Caged rhodamine-based fluorescent probe for biothiol: Selective detection of cysteine over homocysteine and glutathione in water

Lim, Soo-Yeon; Yoon, Doo‐Ha; Ha, Do Yeon; Ahn, Jung mo; Kim, Dae Il; Kown, Hyockman; Ha, Hyun‐Joon; Kim, Hae-Jo

doi:10.1016/j.snb.2013.06.101

Cited by 48 publications

(12 citation statements)

References 26 publications

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“…As shown in Figure , spectroscopic changes in DCM-S-PPT treated with Cys or Hcy could be observed similar to those exposed to GSH. These results were expected because the thiol-containing structures of Cys and Hcy are identical to that of GSH. − However, there were no obvious spectroscopic changes observed upon exposure to other amino acids without thiol, K + , Ca 2+ , Na + , and Mg 2+ , so the disulfide bond cleavage in DCM-S-PPT was selective for the thiol species. According to Figure S6, the reaction constants of DCM-S-PPT reaction with GSH, Cys, and Hcy are 0.027, 0.015, and 0.016 min –1 , respectively (Figure S9).…”

Section: Resultsmentioning

confidence: 83%

GSH-Activated NIR Fluorescent Prodrug for Podophyllotoxin Delivery

Liu

Zhu

et al. 2017

ACS Appl. Mater. Interfaces

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Theranostic prodrug therapy enables the targeted delivery of anticancer drugs with minimized adverse effects and real-time in situ monitoring of activation of the prodrugs. In this work, we report the synthesis and biological assessment of the near-infrared (NIR) prodrug DCM-S-PPT and its amphiphilic copolymer (mPEG-DSPE)-encapsulated nanoparticles. DCM-S-PPT is composed of podophyllotoxin (PPT) as the anticancer moiety and a dicyanomethylene-4H-pyran (DCM) derivative as the NIR fluorescent reporter, which are linked by a thiol-specific cleavable disulfide bond. In vitro experiments indicated that DCM-S-PPT has low cytotoxicity and that glutathione (GSH) can activate DCM-S-PPT resulting in PPT release and a concomitant significant enhancement in NIR fluorescence at 665 nm. After being intravenously injected into tumor-bearing nude mice, DCM-S-PPT exhibited excellent tumor-activated performance. Furthermore, we have demonstrated that mPEG-DSPE as a nanocarrier loaded with DCM-S-PPT (mPEG-DSPE/DCM-S-PPT) showed even greater tumor-targeting performance than DCM-S-PPT on account of the enhanced permeability and retention effect. Its tumor-targeting ability and specific drug release in tumors make DCM-S-PPT a promising prodrug that could provide a significant strategy for theranostic drug delivery systems.

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Section: Resultsmentioning

confidence: 83%

GSH-Activated NIR Fluorescent Prodrug for Podophyllotoxin Delivery

Liu

Zhu

et al. 2017

ACS Appl. Mater. Interfaces

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“…A glutathione-protected silver nanocluster was first used for the detection of Cys [38]. Also, a rhodamine-based fluorescent probe masked with a para-hydroxybenzyl alcohol can discriminate Cys over Hcy/GSH in HEPES buffer through a series of reactions of Michael addition, intramolecular cyclization and the deprotection [39]. In addition, three coumarin fluorophore cationic probes were designed based on a response-assisted electrostatic attraction strategy, and enabled response to Cys in aqueous solution [40].…”

Section: Introductionmentioning

confidence: 99%

A ratiometric fluorescent probe for cysteine and its application in living cells

Dai

Zhang

Liu

et al. 2015

Sensors and Actuators B: Chemical

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“…Among these various strategies, fluorescent probes for the detection of biothiols have been developed quickly because of the method's ease of operation, high selectivity, sensitivity, low cost, low detection limits and potential for in vivo imaging (24)(25)(26). Therefore, various fluorescent probes for biothiols based on different fluorophores have been constructed, including rhodamine (27)(28)(29), naphthalimide (30), BODIPY (31,32), fluorescein (33)(34)(35)(36), cyanine (37)(38)(39), flavone (40,41) and coumarin (42)(43)(44)(45)(46)(47)(48)(49)(50). Of these, coumarin dye is one of the molecules used most widely in fluorescent probes owing to its high photostability, large Stokes shift, high cell permeability, visible emission wavelength and high fluorescence quantum yield (51,52).…”

Section: Introductionmentioning

confidence: 99%

A coumarin‐based fluorescent turn‐on probe for detection of biothiols in vitro

Liu

Jiang

et al. 2015

Luminescence

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A novel fluorescent probe (CA-N) was designed and synthesized for detection of biothiols. CA-N displayed a strong fluorescence in the presence of biothiols with high sensitivity, and the mechanism for detection biothiols was based on the Michael addition reaction of a thiol group to α,β-unsaturated ketones. CA-N showed low detection limit for cysteine (Cys), homocysteine (Hcy), and glutathione (GSH), which were calculated as 3.16, 0.19 and 5.15 μM, respectively. At the same time, CA-N exhibited high selectivity toward biothiols compared with other biological amino acids. In vitro cell experiments proved that CA-N had no cytotoxicity, high cell permeability and could be employed in living cell imaging for biothiols.

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Caged rhodamine-based fluorescent probe for biothiol: Selective detection of cysteine over homocysteine and glutathione in water

Cited by 48 publications

References 26 publications

GSH-Activated NIR Fluorescent Prodrug for Podophyllotoxin Delivery

GSH-Activated NIR Fluorescent Prodrug for Podophyllotoxin Delivery

A ratiometric fluorescent probe for cysteine and its application in living cells

A coumarin‐based fluorescent turn‐on probe for detection of biothiols in vitro

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