Design, synthesis of novel small-molecular fluorescent sensors for the detection of biologically important analytes and mitochondria-targeted pH probe

Abstract

its prevention is highly important for in vivo and in vitro research in biological milieu. Owing to the positively charged system in the probe which causes its strong overlap in mitochondria in particular, it is analyzed with the help of Mito-Tracker deep red (Pearson’s coefficient = 0.798). Surprisingly, BICBzBF exhibits a dynamic and rapid response to peroxynitrite < 120 s with a low detection limit (60.5 nM) over other biologically competitive interferents in vitro and displays endogenous performance satisfactorily as well. Moreover, BICBzBF dynamically detected peroxynitrite with distinct and significantly red fluorescence in inflammation zebrafish models (Danio rerio).

The rational design of the mitochondria-accessible and highly photostable fluorogenic probe BICBzDP was synthesized. It displays a high selectivity and sensitivity towards ONOO- which triggers the diphenyl phosphinate receptor and led to enhancement by the way of an ICT photo mechanism. In addition, a sulfonate group was present to help improve water solubility, a strategy used to help avoid chemical aggregation in aqueous media

their electrostatics helps probe largely distributed in the mitochondria and further confirmed with the overlapping of Mito-Tracker deep red (Pearson’s coefficient = 0.87). Interestingly, BICBzDP expresses the nanomolar detection limit (49.9 nM) and shows efficient performance in endogenous as well. Besides, BICBzDP was efficaciously functionalized in inflammatory zebrafish models (Danio rerio) to help detect ONOO$^-$ with a distinctive red fluorescence.

A novel design featuring excellent water-soluble and mitochondria-accessibility an “OFF-ON” fluorogenic sensor TPP-MpH amalgamated with a glycol chain and hydrophilic triphenylphosphine cation moiety was synthesized for mitochondrial pH regulation. Seeing as pH is an important key factor for the normal functions in living organisms, and even minute fluctuations over time, it may cause many relevant diseases. Consequently, accurate observation of mitochondrial pH in the physiopathological milieu is strongly required. Here, we fabricated a new structurally characterized and highly reversible fluorogenic sensor which includes phenol as a pH-responsive moiety

In the last two decades, the emergent role of fluorogenic sensors in the field of diagnosis, biomedical treatment

as well as in the detection of environmentally important analytes has tremendous demand among scientific researchers. Specifically, the design and synthesis of novel fluorogenic probes are highly convenient to detect biologically important analytes (ROS/RNS) owing to their excellent selectivity, high sensitivity, ease of operational technique, and real-time visualization in vivo.

A novel and highly photostable BICBzBF fluorometric sensor which targets mitochondria specifically for dynamic detection of peroxynitrite which triggers the aryl boronate group and proceeding to ICT photo mechanism was designed and synthesized. In this system, the sulfonate group was specifically incorporated in the fluorogenic probe to help it evade chemical self-aggregation in aqueous media which is a ready occurrence and needs to be prevented

water solubility is a major aspect of in vivo and in vitro studies. Due to mitochondrial matrix has negative potential and BICBzDP has a positively charged nitrogen atom

fluorescence is owing to pH variation giving a pale yellow colour (acidic media), and amaranth colour (basic media). The calculated pK$_a$ value of TPP-MpH was found to be 7.24. Besides, a portable and low-cost pH test paper, acid-base vapor detection along naked-eye colorimetric analysis combination makes TPP-MpH the utmost suitable analytical tools to help monitor environmental and biological pH changes.

It is a genuine pleasure to express my deep sense of thanks to the Korean Government Scholarship Program (KGSP) for providing a scholarship for the Ph.D. and KAIST for the fellowship and research facilities.

The author of this thesis is a Global Korea Scholarship scholar sponsored by the Korean Government.