Photo of Professor Stephen G. DiMagno

Stephen G. DiMagno


Professor, Pharmaceutical Sciences

Contact

Building & Room:

589 PHARM

Address:

833 S. Wood Street, Chicago, Illinois, 60612

Office Phone:

(312) 413-1964

About

Research Interests: Radiopharmaceutical chemistry, medical imaging, organofluorine chemistry, kinetics, and computational chemistry.
Teaching Interests: Organic and medicinal chemistry, physical organic chemistry

Selected Publications

  • Kelly JM, Amor-Coarasa A, Ponnala S, Nikolopoulou A, Williams C, Jr NA, Thiele D, Schlyer JJ, Wilson S, DiMagno JW, Babich . A Single Dose of 225Ac-RPS-074 Induces a Complete Tumor Response in a LNCaP Xenograft Model.. Journal of nuclear medicine : official publication, Society of Nuclear Medicine. 2018;. doi:10.2967/jnumed.118.219592.
  • Vāvere AL, Neumann KD, Butch ER, Hu B, DiMagno S, Snyder SE. Improved, one-pot synthesis of 6-[18 F]fluorodopamine and quality control testing for use in patients with neuroblastoma.. Journal of labelled compounds & radiopharmaceuticals. 2018;. doi:10.1002/jlcr.3685.
  • Kelly JM, Amor-Coarasa A, Nikolopoulou A, Wüstemann T, Barelli P, Kim D, Williams C, Zheng X, Bi C, Hu B, Warren JD, Hage DS, DiMagno S, Babich JW. “Dual-target binding ligands with modulated pharmacokinetics for endoradiotherapy of prostate cancer”. Journal of Nuclear Medicine. 2017;58(9):1442-1449. doi:10.2967/jnumed.116.188722.
  • Linstad EJ, Vāvere AL, Hu B, Kempinger JJ, Snyder SE, DiMagno S. Thermolysis and radiofluorination of diaryliodonium salts derived from anilines.. Organic & biomolecular chemistry. 2017;15(10):2246-2252. doi:10.1039/c7ob00253j.
  • Kothari P, De BP, He B, Chen A, Chiuchiolo MJ, Kim D, Nikolopoulou A, Amor-Coarasa A, Dyke JP, Voss HU, Kaminsky SM, Foley CP, Vallabhajosula S, Hu B, DiMagno S, Sondhi D, Crystal RG, Babich JW, Ballon D. Radioiodinated Capsids Facilitate In Vivo Non-Invasive Tracking of Adeno-Associated Gene Transfer Vectors.. Scientific reports. 2017;7:39594. doi:10.1038/srep39594.
  • Neumann KD, Qin L, Vavere AL, Shen B, Miao Z, Chin FT, Shulkin BL, Snyder SE, DiMagno S. Efficient automated syntheses of high specific activity 6-[18F]fluorodopamine using a diaryliodonium salt precursor. J. Labelled Compd. Radiopharm.. 2016;59(1):30-34. doi:10.1002/jlcr.3367.
  • Qin L, Hu B, Neumann KD, Linstad EJ, McCauley K, Veness J, Kempinger JJ, DiMagno S. A Mild and General One-Pot Synthesis of Densely Functionalized Diaryliodonium Salts. Eur. J. Org. Chem.. 2015;2015(27):5919-5924. doi:10.1002/ejoc.201500986.
  • Hu B, Vavere AL, Neumann KD, Shulkin BL, DiMagno S, Snyder SE. A Practical, Automated Synthesis of meta-[18F]Fluorobenzylguanidine for Clinical Use. ACS Chem. Neurosci.. 2015;6(11):1870-1879. doi:10.1021/acschemneuro.5b00202.
  • Hu B, Miller WH, Neumann KD, Linstad EJ, DiMagno S. An Alternative to the Sandmeyer Approach to Aryl Iodides. Chem. – Eur. J.. 2015;21(17):6394-6398. doi:10.1002/chem.201500151.
  • Kuik W, Kema IP, Brouwers AH, Zijlma R, Neumann KD, Dierckx , Rudi A. J. O. S, DiMagno PH, Elsinga . In vivo biodistribution of no-carrier-added 18FDOPA, produced by a new nucleophilic substitution approach, compared with carrier-added 18FDOPA, prepared by conventional electrophilic substitution. J. Nucl. Med.. 2015;56(1):106-112. doi:10.2967/jnumed.114.145730.
  • Jiang H, DiMagno S, DeGrado TR. Production and transport of gaseous 18F-synthons: 18F-acyl fluorides. J. Fluorine Chem.. 2015;180:181-185. doi:10.1016/j.jfluchem.2015.09.012.
  • Hu B, DiMagno S. Reactivities of vinyl azides and their recent applications in nitrogen heterocycle synthesis. Org. Biomol. Chem.. 2015;13(13):3844-3855. doi:10.1039/C5OB00099H.
  • Jin Z, Xu B, DiMagno S, Hammond GB. Replacement of BF4- by PF6- makes Selectfluor greener. J. Fluorine Chem.. 2012;143:226-230. doi:10.1016/j.jfluchem.2012.05.010.
  • Biffinger JC, Uppaluri S, Sun H, DiMagno S. Ligand Fluorination to Optimize Preferential Oxidation of Carbon Monoxide by Water-Soluble Rhodium Porphyrins. ACS Catal.. 2011;1(7):764-771. doi:10.1021/cs2001187.
  • Graskemper JW, Wang B, Qin L, Neumann KD, DiMagno S. Unprecedented Directing Group Ability of Cyclophanes in Arene Fluorinations with Diaryliodonium Salts. Org. Lett.. 2011;13(12):3158-3161. doi:10.1021/ol201080c.
  • Wang B, Cerny RL, Uppaluri S, Kempinger JJ, DiMagno S. Fluoride-promoted ligand exchange in diaryliodonium salts. J. Fluorine Chem.. 2010;131(11):1113-1121. doi:10.1016/j.jfluchem.2010.04.004.
  • Wang B, Qin L, Neumann KD, Uppaluri S, Cerny RL, DiMagno S. Improved Arene Fluorination Methodology for I(III) Salts. Org. Lett.. 2010;12(15):3352-3355. doi:10.1021/ol101154h.
  • Wang B, Graskemper JW, Qin L, DiMagno S. Regiospecific Reductive Elimination from Diaryliodonium Salts. Angew. Chem., Int. Ed.. 2010;49(24):4079-4083, S4079/1-S4079/35. doi:10.1002/anie.201000695.
  • Sun H, Koch AS, DiMagno S. Rapid preparation of fluorinated aromatic heterocycles. ACS Symp. Ser.. 2009;1003(Fluorinated Heterocycles):85-104. doi:10.1021/bk-2009-1003.ch005.
  • Sun H, Wang B, DiMagno S. A method for detecting water in organic solvents. Org. Lett.. 2008;10(20):4413-4416. doi:10.1021/ol8015429.
  • Sun H, DiMagno S. Competitive demethylation and substitution in N,N,N-trimethylanilinium fluorides. J. Fluorine Chem.. 2007;128(7):806-812. doi:10.1016/j.jfluchem.2007.03.009.
  • Sun H, DiMagno S. Fluoride relay: a new concept for the rapid preparation of anhydrous nucleophilic fluoride salts from KF. Chem. Commun. (Cambridge, U. K.). 2007;(5):528-529. doi:10.1039/B614368G.
  • Sun H, DiMagno S. Room-temperature nucleophilic aromatic fluorination: experimental and theoretical studies. Angew. Chem., Int. Ed.. 2006;45(17):2720-2725. doi:10.1002/anie.200504555.
  • Atkins JM, Moteki SA, DiMagno S, Takacs JM. Single Enantiomer, Chiral Donor-Acceptor Metal Complexes from Bisoxazoline Pseudoracemates. Org. Lett.. 2006;8(13):2759-2762. doi:10.1021/ol060836s.
  • DiMagno S, Sun H. The strength of weak interactions: aromatic fluorine in drug design. Curr. Top. Med. Chem. (Sharjah, United Arab Emirates). 2006;6(14):1473-1482. doi:10.2174/156802606777951127.
  • Sun H, DiMagno S. Anhydrous Tetrabutylammonium Fluoride. J. Am. Chem. Soc.. 2005;127(7):2050-2051. doi:10.1021/ja0440497.
  • Sun H, Biffinger JC, DiMagno S. Ion pairing in tetraphenylporphyrin oxidation: a semiquantitative study. Dalton Trans.. 2005;(19):3148-3154. doi:10.1039/b506109a.
  • Biffinger JC, Kim HW, DiMagno S. The polar hydrophobicity of fluorinated compounds. ChemBioChem. 2004;5(5):622-627. doi:10.1002/cbic.200300910.
  • Biffinger JC, Sun H, Nelson AP, DiMagno S. Differential substituent effects of β-halogens in water-soluble porphyrins. Org. Biomol. Chem.. 2003;1(4):733-736. doi:10.1039/b209345f.
  • Sun H, Xue F, Nelson AP, Redepenning J, DiMagno S. Reversible Electrochemical Generation of a Rhodium(II) Porphyrin: Thwarting Disproportionation with Weakly Coordinating Anions. Inorg. Chem.. 2003;42(15):4507-4509. doi:10.1021/ic0345830.
  • Sun H, Smirnov VV, DiMagno S. Slow electron transfer rates for fluorinated cobalt porphyrins: electronic and conformational factors modulating metalloporphyrin ET. Inorg. Chem.. 2003;42(19):6032-6040. doi:10.1021/ic034705o.
  • Lin VS, Iovine PM, DiMagno S, Therien MJ, Malinak S, Coucouvanis D. Synthesis of selected supramolecules. Dipyrryl and porphyrinic precursors to supramolecular conjugated (porphinato)metal arrays: synthesis of dipyrrylmethane and zinc(II). Inorg. Synth.. 2002;33:55-61.
  • DiMagno S, Sun H, Redepenning JG, Xue F. Electrochemistry and in situ spectroelectrochemistry of a perfluorinated rhodium porphyrin in coordinating and noncoordinating media. Abstracts of Papers, 221st ACS National Meeting, San Diego, CA, United States, April 1-5, 2001. 2001;:INOR-109.
  • Wertsching AK, Koch AS, DiMagno S. On the Negligible Impact of Ruffling on the Electronic Spectra of Porphine, Tetramethylporphyrin, and Perfluoroalkylporphyrins. J. Am. Chem. Soc.. 2001;123(17):3932-3939. doi:10.1021/ja003137y.
  • DiMagno S. Porphyrin ring ruffling and bathochromic absorption spectra: Resemblance, contiguity, or causation?. Abstracts of Papers, 221st ACS National Meeting, San Diego, CA, United States, April 1-5, 2001. 2001;:INOR-729.
  • DiMagno S, Nelson AP. Selectivity of H-D exchange activity catalyzed by Rh(F28TPP). Abstracts of Papers, 221st ACS National Meeting, San Diego, CA, United States, April 1-5, 2001. 2001;:INOR-241.
  • Smirnov VV, Woller EK, Tatman D, DiMagno S. Structure and Photophysics of β-Octafluoro-meso-tetraarylporphyrins. Inorg. Chem.. 2001;40(11):2614-2619. doi:10.1021/ic001116z.
  • Audebert P, Miomandre F, Di Magno SG, Smirnov VV, Hapiot P. Polymerization of 3,4-Difluoropyrrole: Electrochemical and Physicochemical Behavior of Poly(Difluoropyrrole). Chem. Mater.. 2000;12(7):2025-2030. doi:10.1021/cm000222w.
  • Nelson AP, DiMagno S. Umpolung of a Metal-Carbon Bond: A Potential Route to Porphyrin-Based Methane Functionalization Catalysts. J. Am. Chem. Soc.. 2000;122(35):8569-8570. doi:10.1021/ja001380r.
  • Smirnov VV, Woller EK, DiMagno S. 19F NMR and Structural Evidence for Spin-State Modulation of Six-Coordinate Cobalt(II) in a Weak Field Porphyrin Ligand. Inorg. Chem.. 1998;37(19):4971-4978. doi:10.1021/IC980156O.
  • Woller EK, Smirnov VV, DiMagno S. A Straightforward Synthesis of 3,4-Difluoropyrrole. J. Org. Chem.. 1998;63(16):5706-5707. doi:10.1021/JO9805798.
  • Kim HW, Rossi P, Shoemaker RK, DiMagno S. Structure and Transport Properties of a Novel, Heavily Fluorinated Carbohydrate Analog. J. Am. Chem. Soc.. 1998;120(35):9082-9083. doi:10.1021/JA9803714.
  • Woller EK, DiMagno S. 2,3,7,8,12,13,17,18-Octafluoro-5,10,15,20-tetraarylporphyrins and Their Zinc Complexes: First Spectroscopic, Electrochemical, and Structural Characterization of a Perfluorinated Tetraarylmetalloporphyrin. J. Org. Chem.. 1997;62(6):1588-1593. doi:10.1021/JO962159T.
  • DiMagno S. Mesomolecules: From Molecules to Materials Search Series, Volume 1. Edited by G. David Mendenhall, Arthur Greenberg, and Joel F. Liebman. J. Am. Chem. Soc.. 1997;119(21):5079-5080. doi:10.1021/JA9552555.
  • LeCours SM, DiMagno S, Therien MJ. Exceptional Electronic Modulation of Porphyrins through meso-Arylethynyl Groups. Electronic Spectroscopy, Electronic Structure, and Electrochemistry of [5,15-Bis[(aryl)ethynyl]-10,20-diphenylporphinato]zinc(II) Complexes. X-ray Crystal Structures of [5,15-Bis[(4’-fluorophenyl)ethynyl]-10,20-diphenylporphinato]zinc(II) and 5,15-Bis[(4’-methoxyphenyl)ethynyl]-10,20-diphenylporphyrin. J. Am. Chem. Soc.. 1996;118(47):11854-11864. doi:10.1021/JA962403Y.
  • DiMagno S, Dussault PH, Schultz JA. Fluorous Biphasic Singlet Oxygenation with a Perfluoroalkylated Photosensitizer. J. Am. Chem. Soc.. 1996;118(22):5312-5313. doi:10.1021/JA960736P.
  • LeCours SM, Guan H, DiMagno S, Wang CH, Therien MJ. Push-Pull Arylethynyl Porphyrins: New Chromophores That Exhibit Large Molecular First-Order Hyperpolarizabilities. J. Am. Chem. Soc.. 1996;118(6):1504-10. doi:10.1021/JA953610L.
  • DiMagno S, Wertsching AK, Ross CR, II . Electronic Consequences of Nonplanar Core Conformations in Electron-Deficient Porphyrins: The Structure and Spectroscopic Properties of [5,10,15,20-Tetrakis(heptafluoropropyl)porphinato]cobalt(II). J. Am. Chem. Soc.. 1995;117(31):8279-80. doi:10.1021/ja00136a030.
  • DiMagno S, Williams RA, Therien MJ. Facile synthesis of meso-tetrakis(perfluoroalkyl)porphyrins: spectroscopic properties and x-ray crystal structure of highly dlectron-deficient 5,10,15,20-tetrakis(heptafluoropropyl)porphyrin. J. Org. Chem.. 1994;59(23):6943-8. doi:10.1021/jo00102a017.
  • Lin VS, DiMagno S, Therien MJ. Highly conjugated, acetylenyl bridged porphyrins: new models for light-harvesting antenna systems. Science (Washington, D. C.). 1994;264(5162):1105-11. doi:10.1126/science.8178169.
  • DiMagno S, Lin VS, Therien MJ. Catalytic conversion of simple haloporphyrins into alkyl-, aryl-, pyridyl-, and vinyl-substituted porphyrins. J. Am. Chem. Soc.. 1993;115(6):2513-15. doi:10.1021/ja00059a060.
  • DiMagno S, Lin VS, Therien MJ. Facile elaboration of porphyrins via metal-mediated cross-coupling. J. Org. Chem.. 1993;58(22):5983-93. doi:10.1021/jo00074a027.
  • Carter PW, DiMagno S, Porter JD, Streitwieser A. π-Stacking and aggregation of pyridinium-substituted indolizines. J. Phys. Chem.. 1993;97(5):1085-96. doi:10.1021/j100107a017.
  • Feng AS, Speer DV, DiMagno S, Konings MS, Streitwieser A. The structure and reactivity of 1,2,3,3,-tetrakis[4-(dimethylamino)pyridinium-1-yl]cyclopropene salts. J. Org. Chem.. 1992;57(10):2902-9. doi:10.1021/jo00036a027.
  • DiMagno S, Waterman KC, Speer DV, Streitwieser A. The structure and remarkable stability of a per-pyridinium substituted allyl radical. J. Am. Chem. Soc.. 1991;113(12):4679-81. doi:10.1021/ja00012a046.
  • Moore R, DiMagno S, Yoon HW. EPR spectroscopy of manganous-ion doped calcium oxide. An advanced physical chemistry laboratory experiment. J. Chem. Educ.. 1986;63(9):818-20.
  • Education

  • PhD, Chemistry, University of California, Berkeley
  • BA, Chemistry, Swarthmore College
  • Professional Memberships

  • Division of Fluorine Chemistry, American Chemical Society
  • Division of Fluorine Chemistry, American Chemical Society
  • Division of Fluorine Chemistry, American Chemical Society