research in the biros lab

 
 

The Biros group uses organic synthesis to create molecules with unique molecular recognition properties. Currently, we are targeting the chelation of heavy metals and f-elements. We attach chelating groups to multidentate scaffolds, taking advantage of the chelate effect to produce new molecules which have the potential to have a strong affinity for metal cations.

 

Physical Organic Chemistry and Molecular Recognition

Our research group focuses on the organic synthesis of compounds with interesting molecular recognition properties.

Students in this group gain expertise in NMR spectroscopy, metal-ligand coordination chemistry and air-free synthesis techniques.

We also present our work frequently at internal and external conferences.

Possible applications of this research include (but are not limited to) toxic metal chelation therapy (i.e. Arsenic or lead poisoning), nuclear waste remediation, or imaging contrast agents. Our group has also recently delved into the area of tuning lanthanide luminescence with compounds containing the CMPO group. Shown here are

solutions of (from left to right) our free ligand,

and complexes with Eu(III), Sm (III), Tb(III) and

Dy(III) in acetonitrile, irradiated with a

handheld UV lamp.

 

Publications (undergraduate co-authors*)


Katherine M. Coburn,* David A. Hardy,* Michael G. Patterson,* Shelby N. McGraw,* Michael T. Peruzzi,* Felix Boucher,* Bethany Beelen,* Hope T. Sartain,* Thomas Neils, Christopher L. Lawrence, Richard J. Staples, Eric J. Werner, Shannon M. Biros. “f-Element coordination and extraction selectivity using a multipodal carbamoylmethylphosphine oxide ligand on a tridentate phosphoryl scaffoldInorg. Chim. Acta 2016, 449, 96-106; doi: 10.106/j.ica.2016.05.003.


Paul T. Morse,* Richard J. Staples, Shannon M. Biros. “Th(IV) complexes with cis-ethylenebis(diphenylphosphine oxide): X-ray structures and NMR solution studiesPolyhedron – Special Issue on Undergraduate Research, 2016, 114, 2-12; doi: 10.1016/j.poly.2015.05.016.


Sean Riley,* Richard J. Staples, Shannon M. Biros, Felix N. Ngassa. “Crystal structure of phenyl 2,4,5-trichlorobenzenesulfonateActa Cryst. 2016, E72, 789-792; doi:10.1107/S2056989016007325.


Evan P. Beaumier,* Brennan S. Billow, Amrendra K. Singh, Shannon M. Biros, Aaron L. Odom. “A Complex with Nitrogen Single, Double and Triple Bonds to the Same Chromium Atom: Synthesis, Structure and ReactivityChem. Sci. 2016, 7, 2532-2536; doi: 10.1039/C5SC04608D, Edge Article.


Felix N. Ngassa, Shannon M. Biros, Richard J. Staples. “Crystal structure of N-[(1S,2S)-2-aminocyclohexyl]-2,4,6-trimethylbenzenesulfonamideActa Cryst. 2015, E71, 1521-1524.


Tyler A. Cooley,* Sean Riley,* Shannon M. Biros, Richard J. Staples, Felix N. Ngassa. “Crystal structure of 2,4-dinitrophenyl 4-methylbenzene sulfonate: A new polymorphActa Cryst. 2015, E71, 1085-1088.


Tsvetelina P. Atanasova,* Sean Riley,* Shannon M. Biros, Richard J. Staples, Felix N. Ngassa. “Crystal structure of 3,5-dimethylphenyl 2-nitrobenzenesulfonateActa Cryst. 2015, E71, 1045-1047.


Alyssa A. Kulesza,* Richard J. Staples, Shannon M. Biros. “Crystal structure of bis(3,3-dimethyl-2-oxobutyl)diphenyl phosphonium bromide chloroform solvate (1/1)Acta Cryst. 2015, E71, o339-o340.


Erin G. Leach,* Alyssa A. Kulesza,* Richard J. Staples, Shannon M. Biros. “Crystal structures of 1-(4-chlorophenyl)-2-(diphenylphosphoryl)ethan-1-one and 1-(diphenylphosphoryl)-3,3-dimethylbutan-2-one” Acta Cryst. 2015, E71, 523-527.


Hope T. Sartain,* Shelby N. McGraw,* Christopher Lawrence, Eric J. Werner, Shannon M. Biros. “A Novel Tripodal CMPO Ligand: Affinity for f-Elements, Computational Investigations and Luminescence PropertiesInorg. Chim. Acta 2015, 426, 126-135.


Hope T. Sartain,* Richard J. Staples, Shannon M. Biros. “Crystal structure of pentakis (ethylenediamine-[kappa]2N,N')lanthanum(III) trichloride-ethylenediamine (1/1) dichloromethane solvateActa Cryst. 2014, E70, 424-426.


Nathan H. Murray,* Shannon M. Biros, Robert L. LaDuca. “Crystal structure of [propane-1,3-diyldbis(piperidine-4,1-diyl)]bis[(pyridin-4-yl)methanone]-isophthalic acid (1/1)Acta Cryst. 2014, E70, 298-300.


Julie A. Stoscup,* Richard J. Staples, Shannon M. Biros. “Crystal Structure of a Samarium(III) nitrate Chain Cross-linked by a bis-Carbamoylmethylphosphine oxide ligand”, Acta Cryst. 2014, E70, 188-191.


Laurie A. Witucki, William R. Winchester, Shannon M. Biros. “Investigation of 1H NMR Chemical Shift in Various Systems: A Set of Advanced 1D 1H NMR Undergraduate Laboratory Projects”, Chemical Educator, 2014, 19, 471-476.


Shannon M. Biros and Fraser Hof. “Supramolecular Chemistry in Drug Design” in Supramolecular Chemistry: From Molecules to Nanomaterials; Philip A. Gale and Jonathan W. Steed, Eds.; John Wiley & Sons, Ltd: Southern Gate, Chichester, 2012, p 1909-1928.


Pablo Ballester and Shannon M. Biros. "CH-pi and pi-pi Interactions as Contributors to the Guest Binding in Reversible Inclusion and Encapsulation Complexes" in The Importance of Pi-Interactions in Crystal Engineering (Frontiers in Crystal Engineering 3) Edward Tiekink and Julio  Zukerman-Schpector, Eds.; John Wiley & Sons; 2012, p 79-105.


Prior to GVSU:


Julius Rebek, Jr.; Shannon M. Biros; Lionel Moisan; Severin Odermatt. "Oxazole-Pyrrole-Piperazine Alpha-Helix Mimetic" U.S. Patent Appl. Publ., 2009, No. 12/362,934.


Courtney J. Hastings, Michael D. Pluth, Shannon M. Biros, Robert G. Bergman and Kenneth N. Raymond. “Simultaneously Bound Guests and Chiral Recognition: A Chiral Self-Assembled Supramolecular Host Encapsulates Hydrophobic Guests”, Tetrahedron 2008, 64, 8362-8367.


Shannon M. Biros, Robert M. Yeh and Kenneth N. Raymond. “Design and Formation of a Large, Tetrahedral M4L6 Supramolecular Cluster using 1,1’-Binaphthyl Ligands”, Angew. Chem. Int. Ed. 2008, 47, 6062-6064.


Julius Rebek, Jr., Shannon M. Biros, Lionel Moisan, Alessandro Volonterio, Enrique Mann and Trevor Dale. "Pyridazine Based Alpha-Helix Mimetics" International Patent Appl. Publ., 2008, PCT/US2008/009730. 


Julius Rebek, Jr., Shannon M. Biros, Lionel Moisan, Alessandro Volonterio, Enrique Mann and Trevor Dale. "Pyridazine Based Alpha-Helix Mimetics" US Patent Appl. No. 12/228,559, filed Aug. 13, 2008., PCT/US2008/009730.


Julius Rebek, Jr. Shannon M. Biros, Lionel Moisan. "UPP Amphiphilic alpha-Helix Mimetics"  International Patent Appl. Publ., 2008, PCT/US2008/009417.


Shannon M. Biros, Robert G. Bergman and Kenneth N. Raymond. “The Hydrophobic Effect Drives the Recognition of Hydrocarbons by an Anionic Metal-Ligand Cluster”, J. Am. Chem. Soc., 2007, 129, 12094-12095.


Lionel Moisan, Trevor J. Dale, Naran Gombosuren, Shannon M. Biros, Enrique Mann, Jun-Li Hou, Fernando P. Crisostomo and Julius Rebek, Jr. “Facile Synthesis of Pyridazine-Based alpha-Helix Mimetics”, Heterocycles, 2007, 73, 661-671.


Shannon M. Biros, Lionel Moisan, Enrique Mann, Alexandre Carella, Dayong Zhai, John C. Reed and Julius Rebek, Jr.Heterocyclic alpha-Helix Mimetics for Targeting Protein-Protein Interactions, Biorg. Med. Chem. Lett., 2007, 17, 4641-4645.


Shannon M. Biros and Julius Rebek, Jr. “Water-soluble Cavitands and Capsules”, Chem. Soc. Rev., 2007, 36, 93-104. 


Richard J. Hooley, Shannon M. Biros and Julius Rebek, Jr.  “The Use of a Deep, Water-Soluble Cavitand as a Phase-Transfer Catalyst”, Angew. Chem. Int. Ed. 2006, 45, 3517-3519. 


Alasdair M. Barr, Jefferson W. Kinney, Matthew N. Hill, Xiaoying Lu, Shannon M. Biros, Julius Rebek, Jr., Tamas Bartfai. “A Novel, Systemically Active, Selective Galanin Receptor Type-3 Ligand Exhibits Antidepressant-like Activity in Preclinical Tests”, Neurosci. Lett., 2006, 405, 111-115.


Julius Rebek, Jr., Shen Gu and Shannon M. Biros.  “Functionalized Pyridazine Derivatives as Novel Scaffolds for -helix Mimicry, and their Preparation and Pharmaceutical Composition” US Patent Appl. Publ., 2006, US 2006205728. 


Shen Gu, Shannon M. Biros and Julius Rebek, Jr.  “Novel Scaffolds for alpha-helix Mimicry”, US Patent Application Number 60/660,939, filed Mar. 03, 2006


Richard J. Hooley, Shannon M. Biros and Julius Rebek, Jr.  “Normal Hydrocarbons Tumble Rapidly in a Deep, Water-Soluble Cavitand”, Chem. Commun. 2005, 509-510.


Clemens H. Haas, Shannon M. Biros and Julius Rebek, Jr. “Binding Properties of Cavitands in Aqueous Solution – The Effect of Charge on Guest Selectivity”, Chem. Commun. 2005, 6044-6045. 


Shannon M. Biros, Elke C. Ullrich, Fraser Hof, Laurent Trembleau, and Julius Rebek, Jr.  “Kinetically Stable Complexes in Water: The Role of Hydration and Hydrophobicity”, J. Am. Chem. Soc. 2004, 126, 2870-2876. 


Shannon M. Biros,* Brian M. Bridgewater, Adriel Villeges-Estrada, Joseph Tanski, Gerard Parkin.  “Antimony Ethylene Glycolate and Catecholate Compounds: Structural Characterization of Polyesterification Catalysts”, Inorg. Chem., 2002, 41, 4051-4057.