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Department of Chemistry Cliff Berkman

Cliff Berkman

 

Professor

Fulmer 477
Pullman, WA 99164-4630

(509) 335-7613
cberkman@wsu.edu

 

Education

Ph.D. Chemistry, 1993
Loyola University of Chicago, Chicago, IL

B.A. Chemistry (Honors), 1986
Lake Forest College, Lake Forest, IL

 

 

cliff

Dr. Cliff Berkman

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Research

A major emphasis of the research in my lab is aimed at the design, synthesis, and evaluation of inhibitors of proteases and peptidases related to cancer. More specifcally, we are interested in the design of novel enzymes inhibitors for the use in targeting tumor cells with diagnostic and therapeutic agents. We are leaders in the field that is focused on inhibitors of the prostate cancer enzyme-biomarker known as prostate-specific membrane antigen (PSMA). Some of this technology has advanced through clinical trials for marketable diagnostic and therapeutic drugs through our startup company Cancer Targeted Technology (CTT).

We are also interested in the development of phosphorylated amino acids as pro-prodrug scaffolds for controlled release applications such as L-Dopa, small-molecule drug conjugates (SMDCs), and cellular trafficking turn-on probes.

Recent Publications from Research at WSU

  • Phosphoramidate Derivatives Of Hydroxysteriods As Inhibitors Of Prostate-Specific Membrane Antigen. Wu, L.Y.; Do, J.*; Kazak, M.*; Page, H.*; Toriyabe, Y. Anderson, M.O.; Berkman, C.E. Med. Chem. Lett. 2008, 18, 281.
  • Cell-Surface Labeling and Internalization by a Fluorescent Inhibitor of Prostate-Specific Membrane Antigen. Liu, T.; Wu, L.Y.; Kazak, M.*; Berkman, C.E. The Prostate 2008, 68, 955.
  • Pseudoirreversible Inhibition of Prostate-Specific Membrane Antigen by Phosphoramidate Peptidomimetics. Liu, T.; Toriyabe, Y.; Kazak, M.*; Berkman, C.E. Biochemistry 2008, 47, 12658.
  • In Vitro Targeted Photodynamic Therapy with a Pyropheophorbide-a Conjugated Inhibitor of Prostate Specific Membrane Antigen. Liu, T.; Wu, L.Y.; Choi, J.K.*; Berkman, C.E. The Prostate 2009, 69,
  • Synthesis and in vivo evaluation of a [18F]-labeled phosphoramidate for imaging of PSMA expression. Lapi, S.E; Wu, L.Y.; Wahnishe, H.; Pham, D.; Nedrow-Byers, J.R.; Liu, T.; VanBrocklin, H.F.; Berkman, C.E.; Jones, E.F. Nuc. Med. 2009, 50, 2042.
  • Expression of Prostate-Specific Membrane Antigen (PSMA), increases cell folate uptake and proliferation and suggests a novel role for PSMA in the uptake of the non-polyglutamated folate, folic acid. Yao, V.; Berkman, C.E.; Choi, J.K.*; O’Keefe, D.S.; Bacich, D.J. The Prostate 2010, 70, 305.
  • A Simple Method for the Oxidation of a-Amino Acids Esters to a-Oximino Esters. Wu, L.Y.; Choi, J.K.*; Hatton, K.Y.; Berkman, C.E. Tetrahedron Lett. 2010, 51, 402.
  • Targeted Photodynamic Therapy for Prostate Cancer: Inducing Apoptosis via Activation of the Caspase-8/3 Cascade Pathway. Liu, T.; Wu, L.Y.; Choi, J.K.*; Berkman, C.E. J. Oncol. 2010, 36, 777.
  • Prostate Specific Membrane Antigen-Targeted Photodynamic Therapy Induces Rapid Cytoskeletal Disruption. Liu, T.; Wu, L.Y.; Berkman, C.E. Cancer Lett. 2010, 296, 106.
  • A Targeted Low Molecular Weight Near-Infrared Fluorescent Probe for Prostate Cancer. Liu, T.; Wu, L.Y.; Hopkins, M.R.*; Choi, J.K.*; Berkman, C.E. Med. Chem. Lett. 2010, 20, 7124.
  • Flow Cytometric Detection of Prostate Tumor Cells Using Chemoaffinity Labels. Wu, L.Y.; Liu, T.; Grimm, A.L.; Davis, W.C.; Berkman, C.E. The Prostate 2011, 71, 52.
  • N-Substituted Glutamyl Sulfonamides As Inhibitors Of Glutamate Carboxypeptidase II (GCP2). Blank, B.*; Alayoglu, P.; Engen,W.; Choi, J.K.*; Berkman, C.E.; Anderson, M.O. Biol. Drug. Des. 2011, 77, 241.
  • Detection of Prostate-Specific Membrane Antigen on HUVECs in Response to Breast Tumor-Conditioned Medium. Liu, T.; Jabbes, M.; Nedrow-Byers, J.; Wu, L.Y.; Bryan, J.N.; Berkman, C.E. J. Oncol. 2011, 38, 1349.
  • Capture and Visualization of Hydrogen Sulfide via A Fluorescent Probe. Liu, C.; Pan, J.; Li, S.; Zhao, Y.; Wu, L.Y.; Berkman, C.E.; Whorton, A.R.; Xian, M. Chem. 2011, 50, 10327.
  • Spacer Length Effects on In Vitro Imaging and Surface Accessibility of Fluorescent Inhibitors of Prostate Specific Membrane Antigen. Liu, T.; Nedrow-Byers, J.R. Hopkins, M.R*.; Berkman, C.E. Med. Chem. Lett. 2011, 21, 7013.
  • Investigation of the hydrazide/hydrazone click reaction as a biomolecule labeling strategy with M(CO)3 (M = Re, 99mTc). Ganguly, T; Kasten, B; Bucar, D-K; MacGillivray, L.; Berkman, C.E.; Benny, P. Comm. 2011, 47, 12846.
  • High Resolution Time-of-Flight Mass Analysis of the Entire Range of Intact Singly-Charged Proteins. Lee, J.; Chen, H.; Liu, T.; Berkman, C.E.: Reilly, P.T.A. Chem. 2011, 83, 9406.
  • A phosphoramidate-based prostate-specific membrane antigen-targeted SPECT agent. Nedrow-Byers, J.; Jewett, C.*; Jabbes, M.; He, H.; Liu, T.; Benny, P.A.; Bryan, J.N.; Berkman, C.E. The Prostate. 2012, 72, 904.
  • Targeting Prostate Cancer Cells with a Multivalent PSMA Inhibitor-Guided Streptavidin Conjugate. Liu,T.; Nedrow-Byers, J.R.; Hopkins, M.R.*; Wu, L.Y.; Lee, J.; Reilly, P.T.A.; Berkman, C.E. Med. Chem. Lett. 2012, 22, 3931.
  • Chemoaffinity Capture of Pre-Targeted Prostate Cancer Cells on Magnetic Beads. Wu, L.Y.; Liu, T.; Hopkins, M.R.*; Davis, W.C.; Berkman, C.E. The Prostate 2012, 72, 1532.
  • Prolonged androgen deprivation leads to down-regulation of androgen receptor and prostate-specific membrane antigen in prostate cancer cells. Liu, ; Wu, L.Y.; Fulton, M.D.*; Johnson, J.M.*; Berkman, C.E. Int. J. Oncol. 2012, 41, 2087.
  • PSMA-targeted SPECT agents: Mode of Binding effect on in vitro Performance. Nedrow-Byers, J.R.; Moore, A.L.; Ganguly, T.; Hopkins, M.R.*; Fulton, M.D.*; Benny, P.D.; Berkman, C.E. The Prostate. 2013, 73, 355.
  • Targeting Prostate Cancer Cells with PSMA Inhibitor-Guided Gold Nanoparticles. Kasten, B.B.; Liu, T.; Nedrow-Byers, J.R.; Benny, P.D.; Berkman, C.E. Med. Chem. Lett. 2013, 23, 565.
  • Rationally Designed Sulfamides As Glutamate Carboxypeptidase II (GCPII) Inhibitors. Choy, C.J.; Fulton, M.D.*; Davis, A.L.*; Hopkins, M.R.* Choi, J.K.*; Anderson,M.O.; Berkman, C.E. Biol. Drug. Des. 2013, 82, 612.
  • From AR to c-MET: Androgen Deprivation Leads to a Signaling Pathway Switch in Prostate Cancer Cells. Liu, T.; Mendes, D.E.; Berkman, C.E. J. Oncol. 2013, 43, 1125.
  • Prolonged Androgen Deprivation Leads to Overexpression of Calpain 2: Implications for Prostate Cancer Progression. Liu, T.; Mendes, D.E.; Berkman, C.E. J. Oncol. 2014, 44, 467.
  • Functional Prostate-Specific Membrane Antigen is Enriched in Exosomes from Prostate Cancer Cells. Liu, T.; Mendes, D.E.; Berkman, C.E. J. Oncol. 2014, 44, 918.
  • Biochemical Characterization of Prostate-Specific Membrane Antigen from Canine Prostate Carcinoma Cells. Wu, L.Y.; Johnson, J.M.*; Simmons, J.K.; Mendes, D.E.; Geruntho, J.G.; Liu, T.; Dirksen, W.P.; Rosol, T.J.; Davis, W.C.; Berkman, C.E. The Prostate, 2014, 74, 451.
  • Chemoenzymatic Resolution of (S)-Malathion. Hitta, D.M.; Yamina Belabassi, Suhy, J.; Berkman, C.E.; Thompson, C.M. Tetrahedron: Asymmetry. 2014, 25, 529.
  • Development of Inhibitor-Directed Enzyme Prodrug Therapy (IDEPT) for Prostate Cancer. Martin, S.E.; Ganguly, T.; Munske, G.R.; Fulton, M.D.; Hopkins, M.R.; Berkman, C.E.; Black, M.E. Bioconjugate Chem. 2014, 25, 1752.
  • Targeting PSMA with a 64Cu-labeled phosphoramidate inhibitor for PET/CT imaging of variant PSMA-expressing xenografts in a mouse model of prostate cancer. Nedrow, J.; Latoche, J.; Day, K.; Ganguly, T.; Zeng, D.; Berkman, C.; Anderson, C.J. Nuc. Med. 2014, 55(Meeting Abstracts),
  • Synthesis and Evaluation of Constrained Phosphoramidate Inhibitors of Prostate-Specific Membrane Antigen. Ley, C.R.; Beattie, N.R.; Dannoon, S.; Regan, M.; VanBrocklin, H.F.; Berkman, C.E. Med. Chem. Lett. 2015, 25, 2536.
  • A high affinity [18F]labeled phosphoramidate peptidomimetic PSMA-targeted inhibitor for PET imaging of prostate cancer. Ganguly, T.; Dannoon, S.; Hopkins, M.R.; Murphy, S.; Cahaya, H.; Blecha, J.E.; Jivan, S.; Drake, C.R.; Barinka C.; Jones, E. F.; VanBrocklin, H.F.; Berkman, C.E. Nucl. Med. Biol. 2015, 42, 780.
  • Phosphoramidate-Based Peptidomimetic Inhibitors of Membrane Type-1 Matrix Metalloproteinase. Mendes, D.E.; Wong-On-Wing, A.; Berkman, C.E. Enz. Inhib. Med. Chem. 2015, 31, 167 (DOI:10.3109/14756366.2015.1010528).
  • Targeting PSMA with a 64Cu-labeled phosphoramidate inhibitor for PET/CT imaging of variant PSMA-expressing xenografts in mouse models of prostate cancer. Nedrow, J.R.; Day, K.E.; Latoche, J.D.; Modi, J.; Ganguly, T.; Zeng, D.; Kurland, B.F.; Berkman, C.E.; Anderson, C.J. Imaging Biol. 2016 18, 402 (doi: 10.1007/s11307-015-0908-7)
  • Design of composite inhibitors targeting glutamate carboxypeptidase II: the importance of effector functionalities. Novakova, Z.; Cerny, J.; Choy, C.J.; Nedrow, J.R.; Choi, J.K.; Berkman, C.E.; Barinka, C. FEBS J. 2016, 283, 130 (doi: 10.1111/febs.13557).
  • A Method to Determine the Mode of Binding for Glutamate Carboxypeptidase II Inhibitors using Biolayer Interferometry. Choy, C.J. and Berkman, C.E. Enz. Inhib. Med. Chem. 2016 Feb 12, 1-4 (DOI:10.3109/14756366.2015.1132208).
  • A Tunable pH-Sensitive Linker for Controlled Release. Choy, C.J.; Geruntho, J.J.; Davis, A.L.; Berkman, C.E. Bioconjugate Chem. 2016, 27, 824.
  • Structure-Activity Relationship of 18F-labeled phosphoramidate peptidomimetic Prostate-Specific Membrane Antigen (PSMA)-targeted inhibitor analogues for PET imaging of prostate cancer. Dannoon, S.; Ganguly, T.; Cahaya, H.; Geruntho, J.; Galliher, M.; Beyer, S.; Choy, C.; Hopkins, M.; Regan, M.; Blecha, J.; Skultetyova, L.; Drake, C.; Jivan, S.; Barinka, C.; Jones, E.; Berkman, C.E.; VanBrocklin, H. J Med Chem. 2016, 59, 5684.
  • Second-Generation of Tunable pH-Sensitive Phosphoramidate-Based Linkers for Controlled Release. Choy, C.J.; Ley, C.R.; Davis, A.L.; Backer, B.S.; Geruntho, J.J.; Clowers, B.H.; Berkman, C.E. Bioconjugate Chem. 2016, 27, 2206.
  • Development of a Novel PSMA-targeted PET imaging Agent, CTT1057, for use in Prostate Cancer. Langton-Webster, B.; Berkman, C.; Slater, J.; Jivan, S.; Neumann, K.; Whalley, E.; Ketteridge, P.; Behr, S.; Aggarwal, R.; VanBrocklin, H. Nuc. Med. 2016. 57(supplement 2), 467.
  • Silica Nanostructured Platform for Affinity Capture of Tumor-Derived Exosomes. Parissa Z.; Geruntho, J.J.; Marin-Flores, O.; Berkman, C.E., Norton, M.G. Mater. Sci. 2017, 52, 6907.
  • 177Lu-Labeled Phosphoramidate-Based PSMA Inhibitors: The Effect of an Albumin Binder on Biodistribution and Therapeutic Efficacy in Prostate Tumor-Bearing Mice. Choy, C.J.; Ling, X.; Geruntho, J.J.; Beyer, S.K.; Latoche, J.D.; Langton-Webster, B.; Anderson, C.J.; Berkman, C.E. Theranostics 2017, 7, 1928.
  • more to come…