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Kim, Dokyoung,Sambasivan, Sunderraman,Nam, Hyoseok,Hean Kim, Ki,Yong Kim, Jin,Joo, Taiha,Lee, Kyung-Ha,Kim, Kyong-Tai,Han Ahn, Kyo The Royal Society of Chemistry 2012 Chemical communications Vol.48 No.54
<P>Reaction-based fluorescent probes for monoamine oxidases A and B are developed based on a new two-photon absorbing compound and its precursor. The probes show turn-on fluorescence response to the enzymes owing to the two-photon absorbing compound produced by the enzymatic activity, as monitored by one- as well as two-photon microscopy for the first time.</P> <P>Graphic Abstract</P><P>Reaction-based fluorescent probes for monoamine oxidases A and B are developed based on a new two-photon absorbing compound and its precursor. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=c2cc32424e'> </P>
A structural remedy toward bright dipolar fluorophores in aqueous media
Singha, Subhankar,Kim, Dokyoung,Roy, Basab,Sambasivan, Sunderraman,Moon, Hyunsoo,Rao, Alla Sreenivasa,Kim, Jin Yong,Joo, Taiha,Park, Jae Woo,Rhee, Young Min,Wang, Taejun,Kim, Ki Hean,Shin, Youn Ho,Jun Royal Society of Chemistry 2015 Chemical Science Vol. No.
<▼1><P>Structural factors governing the poor emission of dipolar dyes in aqueous media are identified, leading to new acedan derivatives with brighter fluorescence and enhanced two-photon properties.</P></▼1><▼2><P>The donor–acceptor (D–A) type dipolar fluorophores, an important class of luminescent dyes with two-photon absorption behaviour, generally emit strongly in organic solvents but poorly in aqueous media. To understand and enhance the poor emission behaviour of dipolar dyes in aqueous media, we undertake a rational approach that includes a systematic structure variation of the donor, amino substituent of acedan, an important two-photon dye. We identify several factors that influence the emission behaviour of the dipolar dyes in aqueous media through computational and photophysical studies on new acedan derivatives. As a result, we can make acedan dyes emit bright fluorescence under one- and two-photon excitation in aqueous media by suppressing the liable factors for poor emission: 1,3-allylic strain, rotational freedom, and hydrogen bonding with water. We also validate that these findings can be generally extended to other dipolar fluorophores, as demonstrated for naphthalimide, coumarin and (4-nitro-2,1,3-benzoxadiazol-7-yl)amine (NBD) dyes. The new acedan and naphthalimide dyes thus allow us to obtain much brighter two-photon fluorescent images in cells and tissues than in their conventional forms. As an application of these findings, a thiol probe is synthesized based on a new naphthalimide dye, which shows greatly enhanced fluorescence from the widely used <I>N</I>,<I>N</I>-dimethyl analogue. The results disclosed here provide essential guidelines for the development of efficient dipolar dyes and fluorescence probes for studying biological systems, particularly by two-photon microscopy.</P></▼2>