Determination of non-traditional intrinsic fluorescence (NTIF) emission sites in 1-(4-carbomethoxypyrrolidone)-PAMAM dendrimers using CNDP-based quenching studies

Konopka, Małgorzata; Janaszewska, Anna; Johnson, Kayla A; Hedstrand, David M.; Tomalia, Donald A.; Klajnert‐Maculewicz, Barbara

doi:10.1007/s11051-018-4310-7

Cited by 19 publications

(23 citation statements)

References 31 publications

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“…8,25,26 More recently, we have shown that fluorescence intensity of the nanoparticle is enhanced considerably when the surface amines of the PAMAM dendrimer are converted to N-(4carbomethoxy)pyrrolidone groups (4-CMP). 27,28 Linear or branched polymers containing pyrrolidone moieties are well known for their dipolar aprotic properties, high solubility in organic solvents or water, as well as unusual biological compatibility, which allow them to be used in pharmaceutical formulations as excipients. 29 Their other applications include use as emulsifiers, stabilizers, dispersing agents, solubility enhancers, or surfactants.…”

Section: ■ Introductionmentioning

confidence: 99%

Non-Traditional Intrinsic Luminescence (NTIL): Dynamic Quenching Demonstrates the Presence of Two Distinct Fluorophore Types Associated with NTIL Behavior in Pyrrolidone-Terminated PAMAM Dendrimers

et al. 2019

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Historically, poly(amidoamine) (PAMAM) dendrimers were the first macromolecular structures reported to exhibit "non-traditional intrinsic luminescence" (NTIL) properties. Initially, this unique intrinsic luminescent property suggested the possibility of dendrimer-based biological imaging without the need for conjugating external labels. Unfortunately, low NTIL intensity levels exhibited by most simple surface-modified PAMAMs presented a serious barrier to progress in that area. Unexpectedly, a simple surface modification of amine-terminated PAMAM dendrimers with N-(4-carbomethoxy)pyrrolidone groups (4-CMP) was found to dramatically increase NTIL fluorescence intensity (i.e., >50-fold) while substantially enhancing biocompatibility and reducing cytotoxicity/complement activation properties. This current study focuses on the use of conventional and time-resolved spectroscopic measurements to characterize the NTIL behavior of 4-CMP PAMAM dendrimers over four generation levels (i.e., G2−G5). We describe and discuss the impact of polymer size and composition on NTIL intensity levels and quantum yields. Fluorescence lifetime measurements revealed two discrete major lifetime components, which were similar for all dendrimer generations and remained unaffected by changes in pH. Time-resolved fluorescence quenching studies involving a collisional quencher (methyl red) and a dynamic proximity quencher (nitrobenzoxadiazole dipeptide derivative) provided evidence for two spatially separated NTILtype emission sites within this 4-CMP PAMAM dendrimer series. In summary, these results provide important insights into the molecular-level NTIL mechanism and demonstrate the critical role of pyrrolidone surface modification as well as separate contributions made by interior dendrimer components to the observed enhancement of NTIL fluorescence intensity.

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Section: ■ Introductionmentioning

confidence: 99%

Non-Traditional Intrinsic Luminescence (NTIL): Dynamic Quenching Demonstrates the Presence of Two Distinct Fluorophore Types Associated with NTIL Behavior in Pyrrolidone-Terminated PAMAM Dendrimers

et al. 2019

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“…The above special features in the changing from solution to gel are presumed to be mainly due to the abnormal emissive mechanism for amine‐containing NTIL compounds, namely, aggregates of amine groups act as the real fluorescent centers. [ 15,16,25,31–33 ] In solution, fluorescent centers exist in a relatively relaxed microenvironment, the amine groups in aggregates usually undergo dynamic movements in a much larger space, and the loose and flexibly structure will cause more extended electron delocalization and the varied excited status with many different energy levels, resulting in the longer‐wavelength fluorescent peak and EDF. On the contrary, in hydrogel, most amine groups are anchored in 3D network, which affecting the fluorescent behaviors in two aspects.…”

Section: Resultsmentioning

confidence: 99%

Unique Property of Nontraditional Intrinsic Luminescence in the Transforming of Solution‐Hydrogel‐Solid and Its Applications

Wang

Lan

Zhang

et al. 2021

Macro Chemistry & Physics

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For the unusual phenomenon of nontraditional intrinsic luminescence, a systematic fluorescence study is conducted in the phase transformation from solution through hydrogel to solid states. In this process, significant differences are found in fluorescence intensity, peak position, lifetime, and excitation‐dependent emission. In particular, the samples in the hydrogel state show two fluorescent peaks at 480 and 516 nm, respectively, while only one fluorescent peak is detected in the cases of solution (at 516 nm) or solid (at around 450 nm). More interestingly, the longer wavelength peak presents excitation‐dependent fluorescence, and the shorter one is excitation‐independent. These unique fluorescent observations can be ascribed to the fact that the aggregates of amine groups act as the actual fluorescent centers, which are quite sensitive to their surrounding microenvironments. Based on these results, some simulation tests of sensors and intelligent hydrogels in response to water are also studied.

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“…PURE dendrimers have a pH-dependent blue fluorescence. The fluorescence of dendrimers and other polymers without possessing classic chromophores, referred as a NTIL, has been widely observed and reported. − Similar to its counterparts, PURO biodendrimers also show a blue fluorescence. However, the emission intensity is higher and permanent, not being influenced by pH changes (both in intensity and emission wavelength).…”

Section: Resultsmentioning

confidence: 99%

Osteogenic Differentiation of Human Mesenchymal Stem Cells by the Single Action of Luminescent Polyurea Oxide Biodendrimers

Pires

Conde

Bonifácio

2020

ACS Appl. Bio Mater.

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Polyurea oxide (PURO) biodendrimers are a class of dendrimers that can trigger osteogenic differentiation of human mesenchymal stem cells (hMSCs). PURO biodendrimers are prepared by simple, solventless oxidation of polyurea dendrimers using hydrogen peroxide as the oxidant in quantitative yield, retaining both biocompatibility (up to 10 mg/mL for higher generations) and the non-traditional intrinsic luminescence. The effect of PURO biodendrimers in the differentiation of hMSCs was found by the single addition to a standard growth medium for MSCs differentiation (without differentiation inducers). After 21 days of incubation, the formation of osteoblasts was confirmed by the alizarin red staining assay and alkaline phosphatase activity. This is the first report of in vitro osteodifferentiation fully regulated by synthetic soft polymers such as dendrimers. Current osteogenic differentiation protocols rely on an in vitro inducing formulation (including dexamethasone, ascorbic acid, and β-glycerophosphate), which lacks therapeutic potential in vivo. The outstanding role of dendrimers in nanomedicine, under clinic translation, combined with this feature is envisaged to foster PURO dendrimers as an important strategy in cell therapy and regenerative medicine.

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Determination of non-traditional intrinsic fluorescence (NTIF) emission sites in 1-(4-carbomethoxypyrrolidone)-PAMAM dendrimers using CNDP-based quenching studies

Cited by 19 publications

References 31 publications

Non-Traditional Intrinsic Luminescence (NTIL): Dynamic Quenching Demonstrates the Presence of Two Distinct Fluorophore Types Associated with NTIL Behavior in Pyrrolidone-Terminated PAMAM Dendrimers

Non-Traditional Intrinsic Luminescence (NTIL): Dynamic Quenching Demonstrates the Presence of Two Distinct Fluorophore Types Associated with NTIL Behavior in Pyrrolidone-Terminated PAMAM Dendrimers

Unique Property of Nontraditional Intrinsic Luminescence in the Transforming of Solution‐Hydrogel‐Solid and Its Applications

Osteogenic Differentiation of Human Mesenchymal Stem Cells by the Single Action of Luminescent Polyurea Oxide Biodendrimers

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