Imidazo[1,2- a ]pyrazine Derivatives as Dual A2A/A2B Adenosine Receptor Antagonists Enhancing Anti-PD-1 Antibody Therapy in Colorectal Cancer

Abstract Adenosine signaling through A2A and A2B adenosine receptors (ARs) suppresses antitumor immunity and promotes tumor progression, limiting immune checkpoint blockade in microsatellite-stable colorectal cancer (CRC). Here, we identified imidazo[1,2-a]pyrazine-urea derivatives as a new chemotype of dual hA2A/hA2B AR antagonists. SAR studies revealed that 3-iodination of the core scaffold enhanced receptor affinity and functional antagonism, with 5p emerging as a representative lead. MD simulations showed that 5p can be accommodated in the orthosteric pockets of both AR subtypes through distinct binding modes, with the 3-iodo substituent occupying adjacent subpockets. Representative compounds inhibited adenosine-induced CREB phosphorylation, restored Th1 cytokine production, and increased CD4+ and CD8+ T cell infiltration. In CD73-high CRC models, 5p suppressed tumor growth and potentiated anti-PD-1 efficacy. These findings support dual A2A/A2B AR antagonism as a strategy to reprogram the adenosine-rich tumor microenvironment and improve CRC immunotherapy.

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Publication Details

Journal
Journal of Medicinal Chemistry
Published
2026-10-22
DOI
https://doi.org/10.1021/acs.jmedchem.6c02638
Primary Topic
Adenosine and Purinergic Signaling
Type
article
Field-Weighted Citation Impact
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article

Imidazo[1,2- a ]pyrazine Derivatives as Dual A2A/A2B Adenosine Receptor Antagonists Enhancing Anti-PD-1 Antibody Therapy in Colorectal Cancer

Jiyoung Choi, Jiyeong Jung, Inah Hwang, Jinha Yu et al.
Journal of Medicinal Chemistry
Adenosine and Purinergic Signaling
article

Imidazo[1,2- a ]pyrazine Derivatives as Dual A2A/A2B Adenosine Receptor Antagonists Enhancing Anti-PD-1 Antibody Therapy in Colorectal Cancer

Jiyoung Choi, Jiyeong Jung, Inah Hwang, Jinha Yu, Jun Chang, Serin Lee, Yumi Heo, Chaeyeon Kim, Heonjoo Jeon
article en

Abstract

Abstract Adenosine signaling through A2A and A2B adenosine receptors (ARs) suppresses antitumor immunity and promotes tumor progression, limiting immune checkpoint blockade in microsatellite-stable colorectal cancer (CRC). Here, we identified imidazo[1,2-a]pyrazine-urea derivatives as a new chemotype of dual hA2A/hA2B AR antagonists. SAR studies revealed that 3-iodination of the core scaffold enhanced receptor affinity and functional antagonism, with 5p emerging as a representative lead. MD simulations showed that 5p can be accommodated in the orthosteric pockets of both AR subtypes through distinct binding modes, with the 3-iodo substituent occupying adjacent subpockets. Representative compounds inhibited adenosine-induced CREB phosphorylation, restored Th1 cytokine production, and increased CD4+ and CD8+ T cell infiltration. In CD73-high CRC models, 5p suppressed tumor growth and potentiated anti-PD-1 efficacy. These findings support dual A2A/A2B AR antagonism as a strategy to reprogram the adenosine-rich tumor microenvironment and improve CRC immunotherapy.

Journal of Medicinal Chemistry
Ewha Womans University (KR)
Openalex Percentile: Top 16%
Adenosine and Purinergic Signaling
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