Structural Characterization of the 1:1 complex of d(CGCAAATTTGCG)2 and Tren-Microgonotropen-b by 2D NMR Spectroscopy and Restrained Molecular Modeling. J. Am. Chem. Soc. 1994, 116, 3726.

419. R.O. Dempcy and T.C. Bruice. The Negative Charge of Alkyl Phosphate Diesters and the Slow-gaited Hydrolysis of RNA and DNA. Catalysis of RNA Hydrolysis through Metal Ion Ligation to the Ester >PO2- Moiety. J. Am. Chem. Soc. 1994, 116, 4511.

421. R. O. Dempcy; Ö. Almarsson; and T. C. Bruice. The Design and Synthesis of DNG: A Polycation Analogue of DNA. Proc. Natl. Acad. Sci. (USA) 1994, 91, 7864.

422. H. G. Hansma; K. A. Browne; M. Bezanilla; and T. C. Bruice. Bending and Straightening of DNA Induced by the Same Ligand: Characterization with the Atomic Force Microscope. Biochemistry 1994, 33, 8436.

424. A. Tsubouchi; T. C. Bruice. A Remarkable (~1013) Rate Enhancement in Phosphonate Ester Hydrolysis Catalyzed by Two Metal Ions. J. Am. Chem. Soc. 1994, 116, 11614.

425. T. Xue; K. A. Browne; T. C. Bruice. A Novel Minor Groove Binding Reagent Designed to Serve as a "Truck" to Carry DNA Modifying Moieties into the Major Groove. Bioconjugate Chem. 1995, 6, 82.

426. T. C. Bruice; A. Blaskó´; R. D. Arasasingham; J-S. Kim; M. Petyak. Hydrolysis of a Phosphate Diester by Simultaneous Carboxylate and Carboxyl Group Participation in a Rigid System with Kinetically Unfavorable Rotamers Frozen Out. J. Am. Chem. Soc. 1995, 117, 3639.

429. R. O. Dempcy; K. A. Browne and T. C. Bruice. Synthesis of the Polycation Thymidyl DNG, It's Fidelity in Binding Polyanionic DNA/RNA, and the Stability and Nature of the Hybrid Complexes. J. Am. Chem. Soc. 1995, 117, 6140.

430. R. O. Dempcy; K. A. Browne; T. C. Bruice. Synthesis of a Thymidyl Pentamer of DNG and Binding Studies with DNA Homopolyoligonucleotides. Proc. Natl. Acad. Sci (USA) 1995, 92, 6097.

431. K. A. Browne; R. O. Dempcy; T. C. Bruice. Binding Studies of Cationic DNG to RNA Homopolynucleotides. Proc. Natl. Acad. Sci(USA) 1995, 92, 7051.

432. A. Blasko; K. A. Browne; T. C. Bruice. NMR Structure of d(CGCA3T3GCG)2:Tren-Microgonotropen-b:Zn(II) Complex and Solution Studies of Metal Ion Complexes of Tren- Microgonotropen-b Interacting with DNA. Bioorganic and Medicinal Chemistry 1995, 3, 631.

434. A. Tsubouchi; T. C. Bruice. Phosphonate Ester Hydrolysis Catalyzed by Two Lanthanum Ions. Intramolecular Nucleophilic Attack of Coordinated Hydroxide and Lewis Acid Activation. J. Am. Chem. Soc. 1995, 117, 7399.

435. Thomas C. Bruice; Andrei Blaskó; and Mark E. Petyak. Participation of two Carboxyl Groups in Phosphodiester Hydrolysis. I. The Hydrolysis of Bis-(2-carboxyphenyl) Phosphate. J. Am. Chem. Soc. 1995, 117, 12064.

436. Thomas C. Bruice; Andrei Blaskó; Ramesh D. Arasasingham; and Jang- Seob Kim. Participation of two Carboxyl Groups in Phosphodiester Hydrolysis. II A Kinetic, Isotopic and 31P NMR Study of the Hydrolysis of a Phosphodiester with Carboxyl Groups Fixed in an Attack Conformation. J. Am. Chem. Soc. 1995, 117, 12070.

437. R. A. Torres and T. C. Bruice. Interresidue Hydrogen Bonding in a PNA.RNA Heteroduplex. Proc. Natl. Acad. Sci (USA) 1996, 93, 649.

440. Dempcy, Robert O.; Bruice, Thomas C.. The synthesis and DNA/RNA hybridization properties of DNG, a putative antisense agent with an attractive polycationic guanidinium backbone. NATO ASI Series, Series C: Mathematical and Physical Sciences 1996, 479(DNA and RNA Cleavers and Chemotherapy of Cancer and Viral Diseases), 143-162.

441. D. Sengupta; A. Blasko; T. C. Bruice. A Microgonotropin Pentaaza Pentabutylamine and its Interactions with DNA. Bioorganic and Med. Chem. 1996, 4, 803.

442. R.O. Dempcy; Jia Luo and T.C. Bruice. Design and Synthesis of Ribonucleic Guanidine: A polycationic analog of RNA. Proc. Natl. Acad. Sci (USA) 1996, 93, 4326.

443. R. A. Torres; Ö. Almarsson and T. C. Bruice. Molecular Mechanics Calculations of the Riboacetal Internucleotide Linkage in Double and Triple Helices. Proc. Natl. Acad. Sci (USA) 1996, 93, 6875.

446. A. Blasko; R. O. Dempcy; E. E. Minyat & T. C. Bruice. Association of Short Strand DNA Oligomers with Guanidinium Linked Nucleosides (DNG). A Kinetic and Thermodynamic Study. J. Am. Chem. Soc. 1996, 118, 7892.

447. T. C. Bruice; A. Tsubouchi; R. O. Dempcy and L. P. Olson. Oneand Two Metal Ion Catalysis of the Hydrolysis of Adenosine-3'-(alkyl)phosphate esters. Models for One and Two Metal Ion Catalysis of RNA Hydrolysis. J. Am. Chem. Soc. 1996, 118, 9867.

448. T. C. Bruice; D. Sengupta; A. Blasko; S-Y. Chiang; & T. A. Beerman. A Microgonotropen Branched Decaaza Decabutylamine and its Interactions with DNA & DNA/Transcription Facor Interactions. Bioorganic and Med. Chem. 1997, 5, 685.

449. S.-Y. Chiang; T. C. Bruice; J. C. Azizkhan; L. Gawron & T. Beerman. Targeting E2F1/DNA Complexes with Microgonotropen DNA Binding Agents. Proc. Natl. Acad. Sci. (USA) 1997, 94, 2811.

452. A. Blasko; E. E. Minyat; R. O. Dempcy & T. C. Bruice. Fidelity of Binding of the Guanidinium Nucleic Acid (DNG) d(Tg)4-T-azido with Short Strand DNA Oligamers {A5G3A5, GA4G3A4G, G2A3G3A3G2,G2A2G5A2G2} with a Guanidinium Linked (DNG) Nucleoside. A Kinetic and Thermodynamic Study. Biochemistry 1997, 36, 7821.

456. T. C. Bruice; Y-C. Yip; A. Blasko; M. E. Petyak; K. A. Browne & F. C. Lightstone. Design, Synthesis, Characterizaton of a Novel Hexa-azacyclophane and Interactions with d(CGCA3T3GCG), ctDNA and T4DNA. Tetrahedron 1997, 53, 8105.

468. D. P. Arya & T. C. Bruice. Replacement of the Negative Phosphodiester Linkages of DNA by Positive S-Methyl Thiourea Linkers: A Novel Approach to Putative Antisense Agents. J. Am. Chem. Soc. 1998, 120, 6619.

465. B. Linkletter & T. C. Bruice. Solid Phase Synthesis of Oligomeric Deoxynucleic Guanidine (DNG): A Polycationic Analogue of DNA. Bioorganic & Med. Lett. 1998, 8, 1285.

466. D. A. Barawkar; B. Linkletter & T. C. Bruice. Synthesis of Protected Guanidinium Linked Dinucleoside for Incorporable into an Oligonucleotide Using Solid Phase DNA Methodology. Bioorganic & Med. Lett. 1998, 8, 1517.

471. D. A. Barawkar & T. C. Bruice. Synthesis, biological properties and nuclease resistance properties of mixed backbone oligodeoxynucleotides containing cationic internucleoside guanidinium linkages: DNG/DNA chimeras. Proc. Natl. Acad. Sci. (USA) 1998, 95, 11047.

476. D. P. Arya & T. C. Bruice. Positively Charged DeoxyNucleic MethylThioureas (DNmt): Synthesis and Binding Properties of Pentameric Thynidyl S-Methyl thiourea. J. Am. Chem. Soc. 1998, 120, 12419.

460. J. Luo & T. C. Bruice. Nanosecond Molecular Dynamics of Hybrid Triplex and Duplex of Polycation Deoxyribonucleic Guanidine (DNG) Strands with a Complimentary DNA Strand. J. Am. Chem. Soc.1998, 120, 1115.

479. Linkletter, B. A.; Szabo, I. E.; Bruice, T. C.. Solid-phase synthesis of deoxynucleic guanidine (DNG) oligomers and melting point and circular dichroism analysis of binding fidelity of octameric thymidyl oligomers with DNA oligomers. J. Am. Chem. Soc. 1999, 121, 3888–3896. PDF

480. Arya, D. P.; Bruice, T. C.. Triple-helix formation of DNA oligomers with methylthiourea-linked nucleosides (DNmt): A kinetic and thermodynamic analysis. Proc. Natl. Acad. Sci. (USA) 1999, 96, 4384–4389.

481. Blaskó, A.; Bruice, T. C.. Recent studies of nucleophilic, general-acid, and metal ion catalysis of phosphate diester hydrolysis. Acc. Chem. Res. 1999, 32, 475–484.

486. Barawkar, D. A.; Bruice, T. C.. Deoxynucleic guanidines/PNA (DNG/PNA) chimeras: oligonucleoside analogues containing cationic guanidinium and neutral amide linkages. J. Am. Chem. Soc.1999, 121, 10418–10419.

487. Arya, D. P.; Bruice, T. C.. Fidelity of deoxynucleic S–methylthiourea (DNmt) binding to DNA oligomers: influence of C mismatches. J. Am. Chem. Soc.1999, 121, 10680–10684.

489. Satz, A. L.; Bruice, T. C.. Synthesis of fluorescent microgonotropen (FMGT–1) and its interactions with the dodecamer d(CCGGAATTCCGG). Bioorg. Med. Chem. Lett. 1999, 9, 3261–3266. PDF

491. Kojima, N.; Bruice, T. C.. Replacement of the phosphorodiester linkages of RNA with guanidinium linkages: The solid-phase synthesis of ribonucleic guanidine. Org. Lett. 2000, 2, 81–84.

496. Arya, D. P.; Bruice, T. C.. Solid-phase synthesis of oligomeric deoxynucleic-thiourea (DNT) and deoxynucleic S–methylthiourea (DNmt): a neutral/polycationic analogue of DNA. Bioorg. Med. Chem. Lett. 2000, 10, 691-693.

498. Linkletter, B. A.; Bruice, T. C.. Solid-phase synthesis of positively charged deoxynucleic guanidine (DNG) modified oligonucleotides containing neutral urea linkages: effect of charge deletions on binding and fidelity. Bioorg. Med. Chem. 2000, 8, 1893-1901.

499. Barakar, D. A.; Kwok; Y.; Bruice, T. W. and Bruice, T. C.. Deoxynucleic Guanidine/Peptide Nucleic Acid Chimeras: Synthesis, Binding and Invasion Studies with DNA. J. Am. Chem Soc. 2000, 122, 5244. PDF

502. Satz, A. L. & Bruice, T. C.. Synthesis of Fluorescent Microgonotropens (FMGTs) and Their Interactions with dsDNA. Bioorg. Med. Chem. 2000, 8, 1871-1880. PDF

507. Satz, A.. L. & Bruice, T. C.. Recognition of nine base pairs in the minor groove of dsDNA by a Tripyrrole Peptide-Hoechst Conjugate. J. Am. Chem. Soc. 2001, 123, 2469-2477. PDF

508. Linkletter, B.; Szabo, I. E. and Bruice, T. C.. Solid phase synthesis of oligopurine deoxynucleic guanidine (DNG) and analysis of binding with DNA oligomers. Nucleic Acid Res. 2001, 29, 2370-2376.

509. Satz, L. S.; White, C. M.; Beerman, T. A. & Bruice, T. C.. Double -stranded DNA binding characteristics and subcellular distribution of a minor groove binding diphenylether bisbenzimidazole. Biochemistry 2001, 40, 6465-6467.

511. White, C. M.; Satz, A. L.; Bruice, T. C. & Beerman, T. A.. Inhibition of transcription factor-DNA complexes and gene expression by a novel microgonotropen. Proc. Natl. Acad. (USA) 2001, 98, 10590-10595.

512. Challa, H. & Bruice, T. C.. Incorporation of positively charged deoxynucleic S-methylthiourea linkages into oligonucleotides: Synthesis and characterization of DNmt/DNA chimera. Bioorg. Med. Chem. Lett. 2001, 11, 2423-2427. PDF

515. White, C. M.; Satz, A. L.; Gawron, L. S.; Bruice, T. C. & Beerman, T. A.. Inhibiting transcription factor/DNA complexes using fluorescent microgonotropens. Biochemica et Biophysica Acta gene expression. 2001, 1574, 100-108.

516. Satz, L. S. & Bruice, T. C.. Recognition of nine base pair sequence in the minor groove of DNA at subpicomolar concemntrations by a novel microgonotropen. Bioorg. & Med. Chem. 2002, 10, 241-262.

517. Kojima, N.; Szabo, I. E. & Bruice, T. C.. Synthesis of ribonucleic guanidine: Replacement of the negative phosphodiester linkages of RNA with positive guanidinium linkages. Tetrahedron 2002, 58, 867-879. PDF

518. Satz, L. S. & Bruice, T. C.. Recognition in the Minor Groove of double-stranded DNA by microgonotropens. Acc. Chem. Res. 2002, 35, 86-95. PDF

532. Reddy, P. M. & Bruice, T. C.. Solid phase synthesis of positively charged deoxynucleic guanidine (DNG) oligonucleotide mixed sequences. Bioorg. & Med. Chem. Lett. 2003, 1281-1285.

536. Reddy, P. M., Jindra, P., Satz, L. S. & Bruice, T. C.. Sequence selective recognition in the minor groove of dsDNA by pyrrole, imidazole-Hochst conjugates. J. Am. Chem. Soc., 2003, 125, 7843-7848.

544. Challa, H. & Bruice, T. C., Deoxynucleic Guanidine: Synthesis and incorporation of purine nucleosides into positively charged DNG oligonucleotides. Bioorganic & Med. Chem. Lett., 2004, 12, 1475-1481.

548. Reddy, P.M. and Bruice, T.C., Solid-Phase Synthesis of Positively Charged Deoxynucleic Guanidine (DNG) Tethering a Hoechst 33258 Analogue: Triplex and Duplex Stabilization by Simultaneous Minor Groove Binding. J. Am. Chem. Soc. 2004, 126, 3736-3747. PDF, Supporting Information

550. Szabo, I. & Bruice, T. C., DNG Cytidine: Synthesis and binding properties of octomeric guanidinium-linked deoxycytidine oligomer. Bioorganic & Med. Chem., 2004, 12, 4233-4244.

551. Reddy, M. P., Dexter, R. & Bruice, T.C., DNA sequence recognition in the minor groove by hairpin pyrrole polyamide-Hochst 33258 analog conjugate. Bioorganic & Med. Chem. Lett., 2004, 14, 3803-3807.