Diverse reactivity of maleimides in polymer science and beyond DOI Creative Commons
Bruce E. Kirkpatrick, Kristi S. Anseth, Tayler S. Hebner

и другие.

Polymer International, Год журнала: 2024, Номер 74(4), С. 296 - 306

Опубликована: Ноя. 5, 2024

Abstract Maleimides are remarkably versatile functional groups, capable of participating in homo‐ and copolymerizations, Diels–Alder (photo)cycloadditions, Michael additions, other reactions. Their reactivity has afforded materials ranging from polyimides with high upper service temperatures to hydrogels for regenerative medicine applications. Moreover, maleimides have proven be an enabling chemistry pharmaceutical development bioconjugation via straightforward modification cysteine residues. To exert spatiotemporal control over reactions maleimides, multiple approaches been developed photocage nucleophiles, dienes, dipoles. Additionally, further substitution the maleimide alkene (e.g. monohalo‐, dihalo‐, thio‐, amino‐ methyl‐maleimides, among substituents) confers tunable dynamicity, as well responsive mechanical optical properties. In this mini‐review, we highlight diverse functionality underscoring their notable impact polymer science. This moiety related heterocycles will play important role future innovations chemistry, biomedical, research. © 2024 The Author(s). Polymer International published by John Wiley & Sons Ltd on behalf Society Chemical Industry.

Язык: Английский

Not So Bioorthogonal Chemistry DOI Creative Commons

Dominik Schauenburg,

Tanja Weil

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Фев. 28, 2025

The advent of bioorthogonal chemistry has transformed scientific research, offering a powerful tool for selective and noninvasive labeling (bio)molecules within complex biological environments. This innovative approach facilitated the study intricate cellular processes, protein dynamics, interactions. Nevertheless, number challenges remain to be addressed, including need improved reaction kinetics, enhanced biocompatibility, development more diverse orthogonal set reactions. While scientists continue search veritable solutions, remains transformative with vast potential advancing our understanding biology medicine. Perspective offers insights into reactions commonly classified as "bioorthogonal", which, however, may not always demonstrate desired selectivity regarding interactions between their components additives or catalysts used under conditions.

Язык: Английский

Процитировано

1

Regulating the Orientation of Homobivalent Small Binders Through 3d Domain-Swapping Design DOI

Shota Shiga,

Hideki Watanabe, Koki Makabe

и другие.

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

0

Development of ASGR-Mediated Hepatocyte-Targeting Cytotoxic Drug Conjugates with CTSB-Cleavable Linkers Incorporating Succinimide and Succinic Acid Monoamide DOI

Jingsheng Jiang,

S Jian,

Feifei Lin

и другие.

Journal of Medicinal Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 7, 2025

The ASGR-mediated endocytosis has been successfully applied to the hepatocyte-targeted delivery of therapeutic oligonucleotides via glycoconjugates. However, few studies have explored conjugated small molecules due challenge cleaving suitable linkers for release active molecules, which is especially different from GalNAc-ONs cleaved by deoxyribonuclease II in lysosome. In this study, GalNAc-MMAE conjugates linked CTSB-cleavable were designed and synthesized. A comprehensive approach revealed that endocytosed ASGR subsequently hydrolyzed CTSB, releasing MMAE. optimized conjugate with a succinic acid monoamide as fragment linker demonstrated favorable plasma stability, excellent biodistribution, significant antitumor activities vivo weight gain at effective dose an orthotopic hepatocellular carcinoma mouse model. This research provides strategy developing anti-HCC agents using GalNAc drug molecules.

Язык: Английский

Процитировано

0

Photocatalyzed elaboration of antibody-based bioconjugates DOI Creative Commons

Marine Le Stum,

Eugénie Romero,

Gary A. Molander

и другие.

Beilstein Journal of Organic Chemistry, Год журнала: 2025, Номер 21, С. 616 - 629

Опубликована: Март 18, 2025

Antibody–drug conjugates (ADCs) represent a promising class of targeted therapeutics, combining the specificity antibodies with potency cytotoxic drugs to enhance therapeutic efficacy while minimizing off-target effects. The development new chemical methods for bioconjugation is essential generate ADCs and optimize their stability, efficacy, safety. Traditional conjugation often face challenges related site-selectivity heterogeneous product mixtures, highlighting need develop new, innovative strategies. Photoredox chemistry emerges as powerful tool in this context, enabling precise, mild, selective modifications peptides proteins. By harnessing light drive transformations, photoredox techniques can facilitate synthesis antibody bioconjugates. This perspective will discuss empower applied functionalization.

Язык: Английский

Процитировано

0

Chemo-Click: Receptor-Controlled and Bioorthogonal Chemokine Ligation for Real-Time Imaging of Drug-Resistant Leukemic B Cells DOI Creative Commons
Marco Bertolini, Lorena Mendive‐Tapia, Utsa Karmakar

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(44), С. 30565 - 30572

Опубликована: Окт. 23, 2024

Drug resistance in B cell leukemia is characterized by the coexpression of CXCR5 and CXCR3 chemokine receptors, making it a valuable biomarker for patient stratification. Herein, we report novel platform activatable chemokines to selectively image drug-resistant leukemic cells first time. The C-terminal derivatization human CXCL13 CXCL10 with bioorthogonal tetrazine-BODIPY BCN groups retained binding internalization via their cognate receptors enabled rapid fluorescence labeling CXCR5+ CXCR3+ resistant cells─but not drug-susceptible cells─via intracellular ligation. This modular chemical approach offers versatile strategy real-time immunophenotyping populations distinct profiles will accelerate design new precision medicine tools advance personalized therapies blood tumors.

Язык: Английский

Процитировано

1

Diverse reactivity of maleimides in polymer science and beyond DOI Creative Commons
Bruce E. Kirkpatrick, Kristi S. Anseth, Tayler S. Hebner

и другие.

Polymer International, Год журнала: 2024, Номер 74(4), С. 296 - 306

Опубликована: Ноя. 5, 2024

Abstract Maleimides are remarkably versatile functional groups, capable of participating in homo‐ and copolymerizations, Diels–Alder (photo)cycloadditions, Michael additions, other reactions. Their reactivity has afforded materials ranging from polyimides with high upper service temperatures to hydrogels for regenerative medicine applications. Moreover, maleimides have proven be an enabling chemistry pharmaceutical development bioconjugation via straightforward modification cysteine residues. To exert spatiotemporal control over reactions maleimides, multiple approaches been developed photocage nucleophiles, dienes, dipoles. Additionally, further substitution the maleimide alkene (e.g. monohalo‐, dihalo‐, thio‐, amino‐ methyl‐maleimides, among substituents) confers tunable dynamicity, as well responsive mechanical optical properties. In this mini‐review, we highlight diverse functionality underscoring their notable impact polymer science. This moiety related heterocycles will play important role future innovations chemistry, biomedical, research. © 2024 The Author(s). Polymer International published by John Wiley & Sons Ltd on behalf Society Chemical Industry.

Язык: Английский

Процитировано

1