Exploring the influence of Diels–Alder linker length on photothermal molecule release from gold nanorods

Vetterlein, Claudia; Vásquez, Rodrigo A.; Acosta, Gerardo; Guzmán, Fanny; Alberício, Fernando; Célis, Freddy; Campos, Marcelo; Kogan, Marcelo J.; Araya, Eyleen

doi:10.1016/j.colsurfb.2018.03.021

Cited by 12 publications

(11 citation statements)

References 34 publications

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“…AuNPs are useful as a drug delivery system that allows to spatially and temporally control the release of drugs in the tumor to avoid unspecific effects. AuNPs can be conjugated to antitumor drugs and after external localized stimuli with a laser, it is possible to trigger the release of the drugs in the affected tissue due to the local photothermal effect [6,7,8,9].…”

Section: Introductionmentioning

confidence: 99%

Photothermally Controlled Methotrexate Release System Using β-Cyclodextrin and Gold Nanoparticles

et al. 2018

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The inclusion compound (IC) of cyclodextrin (CD) containing the antitumor drug Methotrexate (MTX) as a guest molecule was obtained to increase the solubility of MTX and decrease its inherent toxic effects in nonspecific cells. The IC was conjugated with gold nanoparticles (AuNPs), obtained by a chemical method, creating a ternary intelligent delivery system for MTX molecules, based on the plasmonic properties of the AuNPs. Irradiation of the ternary system, with a laser wavelength tunable with the corresponding surface plasmon of AuNPs, causes local energy dissipation, producing the controlled release of the guest from CD cavities. Finally, cell viability was evaluated using MTS assays for β-CD/MTX and AuNPs + β-CD/MTX samples, with and without irradiation, against HeLa tumor cells. The irradiated sample of the ternary system AuNPs + β-CD/MTX produced a diminution in cell viability attributed to the photothermal release of MTX.

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Section: Introductionmentioning

confidence: 99%

Photothermally Controlled Methotrexate Release System Using β-Cyclodextrin and Gold Nanoparticles

et al. 2018

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“…Supporting the choice of Diels-Alder chemistry is the fact that examples of this reaction have already been driven photothermally. Vetterlein et al (2018); Yamashita et al (2011);McElhanon and Wheeler (2001) However, this prior work was accomplished by directly tethering the reactive components near a photothermally active nanoparticle and, hence, the source of localized heat. It is unclear if photothermal heating would prove effective in driving this reaction in the dilute organic solution conditions that dominate traditional synthesis.…”

Section: Electronic Supplementary Materialsmentioning

confidence: 99%

“…An emerging approach is to use the photothermal effect of nanoscale systems to provide molecularscale heat, which has been shown to yield large enhancements to the rate of chemical transformations. Johnson et al (2015Johnson et al ( , 2018, Lear (2013, 2015), Fortenbaugh and Lear (2017), Burns and Lear (2019), Fasciani et al (2011), Goodman et al (2017), Vetterlein et al (2018), Yamashita et al (2011), Garnett et al (2012), Barsic et al (2007), Boyd et al (2006), Abadeer and Murphy (2016), Duncan et al (2010) To date, our group's efforts have focused on applications in materials, where we have demonstrated the utility of photothermal heating for driving both the decomposition Johnson et al (2015Johnson et al ( , 2018, Haas and Lear (2013) and formation Haas and Lear (2015), Fortenbaugh and Lear (2017), Burns and Lear (2019) of polymers, while other groups have shown that photothermal heating can be used to generate and manipulate inorganic materials. Garnett et al (2012), Barsic et al (2007), Boyd et al (2006) Beyond materials-based systems, photothermal heating has also been shown to be an effective driver of small molecule Fasciani et al (2011), Goodman et al (2017), Vetterlein et al (2018), Yamashita et al (2011) and biological Abadeer and Murphy (2016), Duncan et al (2010) transformations.…”

Section: Introductionmentioning

confidence: 99%

Nanoscale heat for organic transformations: a photothermally driven retro Diels–Alder reaction

Widstrom

Lear

2019

Appl Nanosci

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We demonstrate the ability of photothermal heating by hexanethiol-protected gold nanoparticles to drive a retro Diels-Alder reaction in an 8.47 mM 1,1,2,2-tetrachloroethane solution of the adduct formed between furan and maleic anhydride. We find that the presence of the thiol-based protecting ligands of the nanoparticle acts as an inhibitor of the retro Diels-Alder reaction for the adduct, which creates an avenue for greater control over the reaction behavior. However, even in the presence of these inhibiting ligands, photothermal heating provides an estimated 2.45 × 10 7 -fold enhancement of the instantaneous rate constant for this reaction, demonstrating the efficacy of photothermal heating in dilute organic solutions with ligandprotected particles.

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“…Research on nanomaterials has expanded in recent years for their use in drug delivery, imaging, therapy, diagnosis, and combined therapy, among other fields [ 1 , 2 , 3 , 4 , 5 ]. Organic, inorganic, biological-type, or hybrids between different structures have been proposed for diverse medical/biomedical applications [ 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 ]. Among the prospective materials for future applications, gold nanoparticles stand out, owing to their wide-ranging potential.…”

Section: Introductionmentioning

confidence: 99%

“…AuNPs have characteristic optical properties that are derived from their localized surface plasmon resonance (LSPR), allowing them to interact with light in a different way than bulk materials do [ 10 , 15 , 16 ]. The plasmon excitation has two main decay mechanisms: radiative and non-radiative, resulting in light scattering and absorption, respectively [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

Oligoarginine Peptide Conjugated to BSA Improves Cell Penetration of Gold Nanorods and Nanoprisms for Biomedical Applications

et al. 2021

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Gold nanoparticles (AuNPs) have been shown to be outstanding tools for drug delivery and biomedical applications, mainly owing to their colloidal stability, surface chemistry, and photothermal properties. The biocompatibility and stability of nanoparticles can be improved by capping the nanoparticles with endogenous proteins, such as albumin. Notably, protein coating of nanoparticles can interfere with and decrease their cell penetration. Therefore, in the present study, we functionalized albumin with the r8 peptide (All-D, octaarginine) and used it for coating NIR-plasmonic anisotropic gold nanoparticles. Gold nanoprisms (AuNPrs) and gold nanorods (AuNRs) were coated with bovine serum albumin (BSA) previously functionalized using a cell penetrating peptide (CPP) with the r8 sequence (BSA-r8). The effect of the coated and r8-functionalized AuNPs on HeLa cell viability was assessed by the MTS assay, showing a low effect on cell viability after BSA coating. Moreover, the internalization of the nanostructures into HeLa cells was assessed by confocal microscopy and transmission electron microscopy (TEM). As a result, both nanoconstructs showed an improved internalization level after being capped with BSA-r8, in contrast to the BSA-functionalized control, suggesting the predominant role of CPP functionalization in cell internalization. Thus, our results validate both novel nanoconstructs as potential candidates to be coated by endogenous proteins and functionalized with a CPP to optimize cell internalization. In a further approach, coating AuNPs with CPP-functionalized BSA can broaden the possibilities for biomedical applications by combining their optical properties, biocompatibility, and cell-penetration abilities.

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Exploring the influence of Diels–Alder linker length on photothermal molecule release from gold nanorods

Cited by 12 publications

References 34 publications

Photothermally Controlled Methotrexate Release System Using β-Cyclodextrin and Gold Nanoparticles

Photothermally Controlled Methotrexate Release System Using β-Cyclodextrin and Gold Nanoparticles

Nanoscale heat for organic transformations: a photothermally driven retro Diels–Alder reaction

Oligoarginine Peptide Conjugated to BSA Improves Cell Penetration of Gold Nanorods and Nanoprisms for Biomedical Applications

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