K.M.K. Swamy

Manipulation of fluorescent and colorimetric changes of fluorescein derivatives and applications for sensing silver ions

Three structurally similar compounds, , bearing a fluorescence chromophore to which are appended morpholine, thiomorpholine and methylpiperazine substituents, display opposite fluorescence responses to pH changes, in contrast to that observed for fluorescein; and have extremely high binding selectivity towards Ag(+) ions and show completely different fluorescent and colorimetric changes upon addition of Ag(+), and the differences are proposed to be associated with different binding modes of and to this metal ion.

Selective homocysteine turn-on fluorescent probes and their bioimaging applications

The design and development of new pyrene-based fluorescent probes, P-Hcy-1 and P-Hcy-2, which display selective fluorescence enhancements in response to homocysteine (Hcy), are described. The distinctly different fluorescence responses of P-Hcy-1 and P-Hcy-2 to Hcy vs. Cys are explained by theoretical calculations. Finally, the results of cell experiments show that these probes can be used to selectively detect Hcy in mammalian cells.

A Selective Imidazoline-2-thione-Bearing Two-Photon Fluorescent Probe for Hypochlorous Acid in Mitochondria

Hypochlorite (OCl(-)) plays a key role in the immune system and is involved in various diseases. Accordingly, direct detection of endogenous OCl(-) at the subcellular level is important for understanding inflammation and cellular apoptosis. In the current study, a two-photon fluorescent off/on probe (PNIS) bearing imidazoline-2-thione as an OCl(-) recognition unit and triphenylphosphine (TPP) as a mitochondrial-targeting group was synthesized and examined for its ability to image mitochondrial OCl(-) in situ. This probe, based on the specific reaction between imidazoline-2-thione and OCl(-), displayed a selective fluorescent off/on response to OCl(-) with the various reactive oxygen species in a physiological medium. PNIS was successfully applied to image of endogenously produced mitochondrial OCl(-) in live RAW 264.7 cells via two-photon microscopy.

Recent Development of Anion Selective Fluorescent Chemosensors

Sensing anions via fluorescence changes has been an active research target in recent years due to its simplicity and the high detection limits this approach permits. In this mini review, we cover the recent development of anion selective fluorescent chemosensors reported from our group. We classify the anion selective fluorescent chemosensors according to their topology and structure, which includes urea or thiourea derivatives, imidazolium derivatives, Zn-DPA derivatives and boronic acid modified systems.

Highly selective ratiometric fluorescent probe for Au3+ and its application to bioimaging

The 4-propargylamino-1,8-naphthalimide based fluorescent probe 1 has been explored as a sensor for selective detection of Au(3+). 4-Amino-1,8-naphthalimides, that possess typical intramolecular charge transfer (ICT) electronic characteristics, have been widely used as versatile platforms for fluorescent probes. The newly designed probe 1 contains a propargylamine moiety at C-4 of the naphthalimide chromophore that reacts with Au(3+) to generate a product that has distinctly different electronic properties from 1. Specifically, the probe undergoes a remarkable change in its absorption spectrum upon addition of Au(3+) that is associated with a distinct color change from yellow to light pink. In addition, a blue shift of ca. 56 nm also takes place in the emission spectra of the probe. Consequently, 1 serves as a reaction-based sensor or so called chemodosimeter for Au(3+). Importantly, surfactants enhance the rate of reaction of 1 with Au(3+), thus, enhancing its use as a real time sensor. Finally, the results of studies probing its application to bioimaging of Au(3+) in live cells show that the probe 1 has a unique ability to sense Au(3+) in cells and, in particular, in lipid droplets within cells.

Recent Progress in Fluorescent Imaging Probes

Due to the simplicity and low detection limit, especially the bioimaging ability for cells, fluorescence probes serve as unique detection methods. With the aid of molecular recognition and specific organic reactions, research on fluorescent imaging probes has blossomed during the last decade. Especially, reaction based fluorescent probes have been proven to be highly selective for specific analytes. This review highlights our recent progress on fluorescent imaging probes for biologically important species, such as biothiols, reactive oxygen species, reactive nitrogen species, metal ions including Zn2+, Hg2+, Cu2+ and Au3+, and anions including cyanide and adenosine triphosphate (ATP).

Effective Strategy for Colorimetric and Fluorescence Sensing of Phosgene Based on Small Organic Dyes and Nanofiber Platforms

Three o-phenylendiamine (OPD) derivatives, containing 4-chloro-7-nitrobenzo[c][1,2,5]oxadiazole (NBD-OPD), rhodamine (RB-OPD), and 1,8-naphthalimide (NAP-OPD) moieties, were prepared and tested as phosgene chemosensors. Unlike previously described methods to sense this toxic agent, which rely on chemical processes that transform alcohols and amines to respective phosphate esters and phosphoramides, the new sensors operate through a benzimidazolone-forming reaction between their OPD groups and phosgene. These processes promote either naked eye visible color changes and/or fluorescence intensity enhancements in conjunction with detection limits that range from 0.7 to 2.8 ppb. NBD-OPD and RB-OPD-embedded polymer fibers, prepared using the electrospinning technique, display distinct color and fluorescence changes upon exposure to phosgene even in the solid state.

Colorimetric Detection of Thiophenol Based on a Phenolphthalein Derivative and Its Application as a Molecular Logic Gate

A phenolphthalein-based colorimetric probe bearing a dinitrobenzene group is reported as a thiophenol (PhSH)-selective chemodosimeter. PhSH can react with chemodosimeter 1 to afford phenolphthalein. The addition of PhSH to the aqueous solution of 1 followed by a change in pH of the resulting solution to basic induces a selective color change from colorless to pink. Furthermore, using PhSH and base as inputs and color change of 1 by naked eye as an output, leads to the construction of an AND logic gate.