Classification and naming of polymethine dyes used as staining agents for microscopy. A short guide for biomedical investigators

Abstract

ABSTRACT The scientific literature contains many accounts of application of polymethine dyes, including cyanine dyes, as imaging agents, i.e., “biological stains,” for microscopic investigation of biological materials. Currently, many such dyes are used as probes for living cells, i.e., “fluorescent probes.” Polymethine dyes are defined here by two criteria. First, they possess a conjugated chain of (2n + 1) sp2-hybridized carbon atoms that connect a terminal π-electron-accepting (π-electron withdrawing) group with a terminal π-electron-donating group. Second, they have an odd number (2n + 3) of π-centers and an even number (2n + 4) of π-electrons in this chain, where n equals the number of –CR2=CR3– groups, usually vinylene groups –CH=CH–. Commercialization of diverse chemical types of many polymethine dyes has been attempted. The dyes that have achieved wide application, however, are limited in number and it is these dyes that are emphasized here. Because these polymethine dyes sometimes have been described by confusing, and sometimes confused, names, we clarify here the chemical categories and names of such dyes for the nonchemist, biomedical end user of such imaging agents. Nevertheless, the nomenclature presented here is not intended to replace the traditional “chromophore” categories of dyestuff chemistry, because the latter are held in place both by wide usage and by venerable authorities, such as the Colour Index.