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.
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