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JHU Chemistry

Selected Peer-Reviewed Publications

“Curtailing the Hydroxylaminobarbituric Acid - Hydantoin Rearrangement to Favor HNO Generation” Guthrie, D. A.; Nourian, S.; Takahashi, C. G.; Toscano, J. P. J. Org. Chem. 2014, submitted.

“The “Catch-and-Release” of HNO with Pyrazolones” Guthrie, D. A.; Ho, A.; Takahashi, C. G.; Collins, A.; Morris, M.; Toscano, J. P. J. Org. Chem. 2014, submitted.

“Comparison of HNO reactivity with tryptophan and cysteine in small peptides” Keceli, G.; Moore, C. D.; Toscano, J. P. Bioorg. Med. Chem. Lett. 2014, 24, 3710-3713.

“Reactivity of C-terminal cysteines with HNO” Keceli, G.; Toscano, J. P. Biochemistry 2014, 53, 3689-3698.

“Post-study caffeine administration enhances memory consolidation in humans” Borota, D.; Murray, E.; Keceli, G.; Chang, A.; Watabe, J. M.; Ly, M.; Toscano, J. P.; Yassa, M. A. Nat. Neurosci. 2014, 17, 201-203.

“NMR detection and study of hydrolysis of HNO-derived sulfinamides” Keceli, G.; Moore, C. D.; Labonte, J. W.; Toscano, J. P. Biochemistry 2013, 52, 7387-7396.

“HNO enhances SERCA2a activity and cardiomyocyte function by promoting redox-dependent phospholamban oligomerization” Sivakumaran, V.; Stanley, B. A.; Tocchetti, C. G.; Ballin, J. D.; Caceres, V.; Zhou, L.; Keceli, G.; Rainer, P. P.; Lee, D. I.; Huke, S.; Ziolo, M. T.; Kranias, E. G.; Toscano, J. P.; Wilson, G. M.; O'Rourke, B.; Kass, D. A.; Mahaney, J. E.; Paolocci, N. Antioxid. Redox Signal. 2013, 19, 1185-1197.

Invited Article for a special issue of Journal of Inorganic Biochemistry on the Bioinorganic Chemistry of HNO: “Oxidation of N-hydroxy-L-arginine by Hypochlorous Acid to Form Nitroxyl (HNO)” Cline, M. R.; Chavez, T.A.; Toscano, J. P. J. Inorg. Biochem. 2013, 118, 148-154.

Invited Article for a special issue of Physical Chemistry Chemical Physics on New Insights Into Organic Chemistry from Forefront Physical Measurements: “Nanosecond Time-Resolved IR Study of Thiobenzoylnitrene” Liu, Y.; Evans, A. S.; Toscano, J. P. Phys. Chem. Chem. Phys. 2012, 14, 10438-10444.

“Reactivity of Nitroxyl-Derived Sulfinamides”  Keceli, G.; Toscano, J. P. Biochemistry 2012, 51, 4206-4216.

“Development of N-Substituted Hydroxylamines as Efficient Nitroxyl (HNO) Donors” Guthrie, D. A.; Kim, N. Y.; Siegler, M. A.; Moore, C. D.; Toscano, J. P. J. Am. Chem. Soc. 2012, 134, 1962-1965.

“Optimization of HNO Production from N,O-bis-Acylated Hydroxylamine Derivatives”  Sutton, A. D.; Williamson, M.; Weismiller, H.; Toscano, J. P. Org. Lett. 2012, 14, 472-475.

“The Chemistry of NO- and HNO-Producing Diazeniumdiolates” Evans, A. S.; Toscano, J. P. in The Chemistry of Hydroxylamines, Oximes, and Hydroxamic Acids, Vol. 2; Rappoport, Z.; Liebman, J. F., Eds.; John Wiley & Sons, 2011, 917-932.

“Detection of Nitroxyl (HNO) by a Prefluorescent Probe”  Cline, M. R.; Toscano, J. P. J. Phys. Org. Chem. 2011, 24, 993-998.

“Detection of Nitroxyl (HNO) by Membrane Inlet Mass Spectrometry” Cline, M. R.; Tu, C.; Silverman, D. N.; Toscano, J. P. Free Rad. Biol. Med., 2011, 50, 1274-1279.

“Weinreb Amides in Carbene Chemistry: A Time-Resolved IR Investigation into a Potential Intramolecular Stabilization Mechanism” Evans, A. S.; Sundaram, G. S. M.; Sabmannshausen, J.; Toscano, J. P.; Tippmann, E. M. Org. Lett., 2010, 12, 4616-4619.

“Photogeneration and Reactivity of Acyl Nitroso Compounds” Evans, A. S.; Cohen, A. D.; Gurard-Levin, Z. A.; Kebede, N.; Celius, T. C.; Miceli, A. P.; Toscano, J. P. Can. J. Chem. 2010, 89, 130-138.

“Phospholamban Thiols Play a Central Role in Activation of the Cardiac Muscle Sarcoplasmic Reticulum Calcium Pump by Nitroxyl” Froehlich, J. P.; Mahaney, J. E.; Keceli, G.; Pavlos, C. M.; Goldstein, R.; Redwood, A. J.; Sumbilla, C.; Lee, D. I.; Tocchetti, C. G.; Kass, D. A.; Paolocci, N.; Toscano, J. P. Biochemistry 2008, 47, 13150-13152.

“2-Hydroxy-5-nitrobenzyl as a Diazeniumdiolate Protecting Group: Application in NO-Releasing Polymers with Enhanced Biocompatibility” Xu, H.; Reynolds, M. M.; Cook, K. E.; Evans, A. S.; Toscano, J. P. Org. Lett. 2008, 10, 4593-4596.

“Photochemistry of N-Acetyl-, N-Trifluoroacetyl-, N-Mesyl-, and N-Tosyldibenzothiophene Sulfilimines” Desikan, V.; Liu, Y.; Toscano, J. P.; Jenks, W. S. J. Org. Chem. 2008, 73, 4398-4414.

“Photochemistry of Sulfilimine-Based Nitrene Precursors: Generation of Both Singlet and Triplet Benzoylnitrene” Desikan, V.; Liu, Y.; Toscano, J. P.; Jenks, W. S. J. Org. Chem. 2007, 72, 6848-6859.

“Time-Resolved Infrared (TRIR) Studies of Organic Reactive Intermediates” Toscano, J. P. in Reviews of Reactive Intermediate Chemistry; Platz, M. S.; Moss, R. A.; Jones, M., Jr., Eds.; John Wiley & Sons, 2007.

“Nitroxyl Improves Cellular Heart function by Directly Enhancing Cardiac Sarcoplasmic Reticulum Ca2+ Cycling” Tocchetti, C. G.; Wang, W.; Froehlich, J. P.; Huke, S.; Aon, M. A.; Wilson, G. M.; Di Benedetto, G.; O’Rourke, B.; Gao, W. D.; Wink, D. A.; Toscano, J. P.; Zaccolo, M.; Bers, D. M.; Valdivia, H. H.; Cheng, H.; Kass, D. A.; Paolocci, N. Circ. Res. 2007, 100, 96-104.

“Generation of Oxynitrenes and Confirmation of Their Triplet Ground States” Wasylenko, W. A.; Kebede, N.; Showalter, B. M.; Matsunaga, N.; Miceli, A. P.; Liu, Y.; Ryzhkov, L. R.; Hadad, C. M.; Toscano, J. P. J. Am. Chem. Soc. 2006, 128, 13142-13150.

“8-Bromo-7-hydroxyquinoline as a Photoremovable Protecting Group for Physiological Use: Mechanism and Scope” Zhu, Y.; Pavlos, C. M.; Toscano, J. P.; Dore, T. M. J. Am. Chem. Soc. 2006, 128, 4267-4276.

“Crystal Lattice Effects on the Orientation and Orbital Degeneracy of Nitric Oxide Trapped in Nitramine Single Crystals” Ryzhkov, L. R.; Toscano, J. P. Cryst. Growth Des. 2005, 5, 2066-2072.

“Donors of HNO” Miranda, K. M.; Nagasawa, H. T.; Toscano, J. P. Current Topics Med. Chem. 2005, 5, 649-664.

“Photosensitive Precursors to Nitric Oxide” Pavlos, C. M.; Xu, H.; Toscano, J. P. Current Topics Med. Chem. 2005, 5, 637-647.

“The Mechanism of Photoinduced Acylation of Amines by N-Acyl-5,7-dinitroindoline as Determined by TRIR Spectrosopy” Cohen, A. D.; Helgen, C.; Bochet, C. G.; Toscano, J. P. Org. Lett. 2005, 7, 2845-2848.

“Caged Nitric Oxide” Pavlos, C. M.; Xu, H.; Toscano, J. P. in Phototriggers, Photoswitches, and Caged Compounds, Dynamic Studies in Biology; Goelder, M; Givens, R. S., Eds.; Wiley-VCH: Weinheim, 2005.

“Photoinduced Carbon Monoxide Migration in a Synthetic Heme-Copper Complex” Fry, H. C.; Cohen, A. D.; Toscano, J. P.; Meyer, G. J.; Karlin, K. D. J. Am. Chem. Soc. 2005, 127, 6225-6230.

“The Triplet State of a Platinum Acetylide Chromophore Examined by Time-Resolved IR Spectroscopy and Density Functional Theory” Cooper, T. M.; Blaudeau, J.-P.; Hall, B. C.; Rogers, J. E.; McLean, D. G.; Liu, Y.; Toscano, J. P. Chem. Phys. Lett. 2004, 400, 239-244.

“Controlled Photochemical Release of Nitric Oxide from Diazeniumdiolates” Pavlos, C. M.; Xu, H.; Toscano, J. P. Free Radical Biol. Med., 2004, 37, 745-752.

“Time-Resolved IR Studies of α-Lactones” Showalter, B. M.; Toscano, J. P. J. Phys. Org. Chem. 2004, 17, 743-748.

“Time-Resolved IR Detection and Study of an Iminooxirane Intermediate” Cohen, A. D.; Showalter, B. M.; Toscano, J. P. Org. Lett. 2004, 6, 401-403.

“Photochemistry of 1-(N,N-Diethylamino)diazen-1-ium-1,2-diolate: An Experimental and Computational Investigation” Pavlos, C. M.; Cohen, A. D.; D'Sa, R. A.; Sunoj, R. B.; Wasylenko, W. A.; Kapur, P.; Relyea, H. A.; Kumar, N. A.; Hadad, C. M.; Toscano, J. P. J. Am. Chem. Soc. 2003, 125, 14934-14940.

“The Photochemistry of Diazirines” Celius, T. C.; Toscano, J. P. In CRC Handbook of Organic Photochemistry and Photobiology, 2nd Edition; Horspool, W.; Lenci, F., Eds.; CRC Press: Boca Raton, FL, 2003, 92-1 – 92-10.

“Photochemical Reactivity of α-Diazocarbonyl Compounds” Celius, T. C.; Wang, Y.; Toscano, J. P. In CRC Handbook of Organic Photochemistry and Photobiology, 2nd Edition; Horspool, W.; Lenci, F., Eds.; CRC Press: Boca Raton, FL, 2003, 90-1 – 90-16.

“Time-Resolved IR Studies of Cyclic Enone Triplet Excited States and their Reactions with Alkenes” Cohen, A. D.; Showalter, B. M.; Brady, D. A.; Kenesky, C. A.; Toscano, J. P. Phys. Chem. Chem. Phys. 2003, 5, 1059-1063.

“Matrix Isolation, Time-Resolved IR, and Computational Study of the Photochemistry of Benzoyl Azide” Pritchina, E. A.; Gritsan, N. P.; Maltsev, A.; Bally, T.; Autrey, T.; Liu, Y.; Wang, Y.; Toscano, J. P. Phys. Chem. Chem. Phys. 2003, 5, 1010-1018.

“Direct Observation of an Acyl Nitroso Species in Solution by Time-Resolved IR Spectroscopy” Cohen, A. D.; Zeng, B.-B.; King, S. B.; Toscano, J. P. J. Am. Chem. Soc. 2003, 125, 1444-1445.

“Energetics of Aqueous Oxyanions of Nonmetals and Metalloids” Toscano, J. P.; Deakyne, C. A.; Liebman, J. F. Struct. Chem. 2003, 14, 315-320.

“Preparation and Reactivity of O2-Sulfonated Diazeniumdiolates” D’Sa, R. A.; Wang, Y.; Ruane, P. H.; Showalter, B. M.; Saavedra, J. E.; Davies, K. M.; Citro, M. L.; Booth, M. N.; Keefer, L. K.; Toscano, J. P. J. Org. Chem. 2003, 68, 656-657.

“The Energetics of Nitric Oxide Generation Upon Protonation of Diazeniumdiolates” Hammad, L. A.; Ruane, P. H.; Kumar, N. A.; Toscano, J. P.; Wenthold, P. G Int. J. Mass. Spec., 2003, 222, 269-279.

“The Fragmentation of Alkoxychlorocarbenes in Hydrocarbon Solvents and in Low-Temperature Argon Matrices” Moss, R. A.; Ma, Y.; Zeng, F.; Sauers, R.; Bally, T.; Maltsev, A.; Toscano, J. P.; Showalter, B. M. J. Phys. Chem. A 2002, 106, 12280-12291.

“Controlled Photochemical Release of Nitric Oxide from O2-Naphthylmethyl- and O2-Naphthylallyl-Substituted Diazeniumdiolates” Bushan, K. M.; Xu, H.; Ruane, P. H.; D’Sa, R. A.; Pavlos, C. M.; Smith, J. A.; Celius, T. C.; Toscano, J. P. J. Am. Chem. Soc., 2002, 124, 12640-12641.

“Controlled Photochemical Release of Nitric Oxide from O2-Benzyl Substituted Diazeniumdiolates” Ruane, P. H.; Bushan, K. M.; Pavlos, C. M.; D’Sa, R. A.; Toscano, J. P. J. Am. Chem. Soc. 2002, 124, 9806-9811.

“Computational and Experimental Studies of the Effect of Substituents on the Singlet-
Triplet Energy Gap in Phenyl(carbomethoxy)carbene” Geise, C. M.; Wang, Y.; Mykhaylova, O.; Frink, B. T.; Toscano, J. P.; Hadad, C. M. J. Org. Chem. 2002, 67, 3079-3088.

“Bridgehead Carbocations via Carbene Fragmentation: Erasing a 1010 Kinetic Preference” Moss, R. A.; Zheng, F.; Fede, J.-M.; Ma, Y.; Sauers, R. R.; Toscano, J. P.; Showalter, B. M. J. Am. Chem. Soc. 2002, 124, 5258-5259.

“Solvent Dependence of the 2-Napthyl(carbomethoxy)carbene Singlet-Triplet Energy Gap” Wang, Y.; Hadad, C. M.; Toscano, J. P. J. Am. Chem. Soc. 2002, 124, 1761-1767.

“Reversible Carbon Monoxide Photodissociation from Cu(I) Coordination Compounds” Scaltrito, D. V.; Fry, H. C.; Showalter, B. M.; Thompson, D. W.; Liang, H.-C.; Zhang, C. X.; Kim, E.; Toscano, J. P.; Karlin, K. D.; Meyer, G. J. Inorg. Chem. 2001, 40, 4514-4515.

“The 2-Norbornyl Cation via the Fragmentation of exo- and endo-2-Norbornyloxychloro-carbenes: Distinction Without Much Difference” Moss, R. A.; Zheng, F.; Sauers, R. R.; Toscano, J. P. J. Am. Chem. Soc. 2001, 123, 8109-8116.

“Identification of a Vibrational Frequency Corresponding to H-Atom Translocation in Hypericin” Showalter, B. M.; Datta, A.; Chowdury, P. K.; Park, J.; Bandyopadhyay, P.; Kesavan, S.; Zeng, Y.; Kraus, G. A.; Gordon, M. S.; Toscano, J. P.; Petrich, J. W. Photochem. Photobiol. 2001, 74, 157-163.

Invited Review: “Structure and Reactivity of Organic Intermediates as Revealed by Time-Resolved IR Spectroscopy” Toscano, J. P. in Advances in Photochemistry, Neckers, D. C; von Bünau, G.; Jenks, W. S., Eds., John Wiley & Sons, New York, 2001, Vol. 26, pp. 41-91.

“Chemistry of the Diazeniumdiolates. 3. Photoreactivity” Srinivasan, A.; Kebede, N.; Saavedra, J. E.; Nikolaitchik, A. V.; Brady, D. A.; Yourd, E.; Davies, K. M.; Keefer, L. K.; Toscano, J. P. J. Am. Chem. Soc. 2001, 123, 5465-5472.

“New Kinetics Methodologies Applied To Carbene Fragmentation Reactions” Moss, R. A.; Johnson, L. A.; Yan, S.; Toscano, J. P.; Showalter, B. M. J. Am. Chem. Soc. 2000, 122, 11256-11257.

“Structures of Reactive Nitrenium Ions: Time-Resolved Infrared Laser Flash Photolysis and Computational Studies of Substituted N-Methyl-N-arylnitrenium Ions” Srivastava, S.; Ruane, P. H.; Toscano, J. P.; Sullivan, M. B.; Cramer, C. J.; Chiapperino, D.; Reed, E. C.; Falvey, D. E. J. Am. Chem. Soc. 2000, 122, 8271-8278.

“Time-Resolved IR Studies of Triplet 1,3-Cyclopentanediyl” Showalter, B. M.; Bentz, T. C.; Ryzhkov, L. R.; Hadad, C. M.; Toscano, J. P. J. Phys. Org. Chem. 2000, 13, 309-312.

“Time-Resolved IR Studies of 4-Diazo-3-Isochromanone: Direct Kinetic Evidence for a Non-Carbene Route to Ketene” Wang, Y.; Toscano, J. P. J. Am. Chem. Soc. 2000, 122, 4512-4513.

“Time-Resolved IR Studies of 2-Naphthyl(carbomethoxy)carbene: Reactivity and Direct Experimental Estimate of the Singlet/Triplet Energy Gap” Wang, Y.; Yuzawa, T.; Hamaguchi, H.; Toscano, J. P. J. Am. Chem. Soc. 1999, 121, 2875-2882.

“Generation and Study of Benzylchlorocarbene from a Phenanthridene Precursor” Nigam, M.; Platz, M. S.; Showalter, B. M.; Toscano, J. P.; Johnson, R. J. Am. Chem. Soc. 1998, 120, 8055-8059.

“Structural Differences between pp* and np* Acetophenone Triplet Excited States as Revealed by Time-Resolved IR Spectroscopy” Srivastava, S.; Yourd, E.; Toscano, J. P. J. Am. Chem. Soc. 1998, 120, 6173-6174.


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