Mannose-functionalized diketopyrrolopyrrole as AIE-active probes for lectin detection and cancer cell imaging

[Display omitted] •Three diketopyrrolopyrrole-based AIE-active probes for lectin detection were reported.•DPP-M, DPPF-M, DPPS-M exhibited significant fluorescence enhancement towardsCon A.•Three probes showed selective recognition of Con A with nanomolar detection limits.•DPPS-M was successfully sta...

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Bibliographic Details
Published in:Sensors and actuators. B, Chemical Chemical, 2019-03, Vol.282, p.232-242
Main Authors: Wang, Jian, Hang, Yandi, Hua, Jianli
Format: Article
Language:English
Subjects:
AIE-active probe
Cancer
Chemical synthesis
Concanavalin A
Diketopyrrolopyrrole
Fluorescence
Lectins
Mannose
NIR region
Photon correlation spectroscopy
Proteins
Receptors
Sugar-lectin interactions
Tumors
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Summary:[Display omitted] •Three diketopyrrolopyrrole-based AIE-active probes for lectin detection were reported.•DPP-M, DPPF-M, DPPS-M exhibited significant fluorescence enhancement towardsCon A.•Three probes showed selective recognition of Con A with nanomolar detection limits.•DPPS-M was successfully stains cancer cells through interactions between mannoses and MRs. Considering that many malignant tumors overexpress the mannose receptors (MR) on the surface, mannosylated dyes can target tumor cells by using specific sugar-protein interactions. An AIE-active probe (DPPM) with two mannose groups based on diketopyrrolopyrrole (DPP) core have been developed in our previous work for probing the specific interactions. In order to evaluate the effects of the number of sugar groups on the probes performance and cell imaging, another two glyco-probes based on DPP conjugated with four (DPPF-M) and six (DPPS-M) mannose groups were designed and synthesized. All three molecules are AIE-active and can recognize concanavalin A (Con A) selectively with nanomolar limits of detection. The increasement of fluorescence of glyco-DPPs in NIR region with addition of lectins is attributed to the aggregates induced by sugar-lectin interactions, which has been determined via dynamic light scattering (DLS) and scanning electronic microscope (SEM) analysis. Since the multiple mannose-ligands on DPPS-M, it successfully stains cancer cells which are overexpressed with MRs on the surface such as MDA-MB-231 and MCF-7 cells through interactions between mannoses and MRs.
ISSN:0925-4005
1873-3077
DOI:10.1016/j.snb.2018.10.091