Halloysite-Catalyzed Esterification of Bio-Mass Derived Acids

Hamdi, Jumanah; Diehl, Brooke N.; Kilgore, Kaylin; Lomenzo, Stacey A.; Trudell, Mark L.

doi:10.1021/acsomega.9b02870

Cited by 25 publications

(22 citation statements)

References 26 publications

(38 reference statements)

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“…In the first step of the DTX@HNT/Au-SORT preparation, HNTs were treated with acid and sonicated to activate the hydroxyl groups of the HNTs for subsequent reactions and to open the cavities [ 68 ]. Following the activation, HNTs were functionalized with 3-chloropropyl silane (CPS) to enable conjugation of the sortilin antibody, and to increase HNT hydrophobicity [ 69 ].…”

Section: Resultsmentioning

confidence: 99%

Plasmonic photothermal release of docetaxel by gold nanoparticles incorporated onto halloysite nanotubes with conjugated 2D8-E3 antibodies for selective cancer therapy

et al. 2021

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Background Applied nanomaterials in targeted drug delivery have received increased attention due to tangible advantages, including enhanced cell adhesion and internalization, controlled targeted release, convenient detection in the body, enhanced biodegradation, etc. Furthermore, conjugation of the biologically active ingredients with the drug-containing nanocarriers (nanobioconjugates) has realized impressive opportunities in targeted therapy. Among diverse nanostructures, halloysite nanotubes (NHTs) with a rolled multilayer structure offer great possibilities for drug encapsulation and controlled release. The presence of a strong hydrogen bond network between the rolled HNT layers enables the controlled release of the encapsulated drug molecules through the modulation of hydrogen bonding either in acidic conditions or at higher temperatures. The latter can be conveniently achieved through the photothermal effect via the incorporation of plasmonic nanoparticles. Results The developed nanotherapeutic integrated natural halloysite nanotubes (HNTs) as a carrier; gold nanoparticles (AuNPs) for selective release; docetaxel (DTX) as a cytotoxic anticancer agent; human IgG1 sortilin 2D8-E3 monoclonal antibody (SORT) for selective targeting; and 3-chloropropyltrimethoxysilane as a linker for antibody attachment that also enhances the hydrophobicity of DTX@HNT/Au-SORT and minimizes DTX leaching in body’s internal environment. HNTs efficiently store DTX at room temperature and release it at higher temperatures via disruption of interlayer hydrogen bonding. The role of the physical expansion and disruption of the interlayer hydrogen bonding in HNTs for the controlled DTX release has been studied by dynamic light scattering (DLS), electron microscopy (EM), and differential scanning calorimetry (DSC) at different pH conditions. HNT interlayer bond disruption has been confirmed to take place at a much lower temperature (44 °C) at low pH vs. 88 °C, at neutral pH thus enabling the effective drug release by DTX@HNT/Au-SORT through plasmonic photothermal therapy (PPTT) by light interaction with localized plasmon resonance (LSPR) of AuNPs incorporated into the HNT pores. Conclusions Selective ovarian tumor targeting was accomplished, demonstrating practical efficiency of the designed nanocomposite therapeutic, DTX@HNT/Au-SORT. The antitumor activity of DTX@HNT/Au-SORT (apoptosis of 90 ± 0.3%) was confirmed by in vitro experiments using a caov-4 (ATCC HTB76) cell line (sortilin expression > 70%) that was successfully targeted by the sortilin 2D8-E3 mAb, tagged on the DTX@HNT/Au. Graphic abstract

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Section: Resultsmentioning

confidence: 99%

Plasmonic photothermal release of docetaxel by gold nanoparticles incorporated onto halloysite nanotubes with conjugated 2D8-E3 antibodies for selective cancer therapy

et al. 2021

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“…Subsequently, raw HNTs were used in the esterification reaction between levulinic acid and methanol to afford methyl levulinate [122]. Different experimental conditions were considered to achieve the highest rate of conversion as reported in Table 4.…”

Section: Halloysite For Biodiesel Productionmentioning

confidence: 99%

Halloysite Nanotubes: Smart Nanomaterials in Catalysis

2022

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The use of clay minerals as catalyst is renowned since ancient times. Among the different clays used for catalytic purposes, halloysite nanotubes (HNTs) represent valuable resources for industrial applications. This special tubular clay possesses high stability and biocompatibility, resistance against organic solvents, and most importantly be available in large amounts at a low cost. Therefore, HNTs can be efficiently used as catalysts themselves or supports for metal nanoparticles in several catalytic processes. This review reports a comprehensive overview of the relevant advances in the use of halloysite in catalysis, focusing the attention on the last five years.

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“…As evident from Table 1, EL can be prepared in excellent yields from feedstock like LA, AGL, and FAL. [27,[71][72][73][74][75]78] Both homogeneous and heterogeneous catalysts have been very effective for esterification or alcoholysis reactions. The reactions generally require elevated temperature and excess ethanol.…”

Section: La To Levulinic Acid Esters (Laes)mentioning

confidence: 99%

Recent Advances in the Value Addition of Biomass‐Derived Levulinic Acid: A Review Focusing on its Chemical Reactivity Patterns

Dutta

Bhat

2021

ChemCatChem

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Levulinic acid (LA) is one of the most prominent biomass‐derived chemical building blocks that can be transformed into specialty chemicals like fuels, solvents, monomers for polymers, plasticizers, surfactants, agrochemicals, and pharmaceuticals. Over the past three decades, an enormous amount of research data have been acquired on the preparation and downstream value addition of LA, and these works have been reviewed. However, considering the astonishing number of publications appearing every year on LA derivatives, the periodical review of recent works focusing on unique aspects of chemistry must be undertaken to critically evaluate the achievements to date, reassess the challenges, and recognize new opportunities. This review discusses the chemical‐catalytic synthesis of various derivatives of LA by focusing on its functionalities and reactivity patterns. Recent literature on some crucial derivatives such as γ‐valerolactone, 4,4’‐diphenolic acid, and ethyl levulinate have been tabulated and discussed. The synthetic interconversion between various derivatives, mechanistic insights, critical analysis of the reaction parameters toward selective preparation of various derivatives, and their potential commercial applications have been elaborated using predominantly heterogeneous catalysts. A critical assessment of the relative advantages and shortcomings of the existing synthetic strategies for various derivatives of LA has been presented to enkindle fresh ideas.

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Halloysite-Catalyzed Esterification of Bio-Mass Derived Acids

Cited by 25 publications

References 26 publications

Plasmonic photothermal release of docetaxel by gold nanoparticles incorporated onto halloysite nanotubes with conjugated 2D8-E3 antibodies for selective cancer therapy

Plasmonic photothermal release of docetaxel by gold nanoparticles incorporated onto halloysite nanotubes with conjugated 2D8-E3 antibodies for selective cancer therapy

Halloysite Nanotubes: Smart Nanomaterials in Catalysis

Recent Advances in the Value Addition of Biomass‐Derived Levulinic Acid: A Review Focusing on its Chemical Reactivity Patterns

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