| Our group is interested in fundamental aspects of organic chemistry and photochemistry. Factors that control reactions of oxygen and sulfur species are of interest. We are involved in research of singlet molecular oxygen, thiozone, and other reactive and cytotoxic agents. We embrace multiple technologies, even engineering; one project involves fiber optic-based devices for the targeted delivery of cytotoxic singlet oxygen (Figure) for application in diseases, such as brain tumors where high precision is needed in the treatment. Other molecules used in our studies (polysulfanes) exhibit cytotoxic properties that must have taken eons to evolve, formed by marine invertebrates to deter predators. Our synthetic chemistry aims to create polysulfanes with increased anti-tumor activity over those found in nature. Computations are used to try to deepen our understanding of experiments, reaction mechanisms are probed with ab initio and density functional theory. Our research is currently supported by the National Institute of General Medical Sciences of the NIH.
Figure. Fiber optic photoexcitation of a sensitizer on a porous surface followed by emergence of singlet oxygen through the tip (A), and photosensitizer release device (B).
Techniques to be learned upon doing lab rotations may include: Methods in Photochemistry and Photosensitization, Organic Synthesis, and Drug Design; Nanotechnology; NMR and LCMS Techniques, Laser Spectroscopy and Biomedical Engineering, Cell Culturing, Sustainable Engineering and Green Chemistry, and Computational Methods.
CURRENT GROUP 2014
Ashwini Ghogare, Goutam Ghosh, Mihaela Minnis, and Walalawela Niluksha (Ph.D. students); William Fang and Belaid Malek (Master's students); Lucy Kalinin, Beth Manes, and Nwe Win (Undergraduate students); Inna Abramova (Research Assistant).
PUBLICATIONS 2007 - present
[(a) Ph.D. student; (b) MS student; (c) Undergraduate student; (d) Research assistant at Brooklyn College]
- B. Rudshteyn(c); Á. Castillo(a); A. Ghogare(a); J. F. Liebman; A. Greer “Theoretical Study of the Reaction Formalhydrazone with Singlet Oxygen. Fragmentation of the C=N Bond, Ene Reaction, and Other Processes” Photochem. Photobiol. 2013, in press (dedicated to the memory of Prof. Nicholas J. Turro).
- D. Aebisher; D. Bartusik; Y. Liu; Y. Zhao; M. Barahman; Q. Xu; A. M. Lyons; A. Greer "Superhydrophobic Photosensitizers. Mechanistic Studies of 1O2 Generation in the Plastron and Solid/Liquid Droplet Interface" J. Am. Chem. Soc. 2013, 135, 18990–18998.
- I. Abramova(d); A. Greer "Ethnochemistry and Human Rights" Chem. Biodiversity 2013, 10, 1724-1728.
- D. Bartusik; M. Minnis(a); G. Ghosh(a); A. Greer "Autocatalytic-Assisted Photorelease of a Sensitizer Drug Bound to a Silica Support" J. Org. Chem. 2013, 78, 8537–8544.
- M. S. Miranda; J. C. G. Esteves da Silva; A. Castillo(a); A. T. Frank(c); A. Greer; J. A. Brown; B. C. Davis; J. F. Liebman "Amino, Ammonio and Aminioethenes: A Theoretical Study of Their Structure and Energetics" J. Phys. Org. Chem. 2013, 26, 613–625.
- D. Bartusik; D. Aebisher; A. Ghogare(a); G. Ghosh(a); I. Abramova(d); T. Hasan; A. Greer "A Fiberoptic (Photodynamic Therapy Type) Device with a Photosensitizer and Singlet Oxygen Delivery Probe Tip for Ovarian Cancer Cell Killing" Photochem. Photobiol. 2013, 89, 936-941.
- B. Rudshteyn(c); A. Castillo(a); A. Greer "Theoretical Study of a Nonpeptidic Polydisulfide Alpha-Helix" J. Sulfur Chem. 2013, 34, 3-6 (Special Issue in Honor of Prof. Eric Block).
- S. Kimani; G. Ghosh(a); A. Ghogare(a); B. Rudshteyn(c); D. Bartusik; T. Hasan; A. Greer "Synthesis and Characterization of Mono-, Di-, and Tri-Poly(ethylene glycol) Chlorin e6 Conjugates for the Photokilling of Human Ovarian Cancer Cells" J. Org. Chem. 2012, 77, 10638-10647.
- D. Bartusik; D. Aebisher; A. M. Lyons; A. Greer "Bacterial Inactivation by a Singlet Oxygen Bubbler: Identifying Factors Controlling the Toxicity of 1O2 Bubbles" Environ. Sci. Technol. 2012, 46, 12098-12104.
- D. Bartusik; D. Aebisher; G. Ghosh(a); M. Minnis(a); A. Greer "Fluorine End-Capped Optical Fibers for Photosensitizer Release and Singlet Oxygen Production" J. Org. Chem. 2012, 77, 4557-4565 (Featured Article).
- D. Bartusik; D. Aebisher; B. Ghafari; A. M. Lyons; A. Greer “Generating Singlet Oxygen Bubbles: A New Mechanism for Gas-Liquid Oxidations in Water” Langmuir 2012, 28, 3053-3060.
- Á. Castillo(a); L. Lee(b); A. Greer "Encapsulation and Convex-face Thiozonolysis of Triatomic Sulfur (S3) with Carbon Nanotubes" J. Phys. Org. Chem. 2012, 25, 42-49.
- A. Greer "Chemistry Students and Human Rights" Chem. Biodiversity 2011, 8, 2158-2161.
- B. I. Kruft(a); A. Greer "Photosensitization Reactions In Vitro and In Vivo" Photochem. Photobiol. 2011, 87, 1204-1213.
- A. Mahendran(a); Y. Kopkalli; G. Ghosh(a); A. Ghogare(a); M. Minnis(a); B. I. Kruft(a); M. Zamadar(a); D. Aebisher; L. Davenport; A. Greer "A Hand-held Fiber-optic Implement for the Site-specific Delivery of Photosensitizer and Singlet Oxygen" Photochem. Photobiol. 2011, 87, 1330-1337.
- M. Zamadar(a); G. Ghosh(a); A. Mahendran(a); M. Minnis(a); B. I. Kruft(a); A. Ghogare(a); D. Aebisher; A. Greer "Photosensitizer Drug Delivery via an Optical Fiber" J. Am. Chem. Soc. 2011, 133, 7882-7891.
- S. W. Slayden; A. Greer; J. F. Liebman "Peroxynitrogen: A Study of Nitrogen/Oxygen Heterocycles with N-O and O-O or N-O-O Bonding" In: The Chemistry of Functional Groups (Patai series). The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids; Z. Rappoport; J. F. Liebman; Eds.; Vol 2, Wiley: Chichester (2011), pp 549-576.
- J. M. Motto; A. Castillo;(a) 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 2011, 67, 1002-1010.
- D. Aebisher; M. Zamadar(a); A. Mahendran(a); G. Ghosh(a); C. McEntee; A. Greer "Fiber-optic Singlet Oxygen [1O2 (1∆g)] Generator Device Serving as a Point Selective Sterilizer" Photochem. Photobiol. 2010, 86, 890-894.
- M. Zamadar(a); A. Greer "Singlet Oxygen as a Reagent in Organic Synthesis" In Handbook of Synthetic Photochemistry; Albini; A.; Fagnoni; M.; Eds.; Wiley-VCH: Weinheim (2010), pp. 353-386.
- A. Mahendran(a); A. Vuong(c); D. Aebisher; Y. Gong; R. Bittman; G. Arthur; A. Kawamura; A. Greer "Synthesis, Characterization, Mechanism of Decomposition, and Antiproliferative Activity of a Class of PEGylated Benzopolysulfanes Structurally Similar to the Natural Product Varacin" J. Org. Chem. 2010, 75, 5549-5557.
- M. Zamadar(a); D. Aebisher; A. Greer "Singlet Oxygen Delivery Though the Porous Cap of a Hollow-Core Fiber Optic Device" J. Phys. Chem. B 2009, 113, 15803-15806.
- A. Castillo(a); A. Greer "Theoretical Studies of a Singlet Oxygen-Releasing Dioxapaddlane (1,4-Diicosa naphthalene-1,4-endoperoxide)" Struct. Chem. 2009, 30, 399-407.
- M. L. Raber; A. Castillo(a); A. Greer; C. A. Townsend "A Conserved Lysine in beta-Lactam Synthetase Assists Ring Cyclization: Implications for Clavam and Carbapenem Biosynthesis" ChemBioChem 2009, 10, 2904-2912.
- E. M. Greer; D. Aebisher; A. Greer; R. Bentley "Computational Studies of the Tropone Natural Products, Thiotropocin, Tropodithietic acid, and Troposulfenin. Significance of Thiocarbonyl-enol Tautomerism" J. Org. Chem. 2008, 73, 280-283.
- A. Greer; J. F. Liebman "Paradigms and Paradoxes: Energetics of the Oxidative Cleavage of Azo Compounds" Struct. Chem. 2008, 19, 817-818.
- J. Giaimuccio; M. Zamadar(a); D. Aebisher; G. J. Meyer; A. Greer "Singlet Oxygen Chemistry in Water. 2. Photophysics of Quenching of a Photosensitizer by O2 at the Water/Porous Glass Interface." J. Phys. Chem. B 2008, 112, 15646–15650.
- A. Castillo(a); J. F. Liebman; A. Greer "Quinones, Monoradicals and Diradicals From 3- and 4-Mercaptocatechol, and 3,4-Bismercaptocatechol: A Computational Study of a Plausibly Biomimetic Reaction" J. Sulfur Chem. 2008, 29, 445-457.
- D. Aebisher; A. Greer; Editors. Special Issue: "Extreme Sulfur Chemistry" [In: J. Sulfur Chem. 2008; 29, 241-457].
- D. Aebisher; A. Greer; preface. "Extreme Sulfur Chemistry" [In: J. Sulfur Chem. 2008; 29, 241-241].
- D. Aebisher; N. S. Azar(b); M. Zamadar(a); H. D. Gafney; N. Gandra; R. Gao; A. Greer "Singlet Oxygen Chemistry in Water. A Porous Vycor Glass-Supported Photosensitizer" J. Phys. Chem. B 2008, 112, 1913-1917.
- D. Aebisher; E. M. Brzostowska(a); N. Sawwan(a); R. Ovalle; A. Greer "Implications for the Existence of a Heptasulfur Linkage in Natural o-Benzopolysulfanes" J. Nat. Prod. 2007, 70, 1492-1494.
- A. Greer "Organic Chemistry: Molecular Crosstalk" Nature 2007, 447, 273-274.
- E. M. Brzostowska(a); M. Paulynice(c); R. Bentley, A. Greer "Planar Chirality Due to a Polysulfur Ring in Natural Pentathiepin Cytotoxins. Implications of Planar Chirality for Enantiospecific Biosynthesis and Toxicity" Chem. Res. Toxicol. 2007, 20, 1046-1052.
- D. Aebisher; E. M. Brzostowska(a); A. Mahendran(a); A. Greer "Regioselective (Biomimetic) Synthesis of a Pentasulfane From Ortho-benzoquinone" J. Org. Chem. 2007, 72, 2951-2955.
- A. T. Frank(c); N. S. Farina(b); N. Sawwan(a); O. R. Wauchope(c); M. Qi(b); E. M. Brzostowska(a); W. Chan(c); F. W. Grasso; P. Haberfield; A. Greer "Natural Macromolecules Have a Possible Limited Structural Diversity" Molecular Diversity 2007, 11, 115-118.
- N. Sawwan(a); A. Greer "Rather Exotic Types of Cyclic Peroxides: Heteroatom Dioxiranes" Chemical Reviews 2007, 107, 3247-3285.
- A. T. Frank(c); A. Adenike(c); D. Aebisher; A. Greer; R. Gao; J. F. Liebman "Paradigms and Paradoxes: Energetics of the Oxidative Cleavage of Indigo" Struct. Chem. 2007, 18, 71-74.
- O. R. Wauchope(c); S. Shakya(b); N. Sawwan(a); J. F. Liebman; A. Greer "Photocleavage of Plasmid DNA by Dibenzothiophene S-oxide Under Anaerobic Conditions" J. Sulfur Chem. 2007, 28, 11-17.