Perrin Group 2014


Email: dperrin@chem.ubc.ca
Office Room Number: A343
Office Phone Number: 604-822-0567
Lab Phone Number: 604-822-6782


Summer barbeque 2014
Summer barbeque 2014
Christmas Dinner 2013
Christmas Dinner 2013


(2014 Current graduate members: Antoine Blanc, Erkai Liu, Yajun Wang, Jerome Lozada, kaveh matinkhoo, Emily Miller, Alla Pryyma)




List of Publications

2015

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.

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.

2014


Largy, E. ; Liu, W. ; Hasan, A. ; Perrin, D. M. A Pyrimidopyrimidine Janus-At Nucleoside With Improved Base-Pairing Properties To Both A And T Within A Dna Duplex: The Stabilizing Effect Of A Second Endocyclic Ring Nitrogen}. Chemistry 2014, 20, 1495–1499.

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. ; Radtke, M. A. ; Wong, M. Q. ; Lin, K. S. ; Yapp, D. T. ; Perrin, D. M. Dual Mode Fluorescent (18)F-Pet Tracers: Efficient Modular Synthesis Of Rhodamine-[Crgd]2-[(18)F]-Organotrifluoroborate, Rapid, And High Yielding One-Step (18)F-Labeling At High Specific Activity, And Correlated In Vivo Pet Imagi. Bioconjug. Chem. 2014, 25, 1951–1962.

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

Li, Y. ; Schaffer, P. ; Perrin, D. M. Dual isotope labeling of oligonucleotides with aryltrifluoroborate via copper(I) catalyzed cycloaddition for PET imaging. Bioorg Med. Chem. Lett. 2013 23: 6313-6316.

Li, Y. ; Liu, Z. ; Wong, M. Q. ; Lin, K-S. ; Yapp, D. ; Perrin, D. M. One-Step 18F-Labeling of Dimeric CycloRGD at High Specific Activity for Functional PET Imaging of Tumors in Mice. Nucl. Med. and Biol. 2013 40: 959-966.

Largy, E. ; Liu, W. ; Hasan, A. ; Perrin, D. M. Base-Pairing Behavior of a Carbacyclic Janus-AT Nucleoside Analogue Capable of Recognizing A and T within a DNA Duplex, ChemBioChem. 2013 14: 2199-2208.

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. and Biol. 2013 40: 841-849.

Hollenstein, M. ; Hipolito, C. J. ; Lam, C. H. ; Perrin, D. M. Towards the Combinatorial Selection of Sequence Specific RNaseA Mimics, ACS Combinatorial Science 2013 15:174-182.

Li, Y. ; Guo, J. ; Tang, S. ; Lang, L. ; Chen, X. ; Perrin, D. M. One-step and One-Pot-Two-Step Radiosynthesis of Cyclo-RGD-18F-Aryltrifluoroborate Conjugates for Functional Imaging, American Journal of Nuclear Medicine and Molecular Imaging 2013 3:44-56. Liu, Z. ; Li, Y. ; Lozada, J. ; Schaffer, P. ; Ruth, T. J. ; Adam, M. J. ; Perrin, D. M. Stoichiometric Leverage: Rapid [18F]-Aryltrifluoroborate Radiosynthesis at Exceptionally High Specific Activity For Click Conjugation. Angewandte Chemie 2013 52: 2304-7.

Li, Y. ; Liu, Z. ; Pourghiasian, M. ; Lin, K-S. ; Schaffer, P. ; Bénard, F. ; Perrin, D. M. , Alkyne-18F-ArBF3 for One-Pot Click 18F-Labeling of Bombesin for in vivo PET Imaging of Tumors Expressing the GRP-Receptor, American Journal of Nuclear Medicine and Molecular Imaging, 2013 3:57-70.

2012

Liu, Z. ; Li, Y. ; Lozada, 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. J. Labeled Compounds and Radiopharmaceuticals 2012 14: 491-97.

Zhao, L. ; May, J. P. ; Huang, J. ; Perrin, D. M. Stereoselective synthesis of Brevianamide E, Org. Lett. 2012 14: 90-93.

2011

Li, Y. ; Ting, R. ; Curtis W. Harwig, Bellac, C. L. ; Lange, P. F. ; Auf dem keller, U. ;, 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 Reversible MMPI, for in vivo PET Imaging of Cancer Associated Matrix Metalloproteases, MedChemComm 2011 2: 942-6.

Lam, C. H. ; Hipolito, C. J. ; Hollenstein, M. ; Perrin, D. M. A divalent metal-dependent self-cleaving DNAzyme with a tyrosine-like side chain. Org. Biomol. Chem. 2011 9: 6949-54.

Perrin, D. M. Life- Like but Not Living: Modified Nucleic Acids for Binding and Catalysis, (Invited Review), Comprehensive Polymer Science 2012 (In press)

Hipolito, C. J. ; Hollenstein, M. ; Lam, C. H. ; Perrin, D. M. Protein-Inspired Modified DNAzymes: Dramatic Effects of shortening side-chain length of 8-imidazolyl modified deoxyadenosines in selecting RNaseA Mimicking DNAzymes, Org. Biomol. Chem 2011 9: 2266-2273.

2010

Perrin, D. M. ; May, J. P. Internal Savige-Fontana Tryptathionylation In The Synthesis Of Bicyclic Peptide Toxins And An Unexpected Chemical Entree From Hpi-Containing Phakellistatin/omphalotin-Like Macrolactams. Journal of the American Chemical Society, 2010; p. ORGN-476.

Lam, C. H. ; Perrin, D. M. 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.

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. ; Bénard, 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. Journal of the American Chemical Society, 2010; p. BIOT-303.

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. Journal of the American Chemical Society, 2010; p. ORGN-430.

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.

May, J. P. ; Perrin, D. M. 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.

May, J. P. ; Fournier, P. ; Patrick, B. O. ; Perrin, D. M. Synthesis, Characterisation, And In Vitro Evaluation Of Pro(2)-Ile(3)-S-Deoxo-Amaninamide And Pro(2)-D-Allo-Ile(3)-S-Deoxo-Amaninamide: Implications For Structure-Activity Relationships In Amanitin Conformation And Toxicity. Chemistry-a European Journal 2008, 14, 3410-3417.

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 Society2008, 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.

Harwig, C. W. ; Ting, R. ; Adam, M. J. ; Ruth, T. J. ; Perrin, D. M. Synthesis And Characterization Of 2,6-Difluoro-4-Carboxyphenylboronic Acid And A Biotin Derivative Thereof As Captors Of Anionic Aqueous [F-18]-Fluoride For The Preparation Of [F-18/f-19]-Labeled Aryltrifluoroborates With High Kinetic Stability. Tetrahedron Letters 2008, 49, 3152-3156.

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.

Ting, R. ; Thomas, J. M. ; Perrin, D. M. 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.

May, J. P. ; Perrin, D. M. Diastereoselectivity In The Synthesis Of Syn-Cis-3A-Hydroxypyrrolo[2,3-B]Indoline N-A-Methyl-Dipeptide Methyl Esters. Biopolymers 2007, 88, 622-622.

May, J. P. ; Perrin, D. M. The Internal Savige-Fontana Reaction: Specific Intra-Annular Crosslinking Of Tryptophan To Cysteine In The Synthesis Of Amatoxins And Phallotoxins. Biopolymers 2007, 88, 618-618.

Dietrich, D. ; Perrin, D. M. Preparation Of Photocaged Derivatives Of Alpha-Amanitin. Biopolymers 2007, 88, 610-610.

Perrin, D. M. ; May, J. P. Revisting The Savige Fontana Reaction: Internal Creation Of Tryptathionine Afford A Link Between Two Disparate Classes Of Peptide Natural Products. Biopolymers 2007, 88, 514-514.

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. ; Patrick, B. O. ; Perrin, D. M. Diastereoselectivity In The Synthesis Of Syn-Cis-3A-Hydroxypyrrolo[2,3-B] Indoline N-A'-Methyl-Dipeptide Methyl Esters. Synlett 2006, 3403-3406.

May, J. P. ; Perrin, D. M. A Mild Acidic Method For The Selective Deprotection Of N1-Trityl-3A-Hydroxypyrrolo[2,3-B]Indole Derivatives. InUnderstanding Biology Using Peptides; Blondelle, S. E. ; Understanding Biology Using Peptides; 2006; pp. 216-217.

2005

May, J. P. ; Fournier, P. ; Pellicelli, J. ; Patrick, B. O. ; Perrin, D. M. High Yielding Synthesis Of 3A-Hydroxypyrrolo[2,3-B]Indoline Dipeptide Methyl Esters: Synthons For Expedient Introduction Of The Hydroxypyrroloindoline Moiety Into Larger Peptide-Based Natural Products And For The Creation Of Tryptathionine Bridges. Journal of Organic Chemistry 2005, 70, 8424-8430.

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.

Ting, R. ; Thomas, J. M. ; Lermer, L. ; Perrin, D. M. Substrate Specificity And Kinetic Framework Of A Dnazyme With An Expanded Chemical Repertoire: A Putative Rnasea Mimic That Catalyzes Rna Hydrolysis Independent Of A Divalent Metal Cation. Nucleic Acids Research 2004, 32, 6660-6672.

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.

Lermer, L. ; Hobbs, J. ; Perrin, D. M. Incorporation Of 8-Histaminyldeoxyadenosine [8-(2-(4-Imidazolyl)Ethylamino)-2 '-Deoxyriboadenosine] Into Oligodeoxyribonucleotides By Solid Phase Phosphoramidite Coupling. Nucleosides Nucleotides & Nucleic Acids2002, 21, 651-664.

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.