Meso-ester and carboxylic acid substituted BODIPYs with far-red and near-infrared emission for bioimaging applications

Handle URI:
http://hdl.handle.net/10754/563346
Title:
Meso-ester and carboxylic acid substituted BODIPYs with far-red and near-infrared emission for bioimaging applications
Authors:
Ni, Yong; Zeng, Lintao; Kang, Namyoung; Huang, Kuo-Wei ( 0000-0003-1900-2658 ) ; Wang, Liang; Zeng, Zebing; Chang, Young-Tae; Wu, Jishan
Abstract:
A series of meso-ester-substituted BODIPY derivatives 1-6 are synthesized and characterized. In particular, dyes functionalized with oligo(ethylene glycol) ether styryl or naphthalene vinylene groups at the α positions of the BODIPY core (3-6) become partially soluble in water, and their absorptions and emissions are located in the far-red or near-infrared region. Three synthetic approaches are attempted to access the meso-carboxylic acid (COOH)-substituted BODIPYs 7 and 8 from the meso-ester-substituted BODIPYs. Two feasible synthetic routes are developed successfully, including one short route with only three steps. The meso-COOH-substituted BODIPY 7 is completely soluble in pure water, and its fluorescence maximum reaches around 650 nm with a fluorescence quantum yield of up to 15 %. Time-dependent density functional theory calculations are conducted to understand the structure-optical properties relationship, and it is revealed that the Stokes shift is dependent mainly on the geometric change from the ground state to the first excited singlet state. Furthermore, cell staining tests demonstrate that the meso-ester-substituted BODIPYs (1 and 3-6) and one of the meso-COOH-substituted BODIPYs (8) are very membrane-permeable. These features make these meso-ester- and meso-COOH-substituted BODIPY dyes attractive for bioimaging and biolabeling applications in living cells. Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
KAUST Department:
KAUST Catalysis Center (KCC); Physical Sciences and Engineering (PSE) Division; Chemical Science Program; HCL
Publisher:
Wiley-Blackwell
Journal:
Chemistry - A European Journal
Issue Date:
21-Jan-2014
DOI:
10.1002/chem.201303868
Type:
Article
ISSN:
09476539
Sponsors:
The work was supported financially by the A*STAR BMRC grant (10/1/21/19/642), the Singapore-Peking-Oxford Research Enterprise (SPORE) (COY-15-EWI-RCFSA/N197-1), MOE Tier 2 grant (MOE2011-T2-2-130), and IMRE core funding (IMRE/13-1C0205).
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorNi, Yongen
dc.contributor.authorZeng, Lintaoen
dc.contributor.authorKang, Namyoungen
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorWang, Liangen
dc.contributor.authorZeng, Zebingen
dc.contributor.authorChang, Young-Taeen
dc.contributor.authorWu, Jishanen
dc.date.accessioned2015-08-03T11:46:18Zen
dc.date.available2015-08-03T11:46:18Zen
dc.date.issued2014-01-21en
dc.identifier.issn09476539en
dc.identifier.doi10.1002/chem.201303868en
dc.identifier.urihttp://hdl.handle.net/10754/563346en
dc.description.abstractA series of meso-ester-substituted BODIPY derivatives 1-6 are synthesized and characterized. In particular, dyes functionalized with oligo(ethylene glycol) ether styryl or naphthalene vinylene groups at the α positions of the BODIPY core (3-6) become partially soluble in water, and their absorptions and emissions are located in the far-red or near-infrared region. Three synthetic approaches are attempted to access the meso-carboxylic acid (COOH)-substituted BODIPYs 7 and 8 from the meso-ester-substituted BODIPYs. Two feasible synthetic routes are developed successfully, including one short route with only three steps. The meso-COOH-substituted BODIPY 7 is completely soluble in pure water, and its fluorescence maximum reaches around 650 nm with a fluorescence quantum yield of up to 15 %. Time-dependent density functional theory calculations are conducted to understand the structure-optical properties relationship, and it is revealed that the Stokes shift is dependent mainly on the geometric change from the ground state to the first excited singlet state. Furthermore, cell staining tests demonstrate that the meso-ester-substituted BODIPYs (1 and 3-6) and one of the meso-COOH-substituted BODIPYs (8) are very membrane-permeable. These features make these meso-ester- and meso-COOH-substituted BODIPY dyes attractive for bioimaging and biolabeling applications in living cells. Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.en
dc.description.sponsorshipThe work was supported financially by the A*STAR BMRC grant (10/1/21/19/642), the Singapore-Peking-Oxford Research Enterprise (SPORE) (COY-15-EWI-RCFSA/N197-1), MOE Tier 2 grant (MOE2011-T2-2-130), and IMRE core funding (IMRE/13-1C0205).en
dc.publisherWiley-Blackwellen
dc.subjectbioimagingen
dc.subjectBODIPYen
dc.subjectdyesen
dc.subjectfluorescent probesen
dc.subjectmembrane permeabilityen
dc.subjectnear-infrareden
dc.titleMeso-ester and carboxylic acid substituted BODIPYs with far-red and near-infrared emission for bioimaging applicationsen
dc.typeArticleen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentHCLen
dc.identifier.journalChemistry - A European Journalen
dc.contributor.institutionDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singaporeen
dc.contributor.institutionNUS Environmental Research Institute, National University of Singapore, 5A Engineering Drive 1, 02-01, Singapore 117411, Singaporeen
dc.contributor.institutionSchool of Chemical and Chemical Engineering, Tianjin University of Technology, Tianjin 300384, Chinaen
dc.contributor.institutionLaboratory of Bioimaging Probe Development, Singapore Bioimaging Consortium, ASTAR, Singaporeen
dc.contributor.institutionInstitute of Materials Research and Engineering, ASTAR, 3 Research Link, Singapore 117602, Singaporeen
kaust.authorHuang, Kuo-Weien
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