David Perrin

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David Perrin

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Research and Teaching Interests

CATALYSIS AND MOLECULAR RECOGNITION APPLIED TO BIOLOGY RESEARCH THEME: My research uses the tools of synthetic chemistry to address questions of molecular recognition and catalysis within a biological setting, all the while maintaining medically relevant goals. I provide a comprehensive research program at the interface of chemistry and biology, and preliminary data for these projects have already appeared in first-rate peer reviewed journals.

KEY WORDS: Radiopharmaceuticals, natural product libraries, chemical biology, DNA recognition, self-assembly, synthetic DNAzymes, enzyme mimics, Protein Evolution.

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MOLECULAR RECOGNITION IN CHEMICAL BIOLOGY [PDF]

Perrin Group Winter 2007

Winter Holiday 2007

 

Contact

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Office Room Number(s): 
A343
Office Phone Number: 
604-822-0567
Office Hours: 
Wednesday Afternoons

Publications

2015

Pourghiasian, M. ; Liu, Z. ; Pan, J. ; Zhang, Z. ; Colpo, N. ; Lin, K. S. ; Perrin, D. M. ; Benard, F. (18)F-Ambf3-Mj9: A Novel Radiofluorinated Bombesin Derivative For Prostate Cancer Imaging}. Bioorg. Med. Chem. 2015, 23, 1500–1506.
Liu, Z. ; Chao, D. ; Li, Y. ; Ting, R. ; Oh, J. ; Perrin, D. M. From Minutes To Years: Predicting Organotrifluoroborate Solvolysis Rates}. Chemistry 2015, 21, 3924–3928.
Liu, Z. ; Amouroux, G. ; Zhang, Z. ; Pan, J. ; Hundal-Jabal, N. ; Colpo, N. ; Lau, J. ; Perrin, D. M. ; Benard, F. ; Lin, K. S. (18)F-Trifluoroborate Derivatives Of [Des-Arg(10)]Kallidin For Imaging Bradykinin B1 Receptor Expression With Positron Emission Tomography}. Mol. Pharm. 2015, 12, 974–982.
Renders, M. ; Miller, E. ; Hollenstein, M. ; Perrin, D. A Method For Selecting Modified Dnazymes Without The Use Of Modified Dna As A Template In Pcr. Chem. Commun. (Camb.) 2015, 51, 1360–1362.
Liu, E. ; Lam, C. H. ; Perrin, D. M. Synthesis And Enzymatic Incorporation Of Modified Deoxyuridine Triphosphates}. Molecules 2015, 20, 13591–13602.
Azadbakht, T. ; Zolfigol, M. Ali; Azadbakht, R. ; Khakyzadeh, V. ; Perrin, D. M. C(Sp2)-C(Sp2) Cross Coupling Reaction Catalyzed By A Water-Stable Palladium Complex Supported Onto Nanomagnetite Particles. New J. Chem. 2015, 39, 439-444.
Zhang, Z. ; Dude, I. ; Jenni, S. ; Liu, Z. (Zippo); Hundal-Jabal, N. ; Colpo, N. ; Perrin, D. ; Lin, K. - S. ; Bénard, F. Radiosynthesis And Evaluation Of 18F-Ambf3-Toc For Imaging Somatostatin Receptor With Positron Emission Tomography. Journal of Nuclear Medicine 2015, 56, 1136.
Zhang, Z. ; Jenni, S. ; Liu, Z. (Zippo); Hundal-Jabal, N. ; Colpo, N. ; Perrin, D. ; Lin, K. - S. ; Bénard, F. 18F-Ambf3-Phosphonium Cations For Myocardial Perfusion Imaging With Positron Emission Tomography. Journal of Nuclear Medicine 2015, 56, 1081.
Perrin, D. ; Lin, K. - S. ; Bénard, F. ; Yapp, D. ; Liu, Z. ; Pourghiasian, M. ; Lau, J. ; Zhang, Z. ; Jenni, S. A New 18F-Rbf3 Radioprosthetic For One Step Aqueous Labeling Of Peptides And Other Ligands: Meeting The Challenge Of Radiosynthetic Ease And Preclinical Impact I.e. High Specific Activity And High T:nt Ratios. Journal of Nuclear Medicine 2015, 56, 223.
Liu, Z. ; Li, Y. ; Ting, R. ; Perrin, D. M. Designing Kinetically Stable Aryltrifluoroborates As 18F-Capture Agents For Pet Imaging. Journal of Physical Organic Chemistry 2015, 28, 210–214.
Zhao, L. ; May, J. P. ; Blanc, A. ; Dietrich, D. J. ; Loonchanta, A. ; Matinkhoo, K. ; Pryyma, A. ; Perrin, D. M. Synthesis Of A Cytotoxic Amanitin For Biorthogonal Conjugation}. Chembiochem 2015, 16, 1420–1425.

2014

Zolfigol, M. Ali; Azadbakht, T. ; Khakyzadeh, V. ; Nejatyami, R. ; Perrin, D. M. C(Sp2)-C(Sp2) Cross Coupling Reactions Catalyzed By An Active And Highly Stable Magnetically Separable Pd-Nanocatalyst In Aqueous Media. RSC Adv. 2014, 4, 40036-40042.
Liu, Z. ; Hundal-Jabal, N. ; Wong, M. ; Yapp, D. ; Lin, K. - S. ; Benard, F. ; Perrin, D. M. A New 18F-Heteroaryltrifluoroborate Radio-Prosthetic With Greatly Enhanced Stability That Is Labelled By 18F-19F-Isotope Exchange In Good Yield At High Specific Activity. Med. Chem. Commun. 2014, 5, 171-179.
Borderud, S. P. ; Li, Y. ; Burkhalter, J. E. ; Sheffer, C. E. ; Ostroff, J. S. Electronic Cigarette Use Among Patients With Cancer: Characteristics Of Electronic Cigarette Users And Their Smoking Cessation Outcomes. Cancer 2014, 120, 3527–3535.
Liu, Z. ; Pourghiasian, M. ; Radtke, M. Alex; Lau, J. ; Pan, J. ; Dias, G. M. ; Yapp, D. ; Lin, K. - S. ; Bénard, F. ; Perrin, D. M. An Organotrifluoroborate For Broadly Applicable One-Step 18F-Labeling. Angewandte Chemie International Edition 2014, 53, 11876–11880.
Lozada, J. ; Liu, Z. ; Perrin, D. M. Base-Promoted Protodeboronation Of 2,6-Disubstituted Arylboronic Acids}. J. Org. Chem. 2014, 79, 5365–5368.
Liu, Z. ; Pourghiasian, M. ; Benard, F. ; Pan, J. ; Lin, K. S. ; Perrin, D. M. Preclinical Evaluation Of A High-Affinity 18F-Trifluoroborate Octreotate Derivative For Somatostatin Receptor Imaging}. J. Nucl. Med. 2014, 55, 1499–1505.

2013

Dyrager, C. ; Liu, Z. ; Li, Y. ; Perrin, D. M. Synthesis Of A Fluorescent And 18E-Labeled Psma Inhibitor For Targeted Imaging Of Prostate Cancer. BIOPOLYMERS 2013, 100, 293-294.
Liu, Z. ; Li, Y. ; Lozada, J. ; Schaffer, P. ; Adam, M. J. ; Ruth, T. J. ; Perrin, D. M. Stoichiometric Leverage: Rapid 18F-Aryltrifluoroborate Radiosynthesis At High Specific Activity For Click Conjugation. Angewandte Chemie International Edition 2013, 52, 2303–2307.
Liu, Z. ; Li, Y. ; Lin, K. - S. ; Yapp, D. ; Perrin, D. Novel 18F-Radiolabeling Of Rgd At Super High Specific Activity By Isotope Exchange. BIOPOLYMERS 2013, 100, 295.
Hollenstein, M. ; Hipolito, C. J. ; Lam, C. H. ; Perrin, D. M. Toward The Combinatorial Selection Of Chemically Modified Dnazyme Rnase A Mimics Active Against All-Rna Substrates. ACS Combinatorial Science 2013, 15, 174-182.
Liu, Z. ; Li, Y. ; Lozada, J. ; Wong, M. Q. ; Greene, J. ; Lin, K. S. ; Yapp, D. ; Perrin, D. M. Kit-Like 18F-Labeling Of Rgd-19F-Arytrifluroborate In High Yield And At Extraordinarily High Specific Activity With Preliminary In Vivo Tumor Imaging}. Nucl. Med. Biol. 2013, 40, 841–849.
Li, Y. ; Liu, Z. ; Lozada, J. ; Wong, M. Q. ; Lin, K. S. ; Yapp, D. ; Perrin, D. M. Single Step 18F-Labeling Of Dimeric Cyclorgd For Functional Pet Imaging Of Tumors In Mice}. Nucl. Med. Biol. 2013, 40, 959–966.
Largy, E. ; Liu, W. ; Hasan, A. ; Perrin, D. M. Base-Pairing Behavior Of A Carbocyclic Janus-At Nucleoside Analogue Capable Of Recognizing A And T Within A Dna Duplex}. Chembiochem 2013, 14, 2199–2208.
Li, Y. ; Schaffer, P. ; Perrin, D. M. Dual Isotope Labeling: Conjugation Of 32P-Oligonucleotides With 18F-Aryltrifluoroborate Via Copper(I) Catalyzed Cycloaddition}. Bioorg. Med. Chem. Lett. 2013, 23, 6313–6316.
Li, Y. ; Guo, J. ; Tang, S. ; Lang, L. ; Chen, X. ; Perrin, D. M. One-Step And One-Pot-Two-Step Radiosynthesis Of Cyclo-Rgd-(18)F-Aryltrifluoroborate Conjugates For Functional Imaging}. Am J Nucl Med Mol Imaging 2013, 3, 44–56.
Li, Y. ; Liu, Z. ; Harwig, C. W. ; Pourghiasian, M. ; Lau, J. ; Lin, K. S. ; Schaffer, P. ; Benard, F. ; Perrin, D. M. (18)F-Click Labeling Of A Bombesin Antagonist With An Alkyne-(18)F-Arbf(3) (-): In Vivo Pet Imaging Of Tumors Expressing The Grp-Receptor}. Am J Nucl Med Mol Imaging 2013, 3, 57–70.
Zhibo, L. ; Ying, L. ; Lozada, J. ; Wang, M. ; Kuo-shyan, L. ; Yepp, D. ; Perrin, D. Novel F-18-Radiolabeling Of Rgd At Super High Specific Activity By Isotope Exchange. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS 2013, 56, S167.
Zhibo, L. ; Kuo-shyan, L. ; Schaffer, P. ; Perrin, D. ``kit'' F-18-Radiolabeling Based On B-F Bond Formation. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS 2013, 56, S166.
Li, Y. ; Liu, Z. ; Wang, M. ; Lozada, J. ; Lin, K. - S. ; Yapp, D. ; Bénard, F. ; Perrin, D. One Step F-18-Labeling Of Complex Peptides For Functional Pet Imaging. BIOPOLYMERS 2013, 100, 242.
Zhao, L. ; Dietrich, D. ; Perrin, D. Synthesis Of ``smart Drug'': Amanitin Conjugates. BIOPOLYMERS 2013, 100, 263.

2012

Perrin, D. M. ; Hollenstein, M. ; Lam, C. H. ; Hipolito, C. J. Enhancing Catalytic Activity Of Nucleic Acids By Making Them More Protein Like. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY 2012, 243.
Perrin, D. M. ; Li, Y. ; Ting, R. ; Harwig, C. W. ; Keller, U. Auf Dem; Bellac, C. L. ; Lange, P. F. ; Inkster, J. A. H. ; Schaffer, P. ; Adam, M. J. ; Ruth, T. J. ; Overall, C. M. ; Bénard, F. Rapid, One Step Aqueous 18F-Labeling Of Peptides For Pet Imaging. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY 2012, 243.
Perrin, D. M. ; Li, Y. ; Ting, R. ; Harwig, C. W. ; Keller, U. Auf Dem; Bellac, C. L. ; Lange, P. F. ; Inkster, J. A. H. ; Schaffer, P. ; Adam, M. J. ; Ruth, T. J. ; Bénard, F. ; Overall, C. M. One-Step 18F-Labeling Of Marimastat, A Clinically Trialed Drug, To Image Breast Cancer Associated Matrix Metalloproteases In Mice. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY 2012, 243.
Zhao, L. ; May, J. P. ; Huang, J. ; Perrin, D. M. Stereoselective Synthesis Of Brevianamide E. Org. Lett. 2012, 14, 90-93.
Liu, Z. ; Li, Y. ; Lozada, J. ; Pan, J. ; Lin, K. - S. ; Schaffer, P. ; Perrin, D. M. Rapid, One-Step, High Yielding 18F-Labeling Of An Aryltrifluoroborate Bioconjugate By Isotope Exchange At Very High Specific Activity. Journal of Labelled Compounds and Radiopharmaceuticals 2012, 55, 491–496.

2011

Lam, C. H. ; Hipolito, C. J. ; Hollenstein, M. ; Perrin, D. M. A Divalent Metal-Dependent Self-Cleaving Dnazyme With A Tyrosine Side Chain. Org. Biomol. Chem. 2011, 9, 6949-6954.
Li, Y. ; Ting, R. ; Harwig, C. W. ; Keller, Uauf dem; Bellac, C. L. ; Lange, P. F. ; Inkster, J. A. H. ; Schaffer, P. ; Adam, M. J. ; Ruth, T. J. ; Overall, C. M. ; Perrin, D. M. Towards Kit-Like 18F-Labeling Of Marimastat, A Noncovalent Inhibitor Drug For In Vivo Pet Imaging Cancer Associated Matrix Metalloproteases. Med. Chem. Commun. 2011, 2, 942-949.

2010

Perrin, D. M. ; Ting, R. ; Harwig, C. ; Li, Y. Arylboronic Acids As Captors Of Aqueous 18F-Fluoride For The One Step Labeling Of Biomolecules Suitable For Pet Imaging. In; American Chemical Society, 2010; p. ORGN-430.
Keller, Uauf dem; Bellac, C. L. ; Li, Y. ; Lou, Y. ; Lange, P. F. ; Ting, R. ; Harwig, C. ; Kappelhoff, R. ; Dedhar, S. ; Adam, M. J. ; Ruth, T. J. ; Benard, F. ; Perrin, D. M. ; Overall, C. M. Novel Matrix Metalloproteinase Inhibitor [18F]Marimastat-Aryltrifluoroborate As A Probe For In Vivo Positron Emission Tomography Imaging In Cancer. Cancer Research 2010, 70, 7562 - 7569.
Perrin, D. M. ; Hollenstein, M. ; Lam, C. H. ; Hipolito, C. J. Synthetic Rna-Cleaving Dnazymes With Three Protein Side Chains: Amines, Imidazoles, And Guanidines. In; American Chemical Society, 2010; p. BIOT-303.

2009

Keller, U. A. D. ; Lou, Y. M. ; Ting, R. ; Harwig, C. ; Prudova, A. ; Dedhar, S. ; Perrin, D. M. ; Overall, C. M. Substrate Degradomics And Activity Imaging Of Matrix Metalloproteinases In Breast Carcinogenesis. Clinical & Experimental Metastasis 2009, 26, 866-866.
Thomas, J. M. ; Perrin, D. M. Probing General Acid Catalysis In The Hammerhead Ribozyme. Journal of the American Chemical Society 2009, 131, 1135-1143.
Hollenstein, M. ; Hipolito, C. J. ; Lam, C. H. ; Perrin, D. M. A Dnazyme With Three Protein-Like Functional Groups: Enhancing Catalytic Efficiency Of M2+-Independent Rna Cleavage. Chembiochem 2009, 10, 1988-1992.
Li, Y. ; Asadi, A. ; Perrin, D. M. Hydrolytic Stability Of Nitrogenous-Heteroaryltrifluoroborates Under Aqueous Conditions At Near Neutral Ph. Journal of Fluorine Chemistry 2009, 130, 377-382.
Thomas, J. M. ; Yoon, J. K. ; Perrin, D. M. Investigation Of The Catalytic Mechanism Of A Synthetic Dnazyme With Protein-Like Functionality: An Rnasea Mimic?. Journal of the American Chemical Society 2009, 131, 5648-5658.
Hollenstein, M. ; Hipolito, C. J. ; Lam, C. H. ; Perrin, D. M. A Self-Cleaving Dna Enzyme Modified With Amines, Guanidines And Imidazoles Operates Independently Of Divalent Metal Cations (M2+). Nucleic acids research 2009, 37, 1638-49.

2008

Ting, R. ; Harwig, C. W. ; Lo, J. ; Li, Y. ; Adam, M. J. ; Ruth, T. J. ; Perrin, D. M. Substituent Effects On Aryltrifluoroborate Solvolysis In Water: Implications For Suzuki-Miyaura Coupling And The Design Of Stable F-18-Labeled Aryltrifluoroborates For Use In Pet Imaging. Journal of Organic Chemistry 2008, 73, 4662-4670.
Hollenstein, M. ; Hipolito, C. ; Lam, C. ; Dietrich, D. ; Perrin, D. M. A Highly Selective Dnazyme Sensor For Mercuric Ions. Angewandte Chemie-International Edition 2008, 47, 4346-4350.
Ting, R. ; Harwig, C. ; U. Keller, aufdem; McCormick, S. ; Austin, P. ; Overall, C. M. ; Adam, M. J. ; Ruth, T. J. ; Perrin, D. M. Toward [F-18]-Labeled Aryltrifluoroborate Radiotracers: In Vivo Positron Emission Tomography Imaging Of Stable Aryltrifluoroborate Clearance In Mice. Journal of the American Chemical Society 2008, 130, 12045-12055.
Asadi, A. ; Patrick, B. O. ; Perrin, D. M. G(Boolean And)C Quartet - A Dna-Inspired Janus-Gc Heterocycle: Synthesis, Structural Analysis, And Self-Organization. Journal of the American Chemical Society 2008, 130, 12860-+.
Lam, C. ; Hipolito, C. ; Perrin, D. M. Synthesis And Enzymatic Incorporation Of Modified Deoxyadenosine Triphosphates. European Journal of Organic Chemistry 2008, 4915-4923.
Thomas, J. M. ; Perrin, D. M. Probing General Base Catalysis In The Hammerhead Ribozyme. Journal of the American Chemical Society 2008, 130, 15467-15475.
Ting, R. ; Lo, J. ; Adam, M. J. ; Ruth, T. J. ; Perrin, D. M. Capturing Aqueous [F-18]-Fluoride With An Arylboronic Ester For Pet: Synthesis And Aqueous Stability Of A Fluorescent [F-18]-Labeled Aryltrifluoroborate. Journal of Fluorine Chemistry 2008, 129, 349-358.

2007

Asadi, A. ; Patrick, B. O. ; Perrin, D. M. Janus-At Bases: Synthesis, Self-Assembly, And Solid State Structures. Journal of Organic Chemistry 2007, 72, 466-475.
Dietrich, D. ; Perrin, D. M. Preparation Of Photocaged Derivatives Of Alpha-Amanitin. Biopolymers 2007, 88, 610-610.
May, J. P. ; Perrin, D. M. ; Fournier, P. Synthesis And Characterization Of Derivatives Of The Bicyclic Peptide Alpha-Amanitin. Biopolymers 2007, 88, 624-624.
May, J. P. ; Perrin, D. M. Tryptathionine Bridges In Peptide Synthesis. Biopolymers 2007, 88, 714-724.

2006

Thomas, J. M. ; Perrin, D. M. Active Site Labeling Of G8 In The Hairpin Ribozyme: Implications For Structure And Mechanism. Journal of the American Chemical Society 2006, 128, 16540-16545.
May, J. P. ; Perrin, D. M. A Mild Acidic Method For The Selective Deprotection Of N1-Trityl-3A-Hydroxypyrrolo[2,3-B]Indole Derivatives. In Understanding Biology Using Peptides; Blondelle, S. E. ; Understanding Biology Using Peptides; 2006; pp. 216-217.

2005

Ting, R. ; Adam, M. J. ; Ruth, T. J. ; Perrin, D. M. Arylfluoroborates And Alkylfluorosilicates As Potential Pet Imaging Agents: High-Yielding Aqueous Biomolecular F-18-Labeling. Journal of the American Chemical Society 2005, 127, 13094-13095.

2004

Ting, R. ; Lermer, L. ; Perrin, D. M. Triggering Dnazymes With Light: A Photoactive C8 Thioether-Linked Adenosine. Journal of the American Chemical Society 2004, 126, 12720-12721.
Ting, R. ; Lermer, L. ; Thomas, J. ; Roupioz, Y. ; Perrin, D. M. Selection And Characterization Of Dnazymes With Synthetically Appended Functionalities: A Case Of A Synthetic Rnasea Mimic. Pure and Applied Chemistry 2004, 76, 1571-1577.
Patel, A. ; Perrin, D. M. Efficient Synthesis Of Isotopically Pure Isotope-Coded Affinity Tagging Reagents. Bioconjugate Chemistry 2004, 15, 224-230.
Thomas, J. M. ; Ting, R. ; Perrin, D. M. High Affinity Dnazyme-Based Ligands For Transition Metal Cations - A Prototype Sensor For Hg2+. Organic & Biomolecular Chemistry 2004, 2, 307-312.
May, J. P. ; Ting, R. ; Lermer, L. ; Thomas, J. M. ; Roupioz, Y. ; Perrin, D. M. Covalent Schiff Base Catalysis And Turnover By A Dnazyme: A M2+ Independent Ap-Endonuclease Mimic. Journal of the American Chemical Society 2004, 126, 4145-4156.

2002

Lermer, L. ; Roupioz, Y. ; Ting, R. ; Perrin, D. M. Toward An Rnasea Mimic: A Dnazyme With Imidazoles And Cationic Amines. Journal of the American Chemical Society 2002, 124, 9960-9961.

2001

Chen, C. H. B. ; Milne, L. ; Landgraf, R. ; Perrin, D. M. ; Sigman, D. S. Artificial Nucleases. Chembiochem 2001, 2, 735-740.
Perrin, D. M. ; Garestier, T. ; Helene, C. Bridging The Gap Between Proteins And Nucleic Acids: A Metal-Independent Rnasea Mimic With Two Protein-Like Functionalities. Journal of the American Chemical Society 2001, 123, 1556-1563.