Near-infrared cyanine dyes and their conjugates

Novel cyanine dyes with low albumin binding affinity and targeted conjugates address solubility and specificity issues in near-infrared imaging, enhancing diagnostic accuracy for tumors and surgical applications.

JP7747660B2Active Publication Date: 2025-10-01BRACCO IMAGING SPA
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Patent Information

Application Number
JP2022567490
Authority / Receiving Office
JP · JP
Patent Type
Patents
Current Assignee / Owner
Priority Date
2020-06-23
Filing Date
2021-06-22
Publication Date
2025-10-01
Estimated Expiration
2041-06-22

AI Technical Summary

Technical Problem

Existing near-infrared dyes for biomedical imaging face challenges with optimal solubility, low aggregation in aqueous media, high fluorescence efficiency, and suboptimal biological properties, particularly when conjugated to biomolecules targeting pathological tissues like tumors, leading to nonspecific accumulation and reduced diagnostic efficacy.

Method used

Development of novel cyanine dyes with low binding affinity for human albumin, allowing for efficient extravasation and distribution, and their conjugates with targeting moieties for specific tissue binding, enhancing imaging specificity and sensitivity.

Benefits of technology

The novel cyanine dyes provide improved solubility and fluorescence efficiency, reducing plasma sequestration and enabling highly specific and sensitive contrast agents for molecular imaging, particularly in tumor detection and surgical guidance.

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Abstract

The present invention relates to the field of optical imaging. More specifically, the present invention relates to compounds of the cyanine family with near-infrared emission and their conjugates with biological ligands, characterized by improved physicochemical and biological properties. The present invention also relates to the use of these compounds as optical diagnostic agents in the imaging or therapy of solid tumors, their preparation methods, and compositions containing them. The compound has formula (I), where X is a direct bond or -O-; Y is a group selected from linear or branched C-C alkyl, C-C cycloalkyl, and heterocyclyl substituted by at least two hydroxyl groups; R and R are each independently linear or branched C-C alkyl substituted by a group selected from -SOH, -COOH, -CONH, and -COO-C-C alkyl; and R is hydrogen, -SOH, or linear or branched C-C alkyl substituted by -COOH or -CONH-Y, where Y is a group selected from linear or branched C-C alkyl, C-C cycloalkyl, and heterocyclyl substituted by at least two hydroxyl groups. JPEG2023530575000042.jpg72166
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