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The precise and fast detection of heparin, the most widely used anticoagulant, remains a significant challenge for assessing its use in a clinical setting. In this work, we adapt a well-established asymmetric cyanine fluorogenic platform for the purpose of ultrasensitive heparin detection in the presence of common interferant chemical species. Three analogous fluorescence probes are synthesized in order to optimize for the number of binding moieties. Their interaction with heparin is studied using steady-state absorption, fluorescence, and circular dichroism spectroscopy. The obtained probes exhibit a highly sensitive "turn-on" fluorescence response to heparin, with a LOD in the 10-25 nM range, well within practical requirement, as well as a visible colorimetric change. The heparin-probe complex is also employed as a sensitive detection platform for protamine, both in the "turn-off" fluorescence and ratiometric detection schemes.
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http://dx.doi.org/10.3390/molecules30030570 | DOI Listing |
J Med Chem
April 2025
Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, Chi
Developing small molecules that inherently integrate highly tumor-targeted near-infrared fluorescence (NIRF) imaging with potent therapeutic effects remains challenging in anticancer theranostics. Here, we synthesized and characterized a series of heptamethine cyanine PSs with symmetric and asymmetric structures. Among them, we first discovered that asymmetric structures significantly enhanced tumor targeting.
View Article and Find Full Text PDFBiosensors (Basel)
March 2025
Faculty of Chemistry and Pharmacy, Sofia University "St. Kliment Ohridski", 1 J. Bourchier Ave., 1164 Sofia, Bulgaria.
Two new asymmetric monomethine cyanine dyes, featuring dimethoxy quinolinium or methyl quinolinium end groups and benzothiazole or methyl benzothiazole end groups were synthesized. The chemical structures of the two dyes-()-6,7-dimethoxy-1-methyl-4-((3-methylbenzo[d]thiazol-2(3H)-ylidene)methyl)quinolin-1-ium iodide () and ()-4-((3,5-dimethylbenzo[d]thiazol-2(3H)-ylidene)methyl)-1,2-dimethylquinolin-1-ium iodide ()-were confirmed through NMR spectroscopy and MALDI-TOF mass spectrometry. A new methodology was developed to study monocationic dyes in the absence of a matrix and cationizing compounds in MALDI-TOF mass experiments.
View Article and Find Full Text PDFMolecules
January 2025
Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany.
The precise and fast detection of heparin, the most widely used anticoagulant, remains a significant challenge for assessing its use in a clinical setting. In this work, we adapt a well-established asymmetric cyanine fluorogenic platform for the purpose of ultrasensitive heparin detection in the presence of common interferant chemical species. Three analogous fluorescence probes are synthesized in order to optimize for the number of binding moieties.
View Article and Find Full Text PDFJ Med Chem
February 2025
Center for Advanced Materials Research & Faculty of Arts and Sciences, Beijing Normal University, Zhuhai 519087, China.
Fluorescence molecular imaging aims to enhance clarity in the region of interest, particularly in the near-infrared IIb window (NIR-IIb, 1500-1700 nm). To achieve this, we developed a novel small-molecule dye, named , based on classic cyanine dyes (heptamethine or pentamethine is essential for wavelengths beyond 1000 nm). By reducing excessive polymethine to a single methine and disrupting symmetry to form an asymmetric donor-π-acceptor (D-π-A) architecture, we enhanced the donor's electron-donating capability, yielding emission at 1088 nm.
View Article and Find Full Text PDFAnal Sci
May 2025
Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-Ku, Sendai, 980-8578, Japan.
The diverse functional roles of RNA within cells have led to a growing interest in developing RNA-binding fluorescent probes to investigate RNA functions. In particular, the probes for double-stranded RNA (dsRNA) structures are of significant value given the importance of the secondary and tertiary RNA structures on their biologic functions. This review highlights our recent efforts on the development of triplex-forming peptide nucleic acid (TFP)-based probes for fluorescence sensing of dsRNA structures.
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