Authors:

Jayne L. Bishop

Date Created:

Not specified

Course Title:

Professor:

Not specified

About Paper:

Cytosolic pH plays a critical role in the normal function of cells, enzymes, and metabolic processes, as disruptions in pH have been proven to be correlated with neurological diseases, protein degradation, abnormal growth, and cancers. The synthesis of fluorescent pH sensors would provide a method for visualizing and quantifying pH disturbances, revealing major physiological issues and impaired cellular function in living organisms. Recent research has identified BODIPY compounds as excellent probes for biological sensing due to their high absorption coefficients and adaptability. Previously, our laboratory developed a series of new dibenzo-fused BODIPY compounds that exhibit bright emissions in the near-infrared "tissue-transparent" spectral region. These properties make them promising candidates for the development of optical sensors suitable for in vivo imaging applications. The primary objective of this project is to design a water-soluble, near-infrared BODIPY-based pH sensor that operates via a photoinduced electron transfer (PET) mechanism. The sensor design consists of a fluorescent dibenzo-BODIPY chromophore covalently linked to a pH-sensitive N,N-diethylamino aniline moiety. In previous work, our laboratory synthesized a series of such compounds in which the chromophore-to-receptor distance and the substituents on the N,N-diethylamino group were systematically varied. All compounds exhibited increased fluorescence intensity upon protonation of the diethylamino group with trifluoroacetic acid in organic solvents. The compounds that showed the most pronounced differences in fluorescence intensity between their protonated and non-protonated forms were selected for further modifications. In this research-in-progress report, we describe our efforts to modify functional groups on the dibenzo-BODIPY core and to introduce polyethylene glycol (PEG) linkers in order to improve the water solubility of the sensor.

Source:

Loyola University Chicago

Topics:

No topics listed

Co-authors:

Jayne L. Bishop