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Department of Chemistry Cliff Berkman

Cliff Berkman



Fulmer 477
Pullman, WA 99164-4630

(509) 335-7613




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


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




Dr. Cliff Berkman


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. One of major efforts is aimed at the prostate cancer enzyme-biomarker known as prostate-specific membrane antigen. Some of this technology is being advanced towards the development of marketable diagnostic and therapeutic drugs through the startup company Cancer Targeted Technology (CTT).

We are also interested in the design and synthesis of phosphorylated peptides as a pro-prodrug scaffold requiring activation by carboxypeptidases. Such molecules require a primary bioactivation step in which the peptide is cleaved by a carboxypeptidase and the resulting N-terminal phosphorylated amino acid self-activates to eject a drug.

Recent Publications

  • The Molecular Pruning of a Phosphoramidate Inhibitor of Prostate-Specific Membrane Antigen. Wu, L.Y.; Anderson, M.O.; Toriyabe, Y.; Maung, J.*; Campbell, T.Y.; Tajon, C.; Kazak, M.*; Moser, J.*; Berkman, C.E. Bioorg. Med. Chem. 200715, 7434.
  • 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.  Bioorg. Med. Chem. Lett. 200818, 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 200868, 955.
  • Pseudoirreversible Inhibition of Prostate-Specific Membrane Antigen by Phosphoramidate Peptidomimetics. Liu, T.; Toriyabe, Y.; Kazak, M.*; Berkman, C.E.  Biochemistry 200847, 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 200969, 585.
  • Assessment of an 18F-labeled phosphoramidate peptidomimetic as a new prostate-specific membrane antigen-targeted imaging agent for prostate cancer.  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.  J. Nuc. Med. 200950, 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 201070, 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. 201051, 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.  Int. J. Oncol. 201036, 777.
  • Prostate Specific Membrane Antigen-Targeted Photodynamic Therapy Induces Rapid Cytoskeletal Disruption. Liu, T.; Wu, L.Y.; Berkman, C.E.  Cancer Lett2010296, 106.
  • A Targeted Low Molecular Weight Near-Infrared Fluorescent Probe for Prostate Cancer. Liu, T.; Wu, L.Y.; Choi, J.K.*; Hopkins, M.R.*; Berkman, C.E.  Bioorg. Med. Chem. Lett201020, 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 201171, 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. Chem. Biol. Drug. Des. 201177, 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. Int. J. Oncol201138, 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. Angew. Chem. Int. Ed. 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. Bioorg. 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.  Chem. Comm.  2011, 4712846.
  • 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.  Anal. 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.; Bryan, J.N.; Berkman, C.E. The Prostate201272, 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. Bioorg. Med. Chem. Lett. 201222, 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 201272, 1532.
  • Prolonged androgen deprivation leads to down-regulation of androgen receptor and prostate-specific membrane antigen in prostate cancer cells. Liu, T.; Wu, L.Y.; Fulton, M.D.*; Johnson, J.M.*; Berkman, C.E. Int. J. Oncol2012, 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. 2012 (in press, PMID: 22911263, doi: 10.1002/pros.22575).
  • 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. Bioorg. Med. Chem. Lett. 2012 (doi: 10.1016/j.bmcl.2012.11.015)


Current Group Members

Research Asst. Prof:  Tiancheng Liu (molecular biology)

Postdoctoral Researchers:  Lisa Wu PhD

Grad Students:  Brian Backer, Paul Olatunji, Michael Pun, Bradley Roberts, Dawanna White

Undergrad Research Assistants: Melody Fulton, Jacqueline Johnson, Nathan Beattie, Matt Galliher, James Kent, Andrew Arndt, Adrienne Wilen

Recent Alumni:  Jessie Byers, Mark Hopkins, Joe Choi, Cindy Choy, Nina Ganguly, Jonathan Geruntho, Desiree Mendes, Cory Ley, Brandan Cook, Kamal Seneviratne