{"doi":"10.1021/cbmi.5c00205","title":"A New Class of Anionic Near-Infrared Fluorescent Dyes with 1,6-Diheterophenalene-2,5-dione End Groups","abstract":"We describe the synthesis and evaluation of oxonol-based near-infrared (NIR) dyes designed for in vivo optical imaging applications. These small-molecule anionic dyes, dubbed FROGs (Fiercely Radiant Oxonol Green), exhibit strong NIR absorption and emission, high molar absorptivity, and good photostability. In vitro studies revealed distinct cellular uptake profiles: whereas compound FROG-1 displayed minimal cellular internalization, FROG-2 showed robust accumulation in cancer cells. Fluorescence lifetime imaging microscopy (FLIM) further revealed that FROG-2 produced a uniform and prolonged lifetime signal within cancer cells, indicative of stable intracellular localization. Both representative compounds were administered to nude mice and monitored using multispectral fluorescence imaging across a broadband excitation/emission channel combinations between 500 and 840 nm. Principal component analysis of the imaging data revealed distinct temporal and spatial distribution patterns: FROG-1 demonstrated renal clearance with minimal off-target accumulation, while FROG-2 showed mixed renal and hepatic clearance and spectral heterogeneity at early time points, suggesting differential stability or interaction with tissue microenvironments. Ex vivo organ imaging at 24 h confirmed these clearance routes. These findings highlight the potential of tailored oxonol dyes as versatile NIR probes and provide insight into the structure-biodistribution relationship critical for biomedical imaging probe development.","journal":"Chemical & Biomedical Imaging","year":2025,"id":537614,"datarank":0.10397207708399181,"base_score":0.6931471805599453,"endowment":0.6931471805599453,"self_citation_contribution":0.10397207708399181,"citation_network_contribution":0.0,"self_endowment_contribution":0.10397207708399181,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":1,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9547,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2025-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":245687,"name":"Rui Tang","orcid":"0000-0002-2734-1003","position":1,"is_corresponding":false},{"id":289137,"name":"Megan S. Michie","orcid":"0000-0001-8749-4063","position":2,"is_corresponding":false},{"id":716263,"name":"Christina Lin","orcid":null,"position":3,"is_corresponding":false},{"id":374987,"name":"Mikhail Y. Berezin","orcid":"0000-0002-2670-2487","position":4,"is_corresponding":false},{"id":1423401,"name":"Vladimir B. Birman","orcid":"0000-0003-0299-358X","position":5,"is_corresponding":false},{"id":1423844,"name":"Isaac Fuentes","orcid":null,"position":0,"is_corresponding":true}],"reference_count":21,"raw_metadata":{"citation_network_status":"fetched"},"created_at":"2026-07-19T02:52:12.997494Z","pmid":"42222561","pmcid":null,"fwci":null,"citation_percentile":null,"influential_citations":0,"oa_status":null,"license":null,"views":0,"total_file_size_bytes":0,"version_count":0,"fair_f":null,"fair_a":null,"fair_i":null,"fair_r":null,"fair_zscore":null,"fair_rationale":null,"fair_model":null,"fair_agent_version":null,"fair_fulltext_source":null,"fair_has_llm":null,"fair_computed_at":null,"clinical_trials":[],"software_tools":[],"db_accessions":[],"linked_datasets":[],"topics":[]}