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Scaling Amatoxin Synthesis with an Improved Route to (2S,3R,4R)-Dihydroxyisoleucine Exemplified by a Toxic, Clickable α-Amanitin Analogue

Autor: David M. Perrin, Kaveh Matinkhoo, Chido M. Hambira, Brian O. Patrick, Alla Pryyma

Publikováno v: The Journal of Organic Chemistry. 86:5362-5370

Here we report a scalable synthesis of the key amino acid residue, (2S,3R,4R)-4,5-dihydroxyisoleucine (DHIle) in α-amanitin, that in turn enables the scalable synthesis of an equipotent analogue, Asn(N-ethylazide)-S,6'-dideoxy-α-amanitin, suitable

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::de961133eb8b13fe7eef932da54baecb
https://doi.org/10.1021/acs.joc.0c03022

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Rationally Designed Amanitins Achieve Enhanced Cytotoxicity

Autor: Mihajlo Todorovic, Paul Rivollier, Antonio A. W. L. Wong, Zhou Wang, Alla Pryyma, Tuan Trung Nguyen, Kayla C. Newell, Juliette Froelich, David M. Perrin

Publikováno v: Journal of medicinal chemistry. 65(15)

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 cyto

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::49543a0f84695a59e77bf9210066ab09
https://pubmed.ncbi.nlm.nih.gov/35696491

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Synthesis and evaluation of '

Autor: Kaveh, Matinkhoo, Alla, Pryyma, Antonio A W L, Wong, David M, Perrin

Publikováno v: Chemical communications (Cambridge, England). 57(75)

Amanitin is used extensively as a research tool to inhibit RNA Pol II thereby implicating its role in mRNA transcription. Recently, amanitin has gained traction as a toxic payload for targeted therapy. Here we report the first-ever photocaged amaniti

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=pmid________::a5c74f72efb965a0b652db46395f3d48
https://pubmed.ncbi.nlm.nih.gov/34477193

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One-Step 18F-Labeling and Preclinical Evaluation of Prostate-Specific Membrane Antigen Trifluoroborate Probes for Cancer Imaging

Autor: Jinhe Pan, Zhibo Liu, Áron Roxin, Helen Merkens, Hsiou-Ting Kuo, Chengcheng Zhang, Francois Benard, Alla Pryyma, Kuo-Shyan Lin, Mathieu L. Lepage, David M. Perrin, Zhengxing Zhang

Publikováno v: Journal of Nuclear Medicine. 60:1160-1166

After the identification of the high-affinity glutamate-ureido scaffold, the design of several potent 18F- and 68Ga-labeled tracers has allowed spectacular progress in imaging recurrent prostate cancer by targeting the prostate-specific membrane anti

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::d6eea4853aeae3edb629a6d180d67db5
https://doi.org/10.2967/jnumed.118.216598

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Meeting key synthetic challenges in amanitin synthesis with a new cytotoxic analog: 5'-hydroxy-6'-deoxy-amanitin

Autor: Antonio A. W. L. Wong, David M. Perrin, Alla Pryyma, Kaveh Matinkhoo

Publikováno v: Chemical Science

Appreciating the need to access synthetic analogs of amanitin, here we report the synthesis of 5′-hydroxy-6′-deoxy-amanitin, a novel, rationally-designed bioactive analog and constitutional isomer of α-amanitin, that is anticipated to be used as

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::b60896f79ed1c390436c9396265cce77
https://pubmed.ncbi.nlm.nih.gov/34094418

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Scaling Amatoxin Synthesis with an Improved Route to (2

Autor: Chido M, Hambira, Kaveh, Matinkhoo, Alla, Pryyma, Brian O, Patrick, David M, Perrin

Publikováno v: The Journal of organic chemistry. 86(7)

Here we report a scalable synthesis of the key amino acid residue, (2

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=pmid________::5ad10886c2e30edc6cc8d771286c5f16
https://pubmed.ncbi.nlm.nih.gov/33710901

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Synthesis of the Death-Cap Mushroom Toxin α-Amanitin

Autor: Mihajlo Todorovic, Brian O. Patrick, Alla Pryyma, Kaveh Matinkhoo, David M. Perrin

Publikováno v: Journal of the American Chemical Society. 140:6513-6517

α-Amanitin is an extremely toxic bicyclic octapeptide isolated from the death-cap mushroom, Amanita phalloides. As a potent inhibitor of RNA polymerase II, α-amanitin is toxic to eukaryotic cells. Recent interest in α-amanitin arises from its prom

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::eeb5a291832ff26810ff0e66c42cfa83
https://doi.org/10.1021/jacs.7b12698

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Synthesis and Activation of Bench-Stable 3a-Fluoropyrroloindolines as Latent Electrophiles for the Synthesis of C-2-Thiol-Substituted Tryptophans and C-3a-Substituted Pyrroloindolines

Autor: David M. Perrin, Yonnie Wai, Yong Jia Bu, Alla Pryyma, Brian O. Patrick

Publikováno v: Organic letters. 21(20)

Indole dearomatization of tryptophan represents a key approach in the synthesis of indole containing alkaloids. Although the reactivity of C-3a-bromo-, 3a-iodo-, and 3a-chloropyrroloindolines has been explored, the utility and reactivity of C-3a-fluo

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::c5b57643cceeec9e93430c9758162d9b
https://pubmed.ncbi.nlm.nih.gov/31596101

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One-Step

Autor: Hsiou-Ting, Kuo, Mathieu L, Lepage, Kuo-Shyan, Lin, Jinhe, Pan, Zhengxing, Zhang, Zhibo, Liu, Alla, Pryyma, Chengcheng, Zhang, Helen, Merkens, Aron, Roxin, David M, Perrin, François, Bénard

Publikováno v: Journal of Nuclear Medicine

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=pmid________::2625bce34398598bb409e379ad2cbf78
https://pubmed.ncbi.nlm.nih.gov/30737299

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