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- Detailed Information
Alexander Greer
Professor
Chemistry
Location: 341 Ingersoll Hall Extension
Phone: 718.951.5000 x2830
Fax: 718.951.4607
Email:
Alexander Greer's Web site
Alexander Greer's group is interested in fundamental aspects of organic chemistry. Factors that control reactions of oxygen and sulfur species are of interest. The group is involved in research of atomic oxygen, singlet molecular oxygen and other reactive and cytotoxic agents. Some molecules used in their studies (polysulfanes) exhibit cytotoxic properties that must have taken eons to evolve, formed by marine invertebrates to deter predators. The synthetic chemistry aims to create polysulfanes with increased anti-tumor activity over those found in nature. Using chemicals synthesized with functionality to initiate cell responses or the modulation of specific cell sensitivity is of interest. Computations are used to try to deepen our understanding of experiments. The group often probes organic mechanisms with ab initio and density functional theory.
Education:
Postdoctoral Fellow, UCLA - 1999 (Organic Chemistry)
Ph.D., University of Wyoming - 1996 (Organic Chemistry)
Areas of Expertise:
Physical organic chemistry; photooxidation mechanisms; singlet oxygen; preparative-, theoretical- and photochemistry; molecular mechanisms of toxicity; enantiospecific toxicity; antitumor and antifungal compounds; natural products; organism chemical defense mechanisms; natural selection of biological agents; and chemical evolution.
Doctoral Rotation Projects:
Techniques to be learned upon doing lab rotations may include: methods in photochemistry, organic synthesis and drug design; nuclear magnetic resonance and liquid chromatography-mass spectrometry (LCMS) techniques, laser spectroscopy and computational theory.
Books and Publications
Bartusik, D., D. Aebisher, A.M. Lyons and A. Greer. "Bacterial Inactivation by a Singlet Oxygen Bubbler: Identifying Factors Controlling the Toxicity of Singlet O2 Bubbles." Environmental Science & Technology 46: 12098-104. (Books and Publications: Peer Reviewed Article) 2012
Bartusik, D., D. Aebisher, B. Ghafari, A.M. Lyons and A. Greer. "Generating Singlet Oxygen Bubbles: A New Mechanism for Gas-Liquid Oxidations in Water." Langmuir 28: 3053-60. (Books and Publications: Peer Reviewed Article) 2012
Bartusik, D., D. Aebisher, G. Ghosh, M. Minnis and A. Greer. "Fluorine End-Capped Optical Fibers for Photosensitizer Release and Singlet Oxygen Production." Journal of Organic Chemistry 77: 4557-65. Featured article. (Books and Publications: Forthcoming Publications) 2012
Castillo, Á., L. Lee and A. Greer. "Encapsulation and Convex-face Thiozonolysis of Triatomic Sulfur (S3) with Carbon Nanotubes." Journal of Physical Organic Chemistry 25: 42-49. (Books and Publications: Peer Reviewed Article) 2012
Kimani, S., G. Ghosh, A. Ghogare, B. Rudshteyn, D. Bartusik, T. Hasan and A. Greer. "Synthesis and Characterization of Mono-, Di-, and Tri-Poly(ethylene glycol) Chlorin e6 Conjugates for the Photokilling of Human Ovarian Cancer Cells." Journal of Organic Chemistry 77: 10638-47. (Books and Publications: Peer Reviewed Article) 2012
Rudshteyn, B., A. Castillo and A. Greer. "Theoretical Study of a Nonpeptidic Polydisulfiude Alpha-Helix." Journal of Sulfur Chemistry. Special issue in honor of Professor Eric Block. In press. (Books and Publications: Forthcoming Publications) 2012
"Chemistry Students and Human Rights." Chemistry and Biodiversity 8: 2158-61. (Books and Publications: Peer Reviewed Article) 2011
J.M. Motto, A. Castillo, A. Greer, L.K. Montemayer, E.E. Sheepwash, A.L. Schwan. "Synthetic Scope, Computational Chemistry and Mechanism of the Base Induced 5-Endo Cyclizations of Benzyl Alkynyl Sulfides." Tetrahedron 67: 1002-10. (Books and Publications: Peer Reviewed Article) 2011
Kruft, B.I. and A. Greer, "Photosensitization Reactions In Vitro and In Vivo." Photochemistry and Photobiology 87: 1204-13. (Books and Publications: Peer Reviewed Article) 2011
Mahendran, A., Y. Kopkalli, G. Ghosh, A. Ghogare, M. Minnis, B.I. Kruft, M. Zamadar, D. Aebisher, L. Davenport and A. Greer. "A Hand-held Fiber-optic Implement for the Site-specific Delivery of Photosensitizer and Singlet Oxygen." Photochemistry and Photobiology 87: 1330-37. (Books and Publications: Peer Reviewed Article) 2011
Slayden, S.W., A. Greer and J.F. Liebman. "Peroxynitrogen: A Study of Nitrogen/Oxygen Heterocycles With N-O and O-O or N-O-O Bonding." The Chemistry of Functional Groups (Patai series). The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids, Volume 2. Eds. Z. Rappoport and J.F. Liebman. Chichester: Wiley. 549-76. (Books and Publications: Chapter) 2011
Zamadar, M., G. Ghosh, A. Mahendran, M. Minnis, B.I. Kruft, A. Ghogare, D. Aebisher and A. Greer. "Photosensitizer Drug Delivery via an Optical Fiber." Journal of the American Chemical Society 133: 7882-91. (Books and Publications: Peer Reviewed Article) 2011
A. Mahendran, A. Voung, D. Aebisher, Y. Gong, R. Bittman, G. Arthur, A. Kawamura and A. Greer. "Synthesis, Characterization, Mechanism of Decomposition, and Antiproliferative Activity of a Class of PEGylated Benzopolysulfanes Structurally Similar to the Natural Product Varacin." Journal of Organic Chemistry 75: 5549-57. (Books and Publications: Peer Reviewed Article) 2010
Aebisher, D., M. Zamadar, A. Mahendran, G. Ghosh, C. McEntee and A. Greer. "Fiber-optic Singlet Oxygen [1O2 (1∆g)] Generator Device Serving as a Point Selective Sterilizer." Photochemistry and Photobiology 86: 890-94. (Books and Publications: Peer Reviewed Article) 2010
Review of Oxidation of Organic Compounds by Dioxiranes, by Waldemar Adam, Cong-Gui Zhao, Chantu R. Saha-Möller and Kavitha Jakka. New York: Wiley (2009). Angewandte Chemie International Edition 49: 251. (Books and Publications: Book Review) 2010
Zamadar, M. and A. Greer. "Singlet Oxygen as a Reagent in Organic Synthesis." Handbook of Synthetic Photochemistry Eds. A. Albini and M. Fagnoni. Weinheim, Germany: Wiley-VCH. 353-86. (Books and Publications: Chapter) 2010
Castillo, A. and A. Greer. "Theoretical Studies of a Singlet Oxygen-Releasing Dioxapaddlane (1,4-Diicosa naphthalene-1,4-endoperoxide)." Structural Chemistry 20: 399-407. (Books and Publications: Peer Reviewed Article) 2009
Raber, M.L., A. Castillo, A. Greer and C.A. Townsend. "A Conserved Lysine in beta-Lactam Synthetase Assists Ring Cyclization: Implications for Clavam and Carbapenem Biosynthesis." ChemBioChem 10: 2904-12. (Books and Publications: Peer Reviewed Article) 2009
Zamadar, M., D. Aebisher and A. Greer. "Singlet Oxygen Delivery Through the Porous Cap of a Hollow-Core Fiber Optic Device." Journal of Physical Chemistry B 113: 15803-06. (Books and Publications: Peer Reviewed Article) 2009
Aebisher, D. and A. Greer. Preface: "Extreme Sulfur Chemistry." Journal of Sulfur Chemistry 29: 241. (Books and Publications: Peer Reviewed Article) 2008
Aebisher, D., N.S. Azar, M. Zamadar, H.D. Gafney, N. Gandra, R. Gao and A. Greer. "Singlet Oxygen Chemistry in Water. A Porous Vycor Glass--Supported Photosensitizer." Journal of Physical Chemistry B 112: 1913-17. (Books and Publications: Peer Reviewed Article) 2008
Castillo, A., J.F. Liebman and A. Greer. "Quinones, Monoradicals and Diradicals From 3- and 4-Mercaptocatechol, and 3,4-Bismercaptocatechol: A Computational Study of a Plausibly Biomimetic Reaction." Journal of Sulfur Chemistry 29: 445-57. (Books and Publications: Peer Reviewed Article) 2008
Giaimuccio, J., M. Zamadar, D. Aebisher, G.J. Meyer and A. Greer. "Singlet Oxygen Chemistry in Water. 2. Photophysics of Quenching of a Photosensitizer by O2 at the Water/Porous Glass Interface." Journal of Physical Chemistry B 112: 15646-50. (Books and Publications: Peer Reviewed Article) 2008
Greer, A. and D. Aebisher, editors. Special Issue: "Extreme Sulfur Chemistry." Journal of Sulfur Chemistry 29: 241-457. (Books and Publications: Peer Reviewed Article) 2008
Greer, A. and J.F. Liebman. "Paradigms and Paradoxes: Energetics of the Oxidative Cleavage of Azo Compounds." Structural Chemistry 19: 817-18. (Books and Publications: Peer Reviewed Article) 2008
Greer, E.M., D. Aebisher, A. Greer and R. Bentley. "Computational Studies of the Tropone Natural Products, Thiotropocin, Tropodithietic Acid, and Troposulfenin. Significance of Thiocarbonyl-enol Tautomerism." Journal of Organic Chemistry 73: 280-83. (Books and Publications: Peer Reviewed Article) 2008
"Organic Chemistry: Molecular Crosstalk." Nature 447: 273-74. (Books and Publications: Peer Reviewed Article) 2007
Aebisher, D., E.M. Brzostowska, M. Adaickapillai and A. Greer. "Regioselective (Biomimetic) Synthesis of a Pentasulfane from Ortho-benzoquinone." Journal of Organic Chemistry 72: 2951-55. (Books and Publications: Peer Reviewed Article) 2007
Aebisher, D., E.M. Brzostowska, N. Sawwan, R. Ovalle and A. Greer. "Implications for the Existence of a Heptasulfur Linkage in Natural o-Benzopolysulfanes." Journal of Natural Products 70: 1492-94. (Books and Publications: Peer Reviewed Article) 2007
Brzostowska, E.M., M. Paulynice, R. Bentley and A. Greer. "Planar Chirality Due to a Polysulfur Ring in Natural Pentathiepin Cytotoxins. Implications of Planar Chirality for Enantiospecific Biosynthesis and Toxicity." Chemical Research in Toxicology 20: 1046-52. (Books and Publications: Peer Reviewed Article) 2007
Frank, A.T., A. Adenike, D. Aebisher, A. Greer, R. Gao and J.F. Liebman. "Paradigms and Paradoxes: Energetics of the Oxidative Cleavage of Indigo." Structural Chemistry 18: 71-74. (Books and Publications: Peer Reviewed Article) 2007
Frank, A.T., N.S. Farina, N. Sawwan, O.R. Wauchope, M. Qi, E.M. Brzostowska, W. Chan, F.W. Grasso, P. Haberfield and A. Greer. "Natural Macromolecules Have a Possible Limited Structural Diversity." Molecular Diversity 11: 115-18. (Books and Publications: Peer Reviewed Article) 2007
Sawwan, N. and A. Greer. "Rather Exotic Types of Cyclic Peroxides: Heteroatom Dioxiranes." Chemical Reviews 107: 3247-85. (Books and Publications: Peer Reviewed Article) 2007
Wauchope, O.R., S. Shakya, N. Sawwan, J.F. Liebman and A. Greer. "Photocleavage of Plasmid DNA by Dibenzothiophene S-oxide Under Anaerobic Conditions." Journal of Sulfur Chemistry 28: 11-16. (Books and Publications: Peer Reviewed Article) 2007
"Christopher Foote's Discovery of the Role of Singlet Oxygen [1O2 (1∆g)] in Photosensitized Oxidation Reactions." Accounts of Chemical Research 39: 797-804. (Books and Publications: Peer Reviewed Article) 2006
"Preface: Organic Chemistry of Singlet Oxygen." Tetrahedron 62: 10603. (Books and Publications: Peer Reviewed Article) 2006
Gandra, N., Aaron T. Frank, O. Le Gendre, N. Sawwan, D. Aebisher, J.F. Liebman, K.N. Houk, A. Greer and R. Gao. "Possible Singlet Oxygen Generation from the Photolysis of Indigo Dyes in Methanol, DMSO, Water, and Ionic Liquid, 1-Butyl-3-methylimidazolium tetrafluoroborate." Tetrahedron 62: 10771-76. (Books and Publications: Peer Reviewed Article) 2006
Greer, A., O.R. Wauchope, N.S. Farina, P. Haberfield and J.F. Liebman. "Paradigms and Paradoxes: Mechanisms for Possible Enhanced Biological Activity of Bilaterally Symmetrical Chemicals." Structural Chemistry 17: 347-50. (Books and Publications: Peer Reviewed Article) 2006
Sawwan, N. and A. Greer. "The Generation of Mono- and Bis-dioxiranes from 2,3-Butanedione." Journal of Organic Chemistry 71: 5796-99. (Books and Publications: Peer Reviewed Article) 2006
Symposium-In-Print: "Organic Chemistry of Singlet Oxygen." Tetrahedron 62: 10603-776. (Books and Publications: Edited Book) 2006
Clennan, E.L., S.E. Hightower and A. Greer. "Conformationally Induced Electrostatic Stabilization of Persulfoxides. A New Suggestion for Inhibition of Physical Quenching of Singlet Oxygen by Remote Functional Groups." Journal of the American Chemical Society 127: 11819-27. (Books and Publications: Peer Reviewed Article) 2005
Sawwan, N., E.M. Brzostowska and A. Greer. "Substituent Effects on the Reactivity of Benzo-1,2-Dithiolan-3-one 1-Oxides and Its Possible Application to the Synthesis of DNA-Targeting Drugs." Journal of Oragnic Chemistry 70: 6968-71. (Books and Publications: Peer Reviewed Article) 2005
Brzostowska, E.M. and A. Greer. "Polysulfane Antitumor Agents from o-Benzyne. An Odd-Even Alternation Found in the Stability of Products, o-C6H4Sx (x = 1 to 8)." Journal of Organic Chemistry 69: 5483-85. (Books and Publications: Peer Reviewed Article) 2004
Voloshchuk, T., N.S. Farina, O.R. Wauchope, M. Kiprowska, P. Haberfield and A. Greer. "Molecular Bilateral Symmetry of Natural Products. Prediction of Selectivity of Dimeric Molecules by Density Functional Theory and Semiempirical Calculations." Journal of Natural Products 67: 1141-46. (Books and Publications: Peer Reviewed Article) 2004
"Perspective: A View of Unusual Peroxides." Science 302: 235-36. (Books and Publications: Peer Reviewed Article) 2003
Brzostowska, E.M. and A. Greer. "The Role of Amine in the Mechanism of Pentathiepin (Polysulfur) Antitumor Agents." Journal of the American Chemical Society 125: 396-404. (Books and Publications: Peer Reviewed Article) 2003
Singleton, D.A., M.J. Szymanski, M.P. Meyer, A.G. Leach, K.T. Kuwata, J.S. Chen, A. Greer, C.S. Foote and K.N. Houk. "Mechanism of Ene Reactions of Singlet Oxygen. A Two-Step No-Intermediate Mechanism." Journal of the American Chemical Society 125: 1319-28. (Books and Publications: Peer Reviewed Article) 2003
Thomas, K.B. and A. Greer. "Gauging the Significance of Atomic Oxygen [O(3P)] in Sulfoxide Photochemistry. A Method for Hydrocarbon Oxidation." Journal of Organic Chemistry 68: 1886-91. (Books and Publications: Peer Reviewed Article) 2003
"On the Origin of Cytotoxicity of the Natural Product Varacin. A Novel Example of a Pentathiepin Reaction that Provides Evidence for a Triatomic Sulfur Intermediate." Journal of the American Chemical Society 123: 10379-86. (Books and Publications: Peer Reviewed Article) 2001
Lucien, E. and A. Greer. "Electrophilic Oxidant Produced in the Photodeoxygenation of 1,2-Benzodiphenylene Sulfoxide." Journal of Organic Chemistry 66: 4576-79. (Books and Publications: Peer Reviewed Article) 2001
Greer, A., G. Vassilikogiannakis, K.-C. Lee, T.S. Koffas, K. Nahm and C.S. Foote. "Reaction of Singlet Oxygen with trans-4-Propenylanisole. Formation of [2 + 2] Products with Added Acid." Journal of Organic Chemistry 65: 6876-78. (Books and Publications: Peer Reviewed Article) 2000
Reznik, R. and A. Greer. "An Adjacent Thioester Provides Apical-Directed Stabilization to 3-Isothiazolidinone 1-Oxide Heterocycles." Chemical Research in Toxicology 13: 1193-98. (Books and Publications: Peer Reviewed Article) 2000
Wu, S. and A. Greer. "Attractive Through-Space S-O Interaction in the DNA-Cleaving Antitumor Antibiotic Leinamycin." Journal of Oragnic Chemistry 65: 4883-87. (Books and Publications: Peer Reviewed Article) 2000
Greer, A., K.A. Conklin, K. Faull, K.N. Houk and C.S. Foote. "Low Temperature FAB Mass and NMR Spectroscopic Identification of an Unstable Episulfoxide." Journal of Oragnic Chemistry 64: 1432-33. (Books and Publications: Peer Reviewed Article) 1999
Clennan, E.L., M.-F. Chen, A. Greer and F. Jensen. "Experimental and Computational Evidence for the Formations of Iminopersulfinic Acids." Journal of Organic Chemistry 63: 3397-3402. (Books and Publications: Peer Reviewed Article) 1998
Jensen, F. A. Greer and E.L. Clennan. "Reaction of Organic Sulfides with Singlet Oxygen. A Revised Mechanism." Journal of the American Chemical Society 120: 4439-49. (Books and Publications: Peer Reviewed Article) 1998
Greer, A., M.-F. Chen, F. Jensen and E.L. Clennan. "Experimental and ab Initio Computational Evidence for New Peroxidic Intermediates (Iminopersulfinic Acids). Substituent Effects in the Photooxidations of Sulfenic Acid Derivatives." Journal of the American Chemical Society 119: 4380-87. (Books and Publications: Peer Reviewed Article) 1997
Clennan, E.L. and A. Greer. "Steric and Electronic Effects on the Partitioning of a Persulfinyl Intermediate Along the Physical Quenching and Chemical Reaction Channels." Tetrahedron Letters 37: 6093-96. (Books and Publications: Peer Reviewed Article) 1996
Clennan, E.L. and A. Greer. "The Effect of Alcohols on the Photooxidative Behavior of Diethylsulfide." Journal of Organic Chemistry 61: 4793-97. (Books and Publications: Peer Reviewed Article) 1996
Greer, A., F. Jensen and E.L. Clennan. "Ring Strain Effects on the Interconversion of Intermediates in the Reaction of Organic Sulfides with Singlet Oxygen." Journal of Organic Chemistry 61: 4107-10. (Books and Publications: Peer Reviewed Article) 1996
Clennan, E.L., P. Dobrowolski and A. Greer. "Reaction of Singlet Oxygen with Thietane. A Novel Example of a Self-Catalyzed Reaction which Provides Evidence for a Thiadioxirane Intermediate." Journal of the American Chemical Society 117: 9800-03. (Books and Publications: Peer Reviewed Article) 1995
Awards, Honors and Fellowships
National Institute of General Medical Sciences of the National Institutes of Health, SC1 grant, for "Site-specific Delivery of Photosensitizer and Singlet Oxygen in vivo." $1,522,120; September 2010-May 2014. (Grants and Fellowships) 2010
National Institutes of Health, SCORE grant, for "Biosynthetic Formation of Polysulfane Anticancer Agents." $693,520; March 2006-February 2010. (Grants and Fellowships) 2006
Sara Jane Rhoads Award for Outstanding Research for the Ph.D. Degree, University of Wyoming and American Chemical Society. (Awards and Honors) 1996
Conferences, Seminars and Symposiums
"Photosensitized Generation of Singlet Oxygen--Towards a Photochemical Surgical Knife or Singlet Oxygen Scapel." Rutgers University. Newark, N.J., April 26. (Conferences, Seminars and Symposiums: Invited Talk) 2012
"Towards a Photochemical Surgical Knife or Singlet Oxygen Scapel." NYU Poly. Brooklyn, N.Y., March 9. (Conferences, Seminars and Symposiums: Invited Talk) 2012
Bartusik, Dorota, David Aebisher, BiBi Ghafari, Alan Lyons and Alexander Greer. "Generating Singlet Oxygen Bubbles: Aiming for PDT and Wound Disinfection Application." (Conferences, Seminars and Symposiums: Invited Talk) 2012
"Towards a Photochemical Surgical Knife or Singlet Oxygen Scapel." University at Albany, SUNY Albany. Nov. 1. (Conferences, Seminars and Symposiums: Invited Talk) 2011
"Encouraging Undergraduate Student Involvement in Defending the Human Rights of Scientists." American Chemical Society National Meeting & Exposition. Anaheim, Calif., March 31. (Conferences, Seminars and Symposiums: Contributed Talk) 2011
"Fiber Optic-Guided Photosensitizer Drug Delivery." American Chemical Society National Meeting & Exposition. Anaheim, Calif., March 28. (Conferences, Seminars and Symposiums: Conference Presentation) 2011
"Photosensitizer Drug Delivery via an Optical Fiber." 14th Congress of the European Society for Photobiology. Geneva, Sept. 1-6. (Conferences, Seminars and Symposiums: Contributed Talk) 2011
"The Integration of Organic Chemistry and Activism in Human Rights." Westchester Chemical Society. Dec. 7. (Conferences, Seminars and Symposiums: Invited Talk) 2011
"Fiber Optic Device for Targeted Singlet Oxygen Delivery for Potential Application in Human Diseases such as Brain Tumors" American Chemical Society National Meeting. Boston, Aug. 22-26. (Conferences, Seminars and Symposiums: Conference Presentation) 2010
"Mechanism of Photodynamic Therapy and Its Use in the Treatment of Cancer." Stern College of Yeshiva University. April. (Conferences, Seminars and Symposiums: Invited Talk) 2010
"Point Selective Delivery of Singlet Oxygen via a Fiber Optic Device: Toxic Action of Light, Dyes, and Oxygen." 35th Scientific Meeting of the American Society for Photobiology. Providence, R.I., June 13. (Conferences, Seminars and Symposiums: Contributed Talk) 2010
"Singlet Oxygen Delivery via a Fiber Optic-Bound Photosensitizer." American Chemical Society National Meeting. Boston, Aug. 22-26. (Conferences, Seminars and Symposiums: Contributed Talk) 2010
"Delivery of Singlet Molecular Oxygen in vivo via Optical Fibers." Gordon Research Conference on Physical Organic Chemistry. Holderness, N.H., July 2. (Conferences, Seminars and Symposiums: Invited Talk) 2009
Professional Leadership
Co-chair, "Photoinduced Phenomena in Chemistry and Physics." American Society for Photobiology 2012: 36th Meeting. Montreal. (Professional Leadership: Organizational Leadership Position) 2012
Associate editor, Photochemistry and Photobiology. Wiley-Blackwell. (Professional Leadership: Public Service) 2009
Board of Editors, Structural Chemistry. Springer Publishers. (Professional Leadership: Public Service) 2006
Deputy executive officer, Department of Chemistry, CUNY Graduate Center. (Professional Leadership: Committee Service) 2004
Community Activities
Co-chair, Committee of Concerned Scientists (http://concernedscientists.org/). 2011





