Juliette Froelich

University of British Columbia

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David M. Perrin

University of British Columbia

Mihajlo Todorovic

University of British Columbia

Pascale Roome

University of British Columbia

Naysilla Dayanara

University of British Columbia

Kayla C. Newell

University of British Columbia

Katherine Bessai

Chengcheng Zhang

State Key Laboratory of Food Science and Technology

Alla Pryyma

University of British Columbia

Zhou Wang

Sichuan University

Tuan Trung Nguyen

University of British Columbia

Cooperative Institutions

University of British Columbia

Vancouver Biotech (Canada)

University of British Columbia Hospital

BC Cancer Agency

Terry Fox Research Institute

Universidad Braulio Carrillo

Occupational Cancer Research Centre

Jiangnan University

Sichuan University

Spinal Cord Injury BC

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Rationally Designed Amanitins Achieve Enhanced Cytotoxicity

Journal of Medicinal Chemistry (2022)

Mihajlo Todorovic Paul Rivollier Antonio A. W. L. Wong Zhou Wang Alla Pryyma

For 70 years, α-amanitin, the most cytotoxic peptide in its class, has been without a synthetic rival; through synthesis, we address the structure–activity relationships to inform the design of new amatoxins and disclose analogues that are more cytotoxic than the natural product when evaluated on CHO, HEK293, and HeLa cells, whereas on liver-derived HepG2 cells, the same toxins show diminished cytotoxicity.

HeLa

Natural product

HEK 293 cells

Structure–activity relationship

10.1021/acs.jmedchem.1c02226

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Citations (7)

Chemoselective, Regioselective, and Positionally Selective Fluorogenic Stapling of Unprotected Peptides for Cellular Uptake and Direct Cell Imaging

Chemical Science (2024)

Naysilla Dayanara Juliette Froelich Pascale Roome David M. Perrin

A mild, rapid, highly selective fluorogenic peptide stapling method is presented resulting in bright green fluorescence. This enables direct assessment of cell uptake via confocal microscopy by virtue of the fluorescent staple itself.

10.1039/d4sc04839c

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5‐Hydroxypyrroloindoline Affords Tryptathionine and 2,2′‐bis‐Indole Peptide Staples: Application to Melanotan‐II

Chemistry - A European Journal (2024)

Mihajlo Todorovic Antoine Blanc Zhou Wang Jerome Lozada Juliette Froelich

With peptides increasingly favored as drugs, natural product motifs, namely the tryptathionine staple, found in amatoxins and phallotoxins, and the 2,2'-bis-indole found in staurosporine represent unexplored staples for unnatural peptide macrocycles. We disclose the efficient condensation of a 5-hydroxypyrroloindoline with either a cysteine-thiol or a tryptophan-indole to form a tryptathionine or 2-2'-bis-indole staple. Judicious use of protecting groups provides for chemoselective stapling using α-MSH, which provides a basis for investigating both chemoselectivity and affinity. Both classes of stapled peptides show nanomolar K

Chemoselectivity

Staurosporine

10.1002/chem.202304270

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Synthesis of Aza-Amanitins to Enhance Cytotoxicity for Targeted Cancer Therapeutics

Proceedings of the 35th European Peptide Symposium (2024)

Kayla C. Newell F. Cruz Custodinho Juliette Froelich Katherine Bessai Cassandra M. Sgarbi

10.17952/37eps.2024.p1084

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Author response for "Chemoselective, Regioselective, and Positionally Selective Fluorogenic Stapling of Unprotected Peptides for Cellular Uptake and Direct Cell Imaging"

Naysilla Dayanara Juliette Froelich Pascale Roome David M. Perrin

10.1039/d4sc04839c/v2/response1

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