Diethylene glycol ether-linked 3,4,5-trihydroxybenzamides as triply branched dendritic anchors to CdSe/ZnS core/shell type nanoparticles: potential hydrophilic fluorescent probes

Chen, Chien Tien; Pawar, Vijay D.; Munot, Yogesh S.; Chen, Chia Chun; Hsu, Chih Jung

doi:10.1039/b418806c

Cited by 21 publications

(10 citation statements)

References 25 publications

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“…Heteronanostructures have attracted significant attention in nanoscience research due to their exceptional properties and multi-functionality which cannot be realized by single component materials. [1][2][3][4][5][6][7][8] Among various types of heternanostructures, one-dimensional (1 D) polyaniline (PANI)-based nanocomposites are of great interest particularly in supercapacitors, 9 rechargeable batteries, [10][11][12] chemical sensors, [13][14][15] memory devices, 16 and optoelectronics. 17 Thus, various 1 D heteronanostructures containing PANI, such as PANI-coated carbon nanotubes, [11][12][13][18][19][20] Ni-coated PANI nanowires, 15 Au-coated PANI nanofibers, 16 PANI-decorated silver vanadium oxides nanowires, 10 Ag/PANI nanotubes, 21 and graphene oxide or reduced graphene/PANI composites, 9,14,[22][23][24][25][26][27] have been successfully synthesized.…”

Section: Introductionmentioning

confidence: 99%

Graphene/polyaniline nanorod arrays: synthesis and excellent electromagnetic absorption properties

et al. 2012

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In the paper, we find that graphene has a strong dielectric loss, but exhibits very weak attenuation properties to electromagnetic waves due to its high conductivity. As polyaniline nanorods are perpendicularly grown on the surface of graphene by an in situ polymerization process, the electromagnetic absorption properties of the nanocomposite are significantly enhanced. The maximum reflection loss reaches À45.1 dB with a thickness of the absorber of only 2.5 mm. Theoretical simulation in terms of the Cole-Cole dispersion law shows that the Debye relaxation processes in graphene/ polyaniline nanorod arrays are improved compared to polyaniline nanorods. The enhanced electromagnetic absorption properties are attributed to the unique structural characteristics and the charge transfer between graphene and polyaniline nanorods. Our results demonstrate that the deposition of other dielectric nanostructures on the surface of graphene sheets is an efficient way to fabricate lightweight materials for strong electromagnetic wave absorbents.

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Section: Introductionmentioning

confidence: 99%

Graphene/polyaniline nanorod arrays: synthesis and excellent electromagnetic absorption properties

et al. 2012

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“…All reaction products were isolated as chromatographically pure materials. The experimental procedures and analytical data for 1a and 1b have been reported previously [29].…”

Section: Methodsmentioning

confidence: 99%

“…[28] We have recently documented the first successful synthesis of water-soluble nanohybrids (i.e., 1a and 1b) between gallamide-based, tri-/penta-podal dendrons and CdSe/ZnS core/shell NPs as fluorescent probes. [29] The gallamide spacer serves as a dendritic template in extending single-podal site to tri-/penta-podal site multi-antennary probes. [30] Particularly in site-to-site carbohydrate-protein interactions, moderate affinity has been identified.…”

Section: Significance and Research Aimsmentioning

confidence: 99%

A Triantennary Dendritic Galactoside‐Capped Nanohybrid with a ZnS/CdSe Nanoparticle Core as a Hydrophilic, Fluorescent, Multivalent Probe for Metastatic Lung Cancer Cells

Chen

Munot

Salunke

et al. 2008

Adv Funct Materials

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A new tri‐antennary, galactoside‐capped gallamide dendritic anchor with thiolate focal group is synthesized via click chemistry. The highly hydrophilic dendron was efficiently anchored onto the surface of CdSe/ZnS core/shell nanoparticles in a covalent fashion, as evidenced by 1H NMR spectrum of the resultant nanohybrid with intact core fluorescent property. The water‐soluble nano‐hybrid was found smoothly and selectively uptaken by lung cancer cells enriched with membrane‐bound asialoprotein receptors in 2–3 h, as evidenced by confocal microscopic analysis. Furthermore, cancer cells that are undergoing active mitosis also tend to uptake the nanohybrids efficiently and remain sustainable in serum‐containing medium for several days, which shed light on its application as a photodynamic drug carrier for apoptosis study.

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“…S-Trityl-protected, tris-azide gallamide dendron 11 was synthesized from methyl gallate using a route that was described previously. 40 When catalyzed by CuSO 4 and sodium ascorbate in aqueous t-BuOH, propargyl ether 6 underwent cycloaddition with tris-azide dendron 11, furnishing triazoletethered, trivalent ligand 12 (Figures S11 and S12) in 90% yield (Scheme 4).…”

Section: ■ Introductionmentioning

confidence: 99%

Fluorescent Nanohybrids from ZnS/CdSe Quantum Dots Functionalized with Triantennary, N-Hydroxy-p-(4-arylbutanamido)benzamide/Gallamide Dendrons That Act as Inhibitors of Histone Deacetylase for Lung Cancer

Chen

Salunke

Wei

et al. 2021

ACS Appl. Bio Mater.

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N-Hydroxy-p-(4-arylbutanamido)benzamides (HABAB) belong to one class of histone deacetylase inhibitors (HDACi), which regulate deacetylation of lysine residue's amino group in histone, which results in chromatin constriction. In addition, transcriptional knockdown of the genetic loci possessing the suppressor genes of tumor occurs. A tripodal, HABAB-capped gallamide dendron possessing thiol anchoring unit was prepared by the click method. The resultant hydrophilic dendritic unit was easily attached on the outer layer of CdSe/ZnS (i.e., core/shell type) quantum dots by thiolate−Zn interaction, as supported via 1 H NMR spectroscopic analysis of the conjugate with its original property of fluorescence. The resulting, water-miscible nanohybrid (nano-HTPB) which bore trivalent, peripheral HABABs as the HDACi was efficiently taken up by cells of lung cancer and transported into the nuclei of cells in 3 h, as confirmed by confocal microscopy analysis. The concentration levels of 50% inhibition (IC 50 ) after 48 h incubation of the nano-HTPB for A549 and H1299 lung cancer cell lines were 14 and 18 nM, respectively, which were about 150-fold lower than those of the parent HTPB analogues. Nano-HTPB at 20 nM induced the knockdown of cell cycle at second growth/mitosis (i.e., G2/M) transition, which eventually led to apoptosis of lung cancer cells, demonstrating that the nano-HTPB was much more potent in inhibiting lung cancer cell growth in a synergistic manner than the parent HTPB analogues. In addition, the dendritic HABAB-capped nanohybrid, nano-HTPB, is more effective than the parent HTPB analogues both in vitro and in vivo. Furthermore, the nano-HTPB is more effective than the parent HTPB to increase the acetylation level of proteins related to histone and nonhistone like p53 and tubulin. Our results confirmed that covalent encapsulation of quantum dots with peripheral, triantennary HDACis represented a feasible strategy for synergistic drug delivery with enhanced biological effects.

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Diethylene glycol ether-linked 3,4,5-trihydroxybenzamides as triply branched dendritic anchors to CdSe/ZnS core/shell type nanoparticles: potential hydrophilic fluorescent probes

Abstract: Functionalized N-2-mercaptoethyl-gallamides bearing three or five hydroxyl units that are tethered with diethylene glycol ether(s) allow for transferring hydrophobically pyridine-capped CdSe/ZnS core/shell nanoparticles from an organic to an aqueous layer with intact fluorescent profiles.

Cited by 21 publications

References 25 publications

Graphene/polyaniline nanorod arrays: synthesis and excellent electromagnetic absorption properties

Graphene/polyaniline nanorod arrays: synthesis and excellent electromagnetic absorption properties

A Triantennary Dendritic Galactoside‐Capped Nanohybrid with a ZnS/CdSe Nanoparticle Core as a Hydrophilic, Fluorescent, Multivalent Probe for Metastatic Lung Cancer Cells

Fluorescent Nanohybrids from ZnS/CdSe Quantum Dots Functionalized with Triantennary, N-Hydroxy-p-(4-arylbutanamido)benzamide/Gallamide Dendrons That Act as Inhibitors of Histone Deacetylase for Lung Cancer

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