David Perrin
Profile
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]
Winter Holiday 2007
Contact
Real name:
Office Room Number(s):
A343
Office Phone Number:
604-822-0567
Office Hours:
Wednesday Afternoons
Publications
2015
Synthesis Of A Cytotoxic Amanitin For Biorthogonal Conjugation}. Chembiochem 2015, 16, 1420–1425.
(18)F-Ambf3-Mj9: A Novel Radiofluorinated Bombesin Derivative For Prostate Cancer Imaging}. Bioorg. Med. Chem. 2015, 23, 1500–1506.
From Minutes To Years: Predicting Organotrifluoroborate Solvolysis Rates}. Chemistry 2015, 21, 3924–3928.
A Method For Selecting Modified Dnazymes Without The Use Of Modified Dna As A Template In Pcr. Chem. Commun. (Camb.) 2015, 51, 1360–1362.
Synthesis And Enzymatic Incorporation Of Modified Deoxyuridine Triphosphates}. Molecules 2015, 20, 13591–13602.
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.
Radiosynthesis And Evaluation Of 18F-Ambf3-Toc For Imaging Somatostatin Receptor With Positron Emission Tomography. Journal of Nuclear Medicine 2015, 56, 1136.
18F-Ambf3-Phosphonium Cations For Myocardial Perfusion Imaging With Positron Emission Tomography. Journal of Nuclear Medicine 2015, 56, 1081.
Designing Kinetically Stable Aryltrifluoroborates As 18F-Capture Agents For Pet Imaging. Journal of Physical Organic Chemistry 2015, 28, 210–214.
2014
An Organotrifluoroborate For Broadly Applicable One-Step 18F-Labeling. Angewandte Chemie International Edition 2014, 53, 11876–11880.
Base-Promoted Protodeboronation Of 2,6-Disubstituted Arylboronic Acids}. J. Org. Chem. 2014, 79, 5365–5368.
Preclinical Evaluation Of A High-Affinity 18F-Trifluoroborate Octreotate Derivative For Somatostatin Receptor Imaging}. J. Nucl. Med. 2014, 55, 1499–1505.
2013
One Step F-18-Labeling Of Complex Peptides For Functional Pet Imaging. BIOPOLYMERS 2013, 100, 242.
Synthesis Of ``smart Drug'': Amanitin Conjugates. BIOPOLYMERS 2013, 100, 263.
Synthesis Of A Fluorescent And 18E-Labeled Psma Inhibitor For Targeted Imaging Of Prostate Cancer. BIOPOLYMERS 2013, 100, 293-294.
Stoichiometric Leverage: Rapid 18F-Aryltrifluoroborate Radiosynthesis At High Specific Activity For Click Conjugation. Angewandte Chemie International Edition 2013, 52, 2303–2307.
Novel 18F-Radiolabeling Of Rgd At Super High Specific Activity By Isotope Exchange. BIOPOLYMERS 2013, 100, 295.
Toward The Combinatorial Selection Of Chemically Modified Dnazyme Rnase A Mimics Active Against All-Rna Substrates. ACS Combinatorial Science 2013, 15, 174-182.
Single Step 18F-Labeling Of Dimeric Cyclorgd For Functional Pet Imaging Of Tumors In Mice}. Nucl. Med. Biol. 2013, 40, 959–966.
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.
Dual Isotope Labeling: Conjugation Of 32P-Oligonucleotides With 18F-Aryltrifluoroborate Via Copper(I) Catalyzed Cycloaddition}. Bioorg. Med. Chem. Lett. 2013, 23, 6313–6316.
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.
(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.
Novel F-18-Radiolabeling Of Rgd At Super High Specific Activity By Isotope Exchange. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS 2013, 56, S167.
``kit'' F-18-Radiolabeling Based On B-F Bond Formation. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS 2013, 56, S166.
2012
Stereoselective Synthesis Of Brevianamide E. Org. Lett. 2012, 14, 90-93.
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.
Enhancing Catalytic Activity Of Nucleic Acids By Making Them More Protein Like. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY 2012, 243.
Rapid, One Step Aqueous 18F-Labeling Of Peptides For Pet Imaging. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY 2012, 243.
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.
2011
A Divalent Metal-Dependent Self-Cleaving Dnazyme With A Tyrosine Side Chain. Org. Biomol. Chem. 2011, 9, 6949-6954.
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
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.
Internal Savige-Fontana Tryptathionylation In The Synthesis Of Bicyclic Peptide Toxins And An Unexpected Chemical Entree From Hpi-Containing Phakellistatin/omphalotin-Like Macrolactams. In; American Chemical Society, 2010; p. ORGN-476.
Introduction Of Guanidinium-Modified Deoxyuridine Into The Substrate Binding Regions Of Dnazyme 10-23 To Enhance Target Affinity: Implications For Dnazyme Design. Bioorganic & Medicinal Chemistry Letters 2010, 20, 5119 - 5122.
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.
Synthetic Rna-Cleaving Dnazymes With Three Protein Side Chains: Amines, Imidazoles, And Guanidines. In; American Chemical Society, 2010; p. BIOT-303.
2009
Substrate Degradomics And Activity Imaging Of Matrix Metalloproteinases In Breast Carcinogenesis. Clinical & Experimental Metastasis 2009, 26, 866-866.
Probing General Acid Catalysis In The Hammerhead Ribozyme. Journal of the American Chemical Society 2009, 131, 1135-1143.
A Dnazyme With Three Protein-Like Functional Groups: Enhancing Catalytic Efficiency Of M2+-Independent Rna Cleavage. Chembiochem 2009, 10, 1988-1992.
Hydrolytic Stability Of Nitrogenous-Heteroaryltrifluoroborates Under Aqueous Conditions At Near Neutral Ph. Journal of Fluorine Chemistry 2009, 130, 377-382.
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.
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
Probing General Base Catalysis In The Hammerhead Ribozyme. Journal of the American Chemical Society 2008, 130, 15467-15475.
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.
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.
A Highly Selective Dnazyme Sensor For Mercuric Ions. Angewandte Chemie-International Edition 2008, 47, 4346-4350.
Intraannular Savige-Fontana Reaction: One-Step Conversion Of One Class Of Monocyclic Peptides Into Another Class Of Bicyclic Peptides. Chemistry-a European Journal 2008, 14, 3404-3409.
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.
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-+.
Synthesis And Enzymatic Incorporation Of Modified Deoxyadenosine Triphosphates. European Journal of Organic Chemistry 2008, 4915-4923.
2007
Janus-At Bases: Synthesis, Self-Assembly, And Solid State Structures. Journal of Organic Chemistry 2007, 72, 466-475.
Kinetic Characterization Of A Cis- And Trans-Acting M2+-Independent Dnazyme That Depends On Synthetic Rnasea-Like Functionality - Burst-Phase Kinetics From The Coalescence Of Two Active Dnazyme Folds. Canadian Journal of Chemistry-Revue Canadienne De Chimie 2007, 85, 313-329.
Diastereoselectivity In The Synthesis Of Syn-Cis-3A-Hydroxypyrrolo[2,3-B]Indoline N-A-Methyl-Dipeptide Methyl Esters. Biopolymers 2007, 88, 622-622.
Preparation Of Photocaged Derivatives Of Alpha-Amanitin. Biopolymers 2007, 88, 610-610.
Synthesis And Characterization Of Derivatives Of The Bicyclic Peptide Alpha-Amanitin. Biopolymers 2007, 88, 624-624.
Tryptathionine Bridges In Peptide Synthesis. Biopolymers 2007, 88, 714-724.
2006
A Mild Acidic Method For The Selective Deprotection Of N1-Trityl-3A-Hydroxypyrrolo[2,3-B]Indole Derivatives. In Understanding Biology Using Peptides; ; Understanding Biology Using Peptides; 2006; pp. 216-217.
Active Site Labeling Of G8 In The Hairpin Ribozyme: Implications For Structure And Mechanism. Journal of the American Chemical Society 2006, 128, 16540-16545.
2005
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
Triggering Dnazymes With Light: A Photoactive C8 Thioether-Linked Adenosine. Journal of the American Chemical Society 2004, 126, 12720-12721.
Selection And Characterization Of Dnazymes With Synthetically Appended Functionalities: A Case Of A Synthetic Rnasea Mimic. Pure and Applied Chemistry 2004, 76, 1571-1577.
Efficient Synthesis Of Isotopically Pure Isotope-Coded Affinity Tagging Reagents. Bioconjugate Chemistry 2004, 15, 224-230.
High Affinity Dnazyme-Based Ligands For Transition Metal Cations - A Prototype Sensor For Hg2+. Organic & Biomolecular Chemistry 2004, 2, 307-312.
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
Toward An Rnasea Mimic: A Dnazyme With Imidazoles And Cationic Amines. Journal of the American Chemical Society 2002, 124, 9960-9961.
Incorporation Of 8-Histaminyldeoxyadenosine [8-(2-(4-Imidazolyl)Ethylamino)-2 ’-Deoxyriboadenosine] Into Oligodeoxyribonucleotides By Solid Phase Phosphoramidite Coupling. Nucleosides Nucleotides & Nucleic Acids 2002, 21, 651-664.
2001
Artificial Nucleases. Chembiochem 2001, 2, 735-740.
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.