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Photo of Stephen G. DiMagno

Stephen G. DiMagno

Professor, Medicinal Chemistry and Pharmacognosy

Contact Information

833 S. Wood Street (781)
589 PHARM
Chicago, Illinois 60612

Phone: (312) 413-1964

Education

  • PhD, Chemistry, University of California, Berkeley, 1991
  • BA, Chemistry, Swarthmore College, 1985

Research Lab Summary

Clinicians rely heavily on positron emission tomography (PET) imaging in the diagnosis, staging and management of cancer, cardiac, and neurological diseases. PET procedures are able to pinpoint specific biochemical activity in the body, and thus may identify disease in its earliest stages. Subsequent treatment can be easily managed by noninvasive assessment of response to therapy via PET imaging. The patient typically receives an injected radioactive drug that travels through the body and acts as a beacon, identifying tumors or the uptake of chemicals in specific tissues (dopamine to the brain, for example). The most widely used "radiotag" is an isotope of fluorine (18F) used with an analogue of glucose, 18F -FDG ([18F]-2-fluoro-2-deoxyglucose), and constitutes 94% of currently used clinical PET imaging agents. 18F-Fluorine has an attractively short half-life (109.8 minutes), which allows a patient to be quickly discharged from the hospital with no concern for residual patient radioactivity. However, the short half-life poses challenges in imaging agent preparation, as they must be made rapidly and efficiently each day near the point of use. The DiMagno lab has developed fluorination chemistry which permits a wide range of radiotracers to be made economically on automated commercial radiosynthesis equipment with sufficient yield, activity, and purity to meet diverse clinical needs. We have developed methodology that allows for making stable, crystalline diaryliodonium salts and for using them for the efficient radiofluorination of most chemical ring structures. We have already developed precursors (destined to be tagged with radioactive isotopes) for cancer, cardiac, and brain PET imaging. Key insights from our group’s work are: 1) low-polarity solvents suppress hitherto unknown side reactions, which severely limited the yields of fluorinated compounds obtained from diaryliodonium fluorides; 2) diaryliodonium salts undergo facile aryl exchange reactions, and 3) metal-free syntheses are key to increasing the stability of diaryliodonium salts. These insights allowed us to improve the yield of 18F-labeled compounds obtained from diaryliodonium salts dramatically. We have established collaborations with St. Jude Children's Research Hospital, UCSF, and other universities to implement our radiochemical labeling strategies more widely. Our laboratory welcomes collaborations with academic radiopharmacies. Current research in the DiMagno group focuses on preparation and use of diaryliodonium salts in the creation of new radiotracers for PET imaging applications, improving synthesis of existing PET radiotracers, and development of novel therapeutic agents based upon PET radiotracers. We are focused on creating compounds for diagnostic scanning of cancer, depression, bio-distribution of environmental contaminants and others. Additionally, we utilize diaryliodonium salts as potent electrophilic arylating agents. Students in the DiMagno group will receive training in organic synthesis, physical organic chemistry, instrumentation and spectroscopy.

Research Interests

Radiopharmaceutical chemistry, medical imaging, organofluorine chemistry, kinetics, and computational chemistry.

Teaching Interests

Organic and medicinal chemistry, physical organic chemistry

Professional Organizations

  • Chair, Division of Fluorine Chemistry, American Chemical Society
  • Vice Chair, Membership, Division of Fluorine Chemistry, American Chemical Society
  • Executive Committee Member, Division of Fluorine Chemistry, American Chemical Society

Patents and Intellectual Property

  • Fluorination of Aromatic Rings System
  • Processes and reagents for maing diaryliodonium salts
  • Fluorination of Aromatic Rings System
  • Iodonium Cyclophanes for SECURE arene functionalization
  • Detection and quantification of anions
  • Anhydrous fluoride salts and methods for their production
  • Methods and agents for preparing 18F-radiolabeled fluorinating agents
  • Heavily fluorinated sugar analogs
  • Electron-Deficient Porphyrins and Processes and Intermediates for Preparing Same
  • Method for Preparation of Electron Deficient Porphyrins
  • Pyrrolic Compounds
  • Hyperpolarizable compounds and optoelectronic devices fabricated therefrom
  • Metal-Mediated Cross-Coupling with Ring-Metalated Porphyrins
  • Metal-Mediated Cross-Coupling with Ring-Metalated Porphyrins
  • Electron-Deficient Porphyrins and Processes and Intermediates for Preparing Same
  • Metal-Mediated Cross-Coupling with Ring-Metalated Porphyrins
  • Substituted Porphyrins, Porphyrin-Containing Polymers, and Synthetic Methods Therefor

Intellectual Contributions

Journal Article

  • 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. , DiMagno S, Elsinga PH. "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, II CR. "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.
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