Novel near-infrared pyrimidine-fused pH fluorescent probes were prepared by an unusual barbiturate-mediated debenzoindolation and subsequent heteroannulation. A plausible mechanistic pathway is proposed, and the final structures were further elucidated by 2D-NMR. All new compounds are highly fluorescent in the near-infrared region and possess excellent spectral sensitivities to environmental pH changes.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2725187PMC
http://dx.doi.org/10.1021/ol802363xDOI Listing

Publication Analysis

Top Keywords

near-infrared fluorescent
4
fluorescent ph-sensitive
4
ph-sensitive probes
4
probes unexpected
4
unexpected barbituric
4
barbituric acid
4
acid mediated
4
mediated synthesis
4
synthesis novel
4
novel near-infrared
4

Similar Publications

Both photothermal therapy (PTT) and chemodynamic therapy (CDT) are designed to focus their antitumor effect on only the tumor site, thereby minimizing unwanted severe damage to healthy tissue outside the tumor. However, each monotherapy is limited in achieving complete tumor eradication, resulting in tumor recurrence. The combination of multiple therapies may help to overcome the limitations of single therapy, improve the chances of complete tumor eradication, and reduce the risk of recurrence.

View Article and Find Full Text PDF

Rationally manipulating molecular planarity to improve molar absorptivity, NIR-II brightness, and photothermal effect for tumor phototheranostics.

Biomaterials

January 2025

Lab of Molecular Imaging and Translational Medicine (MITM), Engineering Research Center of Molecular and Neuro Imaging, Ministry of Education, School of Life Science and Technology, Xidian University & International Joint Research Center for Advanced Medical Imaging and Intelligent Diagnosis and Treatment, Xi'an, Shaanxi, 710126, China. Electronic address:

The secondary near-infrared region (NIR-II) fluorescence imaging-guided photothermal therapy (PTT) offers a noninvasive and light-controllable treatment option for deep-seated cancers. However, the development of NIR-II photothermal agents (NIR-II PTAs) that possess the desired properties of high molar absorption coefficient (ε), fluorescence quantum yield (QY), and photothermal conversion efficiency (PCE) remain a challenge due to the contradiction between radiative and nonradiative processes. Herein, we propose a novel side-chain heteroatom substitution engineering strategy to simultaneously enhance ε, QY, and PCE by modifying the molecular planarity.

View Article and Find Full Text PDF

Cathepsin B dependent activatable trigger fluorophore (CAT-Fluor) for in situ functional imaging of antibody-drug conjugates.

Biosens Bioelectron

January 2025

Deparment of Pharmacy, the Second Affiliated Hospital, Zhejiang University School of Medicine and College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, 310058, China. Electronic address:

Antibody-drug conjugates (ADC) have emerged as an important class of therapeutic agents that combine the target specificity of a monoclonal antibody with the potency of a cytotoxic payload. Despite clinical success, our understanding of receptor endocytosis and ADC toxicity remains limited. Less than 1% of ADCs reach tumors, raising concerns about off-target cytotoxicity.

View Article and Find Full Text PDF

Near-infrared spectroscopy discriminates mass-reared sterile and wild tsetse flies.

PLoS Negl Trop Dis

January 2025

Institut de Recherche en Sciences de la Santé, Direction Régionale, Bobo-Dioulasso, Burkina Faso.

Background: Monitoring the efficacy of the sterile insect technique (SIT) programs, it is desirable to discriminate between wild and sterile tsetse males captured in monitoring traps. Currently, this is primarily achieved by marking sterile males with fluorescent dye powder before release, and identifying them using a fluorescence camera and/or microscope. However, the accuracy of this method is limited due to defective marking and wild flies contaminated with a few dye particles in the monitoring traps.

View Article and Find Full Text PDF

Design strategies and biomedical applications of organic NIR-IIb fluorophores.

Chem Commun (Camb)

January 2025

Marshall Laboratory of Biomedical Engineering, International Cancer Center, Guangdong Key Laboratory for Biomedical Measurements and Ultrasound Imaging, Laboratory of Evolutionary Theranostics (LET), School of Biomedical Engineering, Shenzhen University Medical School, Shenzhen University, Shenzhen 518055, China.

The introduction of fluorescence imaging (FLI) in near-infrared II sub-channels (NIR-IIb, 1500-1700 nm) has revolutionized the ability to explore complex patho-physiological settings . Despite the transformative potentials, the development of organic NIR IIb dyes encounters considerable difficulties, and only a limited number of such fluorophores have been developed so far. This review systematically introduces design strategies of organic NIR-IIb fluorophores classified by molecular scaffolds, mainly including cyanine dyes and D-A-D small molecule dyes.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!