Spectroscopic Investigations of Polyamido Amine Starburst Dendrimers Using the Solvatochromic Probe Phenol Blue

Richter-Egger, Dana; Landry, Jeff C.; Tesfai, and Aaron; Tucker, Sheryl A.

doi:10.1021/jp0100396

Cited by 46 publications

(71 citation statements)

References 78 publications

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“…21,[23][24][25] However, the results obtained for polymer-associated HONR indicate that this larger dye does not associate with the polymers in the same manner. For the dendritic PPI samples, absorption and fluorescence emission polarity measurements of polymer-associated HONR agree.…”

Section: Discussionmentioning

confidence: 94%

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Spectroscopic Characterization of Core-Based Hyperbranched Poly(ethyleneimine) and Dendritic Poly(propyleneimine) as Selective Uptake Devices

Kline

Tucker

2010

J. Phys. Chem. A

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Dendritic polymers have a wide range of potential applications; however, the extensive synthesis and limited availability of bulk quantities of dendrimers restrict their use. Core-based hyperbranched polymers (CBHPs) are, therefore, an attractive alternative to dendrimers for many applications. The selectivity of core-based hyperbranched poly(ethyleneimine), as a host for phenol blue and 2-hydroxy Nile red guests, was investigated using absorption and fluorescence spectroscopies. Research results are compared to those for its dendritic counterpart, poly(propyleneimine). Phenol blue is known to associate near the core in both the CBHPs and dendrimers investigated. The interfering agent, 2-hydroxy Nile red, has also been shown to associate with these polymers; however, this interaction occurs in the outermost branches. In this work, it was found that phenol blue was sequestered in both the CBHPs and dendrimers in the presence of interfering agent, and this association appeared to be the same as that of the polymers with phenol blue alone. Although the presence of 2-hydroxy Nile red did affect the association of phenol blue, there was still considerable association even when 2-hydroxy Nile red was in 10-fold excess. The association of phenol blue with both the CBHPs and dendrimers was stable and robust; however, the association of 2-hydroxy Nile red was relatively weak and unstable.

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Section: Discussionmentioning

confidence: 94%

“…21,23,24 Whereas previous work with PAMAM dendrimers utilized Nile red as an interfering agent, the low solubility of Nile red in aqueous solutions led to the use of a structural derivative, HONR.…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic Characterization of Core-Based Hyperbranched Poly(ethyleneimine) and Dendritic Poly(propyleneimine) as Selective Uptake Devices

Kline

Tucker

2010

J. Phys. Chem. A

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“…It has been reported that a PB probe can be well doped within the interior of PAMAM dendrimers but not on their surface (or periphery) and that the blue-shifted absorption band of PB encapsulated in PAMAM dendrimer indicates a less polar microenvironment inside the dendrimer. [13] Once fresh G4 PAMAM dendrimer was doped by PB guests, the mixing solution shows a visual color change from blue to purple, indicating a successful encapsulation. The UV-vis spectra (Figure 2) clearly reveal the blue-shifted absorption band of PB after 3 d. Meanwhile, PB emitted a red fluorescence at 570 nm upon excitation at 550 nm, whereas no fluorescence could be observed for an aqueous PB solution (without dendrimer).…”

Section: Resultsmentioning

confidence: 99%

“…1 H (300 MHz) and 13 C-NMR (75 MHz) spectra were performed by Jeol JNM-CMX300, and Fourier transform IR (FT-IR) spectra were recorded on Varian FT-60A/896. Elemental analysis was carried out by a PerkinElmer 2400 series II CHNS/O elemental analyzer.…”

Section: Instrumentsmentioning

confidence: 99%

Fluorescence Investigations of Oxygen‐Doped Simple Amine Compared with Fluorescent PAMAM Dendrimer

Chu

Imae

2009

Macromol. Rapid Commun.

126

104

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Blue emission of oxygen-doped tertiary amine (triethylamine), a key unit of fluorescent poly(amido amine) dendrimer, was demonstrated. It was found that the fluorescence intensity could be further enhanced if the tertiary amines locate densely in the dendrimer interior as the branching sites. Moreover, a solvatochromic phenol blue, instead of oxygen, is able to induce the blue fluorescence of the tertiary amino-branching sites based on a guaranteed host-guest complexation of phenol blue molecules and dendrimer interior.

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“…They found that the microenvironment polarity in the interior of these dendrimers is similar to 1-decanol. These authors also developed studies using the fluorescent, solvatochromic probe phenol blue in aqueous solutions [24], showing that the dye is associated inside the dendrimer and does not interact with the surface groups. Sideratou et al [25] investigated the solubilization and release properties of functionalized PEGylated diaminobutane poly (propylene imine) (DAB) dendrimers using pyrene as probe.…”

Section: Introductionmentioning

confidence: 99%

Solubilization and Release Properties of Dendrimers. Evaluation as Prospective Drug Delivery Systems

Fernández

González

Cerecetto

et al. 2006

Supramolecular Chemistry

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The polarity and accessibility to the interior of several dendrimers using phenanthrene, anthracene and tetrabenzonaphtalene as probe molecules have been investigated. In addition the prospective application of the dendrimers as drug carriers was evaluated by incorporating 5(6)-methylbenzo[1,2-c]1,2,5-oxadiazole N 1 -oxide] (1) and 2 0 -(benzo[1,2-c] 1,2,5-oxadiazol-5(6)-yl(N 1 -oxide) methylidene]-1-methoxy methane hydrazide (2). These compounds have antichagasic therapeutic activity but very low water solubility, which limits their application. Polypropylene imine dendrimers with amine terminal groups (DAB-16AT and DAB-32AT) and polyamide amine (PAMAM) dendrimers with carboxylate terminal groups (PAMAM-32CT), with amine terminal groups, (PAMAM-8AT and PAMAM-32AT) and with hydroxyl terminal groups (PAMAM-32OHT) were chosen for this study. Approximately one molecule of phenanthrene or anthracene was encapsulated in PAMAM-32CT, PAMAM-32AT, PAMAM-32OHT and DAB-32AT dendrimers. However, slight encapsulation was observed working with PAMAM-8AT and DAB-16AT. The studies with tetrabenzonaphtalene show that the guest molecule might only be partially caged within the dendrimer host. However, for relatively insoluble solutes the efficiency to encapsulate can be dictated by the saturation in the aqueous phase besides the dendrimer capacity to dissolve it. These dendrimers are also able to encapsulate and consequently solubilize 1 and 2 oxadiazol. However, PAMAM dendrimers are better for encapsulation and retention due to guest-host specific interactions. These interactions can be diminished by lowering the pH to allow a controlled deliverance of the drug.

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Spectroscopic Investigations of Polyamido Amine Starburst Dendrimers Using the Solvatochromic Probe Phenol Blue

Cited by 46 publications

References 78 publications

Spectroscopic Characterization of Core-Based Hyperbranched Poly(ethyleneimine) and Dendritic Poly(propyleneimine) as Selective Uptake Devices

Spectroscopic Characterization of Core-Based Hyperbranched Poly(ethyleneimine) and Dendritic Poly(propyleneimine) as Selective Uptake Devices

Fluorescence Investigations of Oxygen‐Doped Simple Amine Compared with Fluorescent PAMAM Dendrimer

Solubilization and Release Properties of Dendrimers. Evaluation as Prospective Drug Delivery Systems

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