{"doi":"10.1002/chir.23236","title":"Development of near‐infrared firefly luciferin analogue reacted with wild‐type and mutant luciferases","abstract":"<jats:title>Abstract</jats:title><jats:p>Interestingly, only the <jats:italic>D</jats:italic>‐form of firefly luciferin produces light by luciferin–luciferase (L–L) reaction. Certain firefly luciferin analogues with modified structures maintain bioluminescence (BL) activity; however, all <jats:italic>L</jats:italic>‐form luciferin analogues show no BL activity. To this date, our group has developed luciferin analogues with moderate BL activity that produce light of various wavelengths. For in vivo bioluminescence imaging, one of the important factors for detection sensitivity is tissue permeability of the number of photons emitted by L–L reaction, and the wavelengths of light in the near‐infrared (NIR) range (700–900 nm) are most appropriate for the purpose. Some NIR luciferin analogues by us had performance for in vivo experiments to make it possible to detect photons from deep target tissues in mice with high sensitivity, whereas only a few of them can produce NIR light by the L–L reactions with wild‐type luciferase and/or mutant luciferase. Based on the structure–activity relationships, we designed and synthesized here a luciferin analogue with the 5‐allyl‐6‐dimethylamino‐2‐naphthylethenyl moiety. This analogue exhibited NIR BL emissions with wild‐type luciferase (<jats:italic>λ</jats:italic><jats:sub>max</jats:sub> = 705 nm) and mutant luciferase AlaLuc (<jats:italic>λ</jats:italic><jats:sub>max</jats:sub> = 655 nm).</jats:p>","journal":"Chirality","year":2020,"id":21789,"datarank":0.6988874265336604,"base_score":2.8903717578961645,"endowment":2.8903717578961645,"self_citation_contribution":0.4335557636844247,"citation_network_contribution":0.26533166284923576,"self_endowment_contribution":0.4335557636844247,"citer_contribution":0.26533166284923576,"corpus_percentile":null,"corpus_rank":null,"citation_count":17,"citer_count":12,"citers_with_citation_signal":10,"citers_with_endowment":10,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":null,"is_data_producer":false,"deposit_databanks":null,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":null,"fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":139034,"name":"Ryohei Saito","orcid":null,"position":1,"is_corresponding":false},{"id":139035,"name":"Rika Obata","orcid":null,"position":2,"is_corresponding":false},{"id":139036,"name":"Satoshi Iwano","orcid":null,"position":3,"is_corresponding":false},{"id":139037,"name":"Kazuma Karube","orcid":null,"position":4,"is_corresponding":false},{"id":44850,"name":"Atsushi Miyawaki","orcid":"0000-0002-0671-4376","position":5,"is_corresponding":false},{"id":139040,"name":"Takashi Hirano","orcid":null,"position":6,"is_corresponding":false},{"id":139041,"name":"Shojiro A. Maki","orcid":"0000-0002-9741-0166","position":7,"is_corresponding":false},{"id":139033,"name":"Nobuo Kitada","orcid":null,"position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"base_score":2.8903717578961645,"endowment":2.8903717578961645,"datacite_reuse_total":0,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"32367573","pmcid":"PMC7383472","openalex_id":"https://openalex.org/W3021775193","authors":[],"funders":[{"funder_name":"Adaptable and Seamless Technology Transfer Program through Target-Driven R and D","grant_id":"AS2614119N","title":null},{"funder_name":"Research Corporation for Scientific Advancement","grant_id":"JP18K05075","title":null},{"funder_name":"Scientific Research on Innovative Areas \"Resonance Bio\"","grant_id":"JP15H05948","title":null},{"funder_name":"Scientific Research on Innovative Areas \"Soft Crystals\"","grant_id":"JP17H06371","title":null},{"funder_name":"Kurogane Kasei Co., Ltd.","grant_id":"","title":null},{"funder_name":"Kurogane Kasei Co., Ltd.","grant_id":"","title":null}],"total_grants":6,"fwci":1.0002,"citation_percentile":0.74481826,"influential_citations":1,"citation_trend":[{"year":2020,"count":4},{"year":2021,"count":4},{"year":2022,"count":2},{"year":2023,"count":2},{"year":2024,"count":3},{"year":2025,"count":1},{"year":2026,"count":1}],"oa_status":"hybrid","license":"cc-by","oa_locations":[{"url":"https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/chir.23236","host_type":"journal"},{"url":"https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/chir.23236","host_type":"HYBRID"},{"url":"https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/chir.23236","host_type":"publisher"},{"url":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchir.23236","host_type":"publisher"},{"url":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/chir.23236","host_type":"publisher"},{"url":"https://onlinelibrary.wiley.com/doi/full-xml/10.1002/chir.23236","host_type":"publisher"},{"url":"https://onlinelibrary.wiley.com/doi/am-pdf/10.1002%2Fchir.23236","host_type":"publisher"},{"url":"https://doi.org/10.1002/chir.23236","host_type":"journal"},{"url":"https://pubmed.ncbi.nlm.nih.gov/32367573","host_type":"repository"},{"url":"https://www.ncbi.nlm.nih.gov/pmc/articles/7383472","host_type":"repository"},{"url":"https://europepmc.org/articles/PMC7383472","host_type":"Europe_PMC"},{"url":"https://europepmc.org/articles/PMC7383472?pdf=render","host_type":"Europe_PMC"}],"fields_of_study":["bioluminescence and chemiluminescence research","Photoreceptor and optogenetics research","Biosensors and Analytical Detection","Medicine","Chemistry","Animals","Firefly Luciferin","Luciferases","Luminescent Measurements","Mice","Stereoisomerism","Structure-Activity Relationship"],"mesh_terms":["Animals","Luciferases","Luminescent Measurements","Stereoisomerism","Structure-Activity Relationship","Firefly Luciferin","Mice"],"keywords":["Luciferin","Luciferases","Luciferase","Bioluminescence","Chemistry","Mutant","Light emission","Photoprotein","In vivo","Biophysics","Bioluminescence imaging","Firefly protocol","Photochemistry","Biochemistry","Optics","Biology","Photinus Pyralis Luciferase","Luciferin-luciferase Reaction","Akaluc","Tokeoni","Luciferin Analogues","Mutant Luciferase","Near-infrared Bioluminescence"],"sdg_mappings":[],"linked_datasets":[],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-06-06T16:49:33.316275Z","pmid":null,"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":[]}