Azobenzene-based chloride transporters with light-controllable activities

Choi, Ye Rin; Kim, Gyu Chan; Jeon, Hae Geun; Park, Jin‐Hong; Namkung, W.; Jeong, Kyu Sung

doi:10.1039/c4cc07560a

Cited by 78 publications

(56 citation statements)

References 49 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Choi et al 90 continued their work on anion transport using two urea and thiourea binding motifs appended to the photoresponsive diazobenzene scaffold ( Figure 62). Proton NMR titration studies with tetrabutylammonium chloride in DMSO-d 6 /CDCl 3 (1:9, v/v) with 0.1% water showed a clear trend of stronger binding toward the cis-isomers than the corresponding trans-isomers by one order of magnitude.…”

Section: Transmembrane Anion Transportmentioning

confidence: 97%

Anion Receptor Chemistry

Gale

Howe

2016

Chem

374

228

View full text Add to dashboard Cite

Section: Transmembrane Anion Transportmentioning

confidence: 97%

Anion Receptor Chemistry

Gale

Howe

2016

Chem

374

228

View full text Add to dashboard Cite

“…[14] Photoisomerization of molecules has also been used to activate or deactivate channel/carrier-mediated-ion transport. [15] Herein, we have introduced the "photocleavable prodrug" concept into the domain of artificial ion transporters and developed ap rocarrier that undergoes photo-controlled release of an active carrier to induce chloride-mediated cell death. Photocleavable protecting groups have been known in organic synthesis for several decades, [16] and have attracted renewed interest in recent years due to their extensive applications in biology.…”

mentioning

confidence: 99%

Phototriggered Release of a Transmembrane Chloride Carrier from an o‐Nitrobenzyl‐Linked Procarrier

Salunke

Talukdar

2019

Angew Chem Int Ed

View full text Add to dashboard Cite

While there have been many studies on synthetic chloride carriers and ar ecent application for apoptotic cell death, so far,t he proposed huge potential of these systems in targeting cancer has not been realized due to their cytotoxicity to healthy cells.H erein, we describe the development of an indole-2-carboxamide receptor as an efficient membrane chloride carrier while the corresponding o-nitrobenzyl-linked derivative is ap rocarrier of the ion. Photoirradiation of the procarrier in liposomes results in release of the active carrier with up to 90 %t ransport efficiency.S uch photorelease of the carrier also works within cancer cells,resulting in efficient cell killing.Suchphotocleavable procarriers have great potential as ap hotodynamic therapyt oc ombat various types of cancers.

show abstract

“…Recently, enzymes (esterase and glycosylase) were used for releasing an active ion carrier from a procarrier (the inactive form of the carrier molecule) . Photoisomerization of molecules has also been used to activate or deactivate channel/carrier‐mediated‐ion transport …”

Section: Figurementioning

confidence: 99%

Phototriggered Release of a Transmembrane Chloride Carrier from an o‐Nitrobenzyl‐Linked Procarrier

Salunke

Talukdar

2019

Angewandte Chemie

View full text Add to dashboard Cite

While there have been many studies on synthetic chloride carriers and a recent application for apoptotic cell death, so far, the proposed huge potential of these systems in targeting cancer has not been realized due to their cytotoxicity to healthy cells. Herein, we describe the development of an indole‐2‐carboxamide receptor as an efficient membrane chloride carrier while the corresponding o‐nitrobenzyl‐linked derivative is a procarrier of the ion. Photoirradiation of the procarrier in liposomes results in release of the active carrier with up to 90 % transport efficiency. Such photorelease of the carrier also works within cancer cells, resulting in efficient cell killing. Such photocleavable procarriers have great potential as a photodynamic therapy to combat various types of cancers.

show abstract

Azobenzene-based chloride transporters with light-controllable activities

Abstract: Synthetic chloride transporters containing two urea groups linked through a diazobenzene spacer have been prepared and the trans-to-cis isomerization by light stimulation results in dramatic changes in the chloride transport activities across lipid and cell membranes.

Cited by 78 publications

References 49 publications

Anion Receptor Chemistry

Anion Receptor Chemistry

Phototriggered Release of a Transmembrane Chloride Carrier from an o‐Nitrobenzyl‐Linked Procarrier

Phototriggered Release of a Transmembrane Chloride Carrier from an o‐Nitrobenzyl‐Linked Procarrier

Contact Info

Product

Resources

About