Functionalization of Carboxylated Lignin Nanoparticles for Targeted and pH-responsive Delivery of Anticancer Drugs

Figueiredo, Patrícia; Ferro, Cláudio Alexandre Rodrigues; Kemell, Marianna; Liu, Zehua; Kiriazis, Alexandros; Lintinen, Kalle; Florindo, Helena F.; Yli‐Kauhaluoma, Jari; Hirvonen, Jouni; Kostiainen, Mauri A.; Santos, Hélder A.

doi:10.2217/nnm-2017-0219

Cited by 109 publications

(85 citation statements)

References 57 publications

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“…All the IR absorption bands and respective type of vibration present on the lignin structure are detailed in Table S2 (Supporting Information). Apart from the typical bands present on both original and carboxylated lignin polymers, including the alcohol and phenol OH (3500–3100 cm −1 ), the carbonyl groups (1600 cm −1 ) and the aromatic structure (1427–1512 cm −1 ), all the carboxylated lignin polymers exhibited a stronger adsorption band at ≈1720 cm −1 than the original lignin . Stretching vibrations of CO, which derive from the carbonyl situated at β‐location that is also present in the original lignin polymer, can also contribute to this band.…”

Section: Resultsmentioning

confidence: 98%

“…Carboxylated lignin was synthesized in order to increase the amount of free carboxyl groups for further conjugation reactions with the targeting ligands. For this, the hydroxyl groups on the original softwood kraft lignin structure were reacted with succinic anhydride, with 4‐dimethylaminopyridine (DMAP) as a nucleophilic catalyst . To find a balance between the lignin carboxylation degree and the long‐term stability at physiological conditions, we tested different ratios of lignin:succinic anhydride for the reaction, as summarized in Table S1 (Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

“…Lignin NPs (LNPs) with different sizes and shapes have been prepared using different approaches, such as antisolvent precipitation, interfacial crosslinking, polymerization, solvent exchange and sonication . In addition to their application as reinforcing agents in nanocomposites, LNPs have been recently employed for drug delivery applications . Moreover, LNPs present functional groups that can be chemically modified, and consequently, increase their application potential …”

Section: Introductionmentioning

confidence: 99%

“…In addition to their application as reinforcing agents in nanocomposites, LNPs have been recently employed for drug delivery applications . Moreover, LNPs present functional groups that can be chemically modified, and consequently, increase their application potential …”

Section: Introductionmentioning

confidence: 99%

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Preparation and Characterization of Dentin Phosphophoryn‐Derived Peptide‐Functionalized Lignin Nanoparticles for Enhanced Cellular Uptake

Figueiredo

Sipponen

Lintinen

et al. 2019

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The surface modification of nanoparticles (NPs) using different ligands is a common strategy to increase NP−cell interactions. Here, dentin phosphophoryn‐derived peptide (DSS) lignin nanoparticles (LNPs) are prepared and characterized, the cellular internalization of the DSS‐functionalized LNPs (LNPs‐DSS) into three different cancer cell lines is evaluated, and their efficacy with the widely used iRGD peptide is compared. It is shown that controlled extent of carboxylation of lignin improves the stability at physiological conditions of LNPs formed upon solvent exchange. Functionalization with DSS and iRGD peptides maintains the spherical morphology and moderate polydispersity of LNPs. The LNPs exhibit good cytocompatibility when cultured with PC3‐MM2, MDA‐MB‐231, and A549 in the conventional 2D model and in the 3D cell spheroid morphology. Importantly, the 3D cell models reveal augmented internalization of peptide‐functionalized LNPs and improve antiproliferative effects when the LNPs are loaded with a cytotoxic compound. Overall, LNPs‐DSS show equal or even superior cellular internalization than the LNPs‐iRGD, suggesting that DSS can also be used to enhance the cellular uptake of NPs into different types of cells, and release different cargos intracellularly.

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Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Preparation and Characterization of Dentin Phosphophoryn‐Derived Peptide‐Functionalized Lignin Nanoparticles for Enhanced Cellular Uptake

Figueiredo

Sipponen

Lintinen

et al. 2019

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“…This allows for the incorporation of a wide range of labels, therapeutic compounds, and targeting vectors on their surface Figueiredo, Ferro, et al, 2017). This allows for the incorporation of a wide range of labels, therapeutic compounds, and targeting vectors on their surface Figueiredo, Ferro, et al, 2017).…”

Section: One Of the Most Important Characteristics Of Both Cnc And LImentioning

confidence: 99%

Systematic in vitro biocompatibility studies of multimodal cellulose nanocrystal and lignin nanoparticles

Imlimthan

Correia

Figueiredo

et al. 2019

J Biomedical Materials Res

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Natural biopolymer nanoparticles (NPs), including nanocrystalline cellulose (CNC) and lignin, have shown potential as scaffolds for targeted drug delivery systems due to their wide availability, cost-efficient preparation, and anticipated biocompatibility. As both CNC and lignin can potentially cause complications in cell viability assays because of their ability to scatter the emitted light and absorb the assay reagents, we investigated the response of bioluminescent (CellTiter-Glo ® ), colorimetric (MTT ® and AlamarBlue ® ), and fluorometric (LIVE/DEAD ® ) assays for the determination of the biocompatibility of the multimodal CNC and lignin constructs in murine RAW 264.7 macrophages and 4T1 breast adenocarcinoma cell lines. Here, we have developed multimodal CNC and lignin NPs harboring the radiometal chelator 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid and the fluorescent dye cyanine 5 for the investigation of nanomaterial biodistribution in vivo with nuclear and optical imaging, which were then used as the model CNC and lignin nanosystems in the cell viability assay comparison. CellTiter-Glo ® based on the detection of ATP-dependent luminescence in viable cells revealed to be the best assay for both nanoconstructs for its robust linear response to increasing NP concentration and lack of interference from either of the NP types. Both multimodal CNC and lignin NPs displayed low cytotoxicity and favorable interactions with the cell lines, suggesting that they are good candidates for nanosystem development for targeted drug delivery in breast cancer and for theranostic applications. Our results provide useful guidance for cell viability assay compatibility for CNC and lignin NPs and facilitate the future translation of the materials for in vivo applications.

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Lignin Nanoparticles: Synthesis and Application

2021

Nano‐Technological Intervention in Agricultural Productivity

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Functionalization of Carboxylated Lignin Nanoparticles for Targeted and pH-responsive Delivery of Anticancer Drugs

Abstract: The resulting CLNPs are promising candidates for anticancer therapy.

Cited by 109 publications

References 57 publications

Preparation and Characterization of Dentin Phosphophoryn‐Derived Peptide‐Functionalized Lignin Nanoparticles for Enhanced Cellular Uptake

Preparation and Characterization of Dentin Phosphophoryn‐Derived Peptide‐Functionalized Lignin Nanoparticles for Enhanced Cellular Uptake

Systematic in vitro biocompatibility studies of multimodal cellulose nanocrystal and lignin nanoparticles

Lignin Nanoparticles: Synthesis and Application

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