@article {46192,
	title = {Ionic pyridinium-oxazole dyads: design, synthesis, and application in mitochondrial imaging},
	journal = {Journal of Organic Chemistry},
	volume = {84},
	year = {2019},
	month = {FEB },
	pages = {1766-1777},
	type = {Article},
	abstract = {<p>We recently developed an oxidative intramolecular 1,2-amino-oxygenation reaction, combining gold(I)/gold(III) catalysis, for accessing structurally unique ionic pyridinium-oxazole dyads (PODs) with tunable emission wavelengths. On further investigation, these fluorophores turned out to be potential biomarkers; in particular, the one containing -NMe2 functionality (NMe2-POD) was highly selective for mitochondrial imaging. Of note, because of mitochondria{\textquoteright}s involvement in early-stage apoptosis and degenerative conditions, tracking the dynamics of mitochondrial morphology with such imaging technology has attracted much interest. Along this line, we wanted to build a library of such PODs which are potential mitochondria trackers. However, Au/Selecfluor, our first-generation catalyst system, suffers from undesired fluorination of electronically rich PODs resulting in an inseparable mixture (1:1) of the PODs and their fluorinated derivatives. In our attempt to search for a better alternative to circumvent this issue, we developed a second-generation approach for the synthesis of PODs by employing Cu(II)/PhI(OAC)(2)-mediated oxidative 1,2-amino-oxygenation of alkynes. Thes newly synthesized PODs exhibit tunable emissions as well as excellent quantum efficiency up to 0.96. Further, this powerful process gives rapid access to a library of NMe2-PODs which are potential mitochondrial imaging agents. Out of the library, the randomly chosen POD-3g was studied for cell-imaging experiments which showed high mitochondrial specificity, superior photostability, and appreciable tolerance to microenvironment changes with respect to commercially available MitoTracker green.</p>
},
	issn = {0022-3263},
	doi = {10.1021/acs.joc.8b02528},
	author = {Shaikh, Aslam C. and Varma, Mokshada E. and Mule, Ravindra D. and Banerjee, Somsuvra and Kulkarni, Prasad P. and Patil, Nitin T.}
}
