N-(2-hydroxy)-propyl-3-trimethylammonium, O-palmitoyl chitosan: Synthesis, physicochemical and biological properties

Silva, Daniella Souza; Facchinatto, William Marcondes; Santos, Danilo Martins dos; Boni, Fernanda Isadora; Valdes, Talita Alvarenga; Leitão, Andrei; Gremião, Maria Palmira Daflon; Colnago, Luiz Alberto; Filho, Sérgio Paulo Campana; Ribeiro, Sidney José Lima

doi:10.1016/j.ijbiomac.2021.02.031

Cited by 16 publications

(16 citation statements)

References 61 publications

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“…The FT-IR spectrum of bPalm-CS-HTAP shows a strong signal at 1477 cm –1 , which is assigned to the C–H bending of −N + (CH 3 ) 3 ( Figure 3 D). 60 , 61 This evidence additionally confirmed the successful installation of HTAP units on the chitosan backbone.…”

Section: Resultssupporting

confidence: 61%

“…Aligned with the result obtained from 13 C solidstate NMR analysis of bPalm-CS, the DS bPalm of about 1.1% was calculated based on the relative ratio between the peak integration of H9′−H21′ and H25′−H37′ of bPalm units at The FT-IR spectrum of bPalm-CS-HTAP shows a strong signal at 1477 cm −1 , which is assigned to the C−H bending of −N + (CH 3 ) 3 (Figure 3D). 60,61 This evidence additionally confirmed the successful installation of HTAP units on the chitosan backbone. 2.2.…”

Section: Resultssupporting

confidence: 60%

“…Evidence of cell growth enhancement in the presence of bPalmCS-HTAP at low carrier concentrations could be explained by the inherent mucoadhesive property of chitosan, leading to cell attachment and proliferation to a greater extent. , However, when the concentration of bPalm-CS-HTAP increased, the permanent positive charge of the quaternary ammonium groups could result in excess electrostatic interactions with the plasma membrane of the cells, which cause aggregation of bPalm-CS-HTAP on the cell surfaces, thus impairing the cell membrane function and leading to cell death. ,,,, …”

Section: Resultsmentioning

confidence: 99%

“…The spectra were analyzed using the Topspin 3.6.1 software by Bruker BioSpin. The degree of substitution of bPalm units in bPalm-CS-HTAP was calculated using eq . ,,, where I H(palmitoyl) is the signal integral of H9′–H21′ and H25′–H37′ assigned to the bis-palmitoyl substituent in a range of 0.18–1.71 ppm, while I HTAP & CS is the signal integral of protons of the HTAP unit and the glucosamine ring from a signal in a range of 2.43–4.56 ppm. The degree of quaternization ( DQ ) of bPalm-CS-HTAP was calculated according to eq …”

Section: Methodsmentioning

confidence: 99%

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Amphiphilic Chitosan Bearing Double Palmitoyl Chains and Quaternary Ammonium Moieties as a Nanocarrier for Plasmid DNA

et al. 2022

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Amphiphilic chitosan, bPalm-CS-HTAP, having N -(2-((2,3-bis(palmitoyloxy)propyl)amino)-2-oxoethyl) (bPalm) groups as double hydrophobic tails and O -[(2-hydroxyl-3-trimethylammonium)] propyl (HTAP) groups as hydrophilic heads was synthesized and evaluated for its self-assembly properties and potential as a gene carrier. The degree of bis-palmitoyl group substitution ( DS bPalm ) and the degree of quaternization ( DQ ) were approximately 2 and 56%, respectively. bPalm-CS-HTAP was found to assemble into nanosized spherical particles with a hydrodynamic diameter ( D H ) of 265.5 ± 7.40 nm (PDI = 0.5) and a surface charge potential of 40.1 ± 0.04 mV. bPalm-CS-HTAP condensed the plasmid pVAX1.CoV2RBDme completely at a bPalm-CS-HTAP:pDNA ratio of 2:1. The self-assembled bPalm-CS-HTAP/pDNA complexes could enter HEK 293A and CHO cells and enabled gene expression at negligible cytotoxicity compared to commercial PEI (20 kDa). These results suggested that bPalm-CS-HTAP can be used as a promising nonviral gene carrier.

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Section: Resultssupporting

confidence: 61%

Section: Resultssupporting

confidence: 60%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Amphiphilic Chitosan Bearing Double Palmitoyl Chains and Quaternary Ammonium Moieties as a Nanocarrier for Plasmid DNA

et al. 2022

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“…Embora os valores de potencial  de quitosana sejam comumente associados à protonação das unidades GlcN, este não é o caso das amostras de quitina. De fato, como os valores de 𝐺𝐴 ̅̅̅̅ de beta-quitina e de whiskers são bastante elevados, há poucas unidades GlcN passíveis de protonação em meios ácidos (SILVA et al, 2021).…”

Section: Amostraunclassified

Produção e caracterização de >i<whiskers>/i< de beta-quitina por diferentes tratamentos ácidos e sua aplicação na remoção de corantes em meio aquoso

Habitzreuter¹

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Em primeiro lugar, gostaria de agradecer à minha esposa Indyara. Sem sua parceria, apoio, incentivo e puxões de orelha, este trabalho não seria concluído. Foi em sua companhia que vivi minhas maiores vitórias: superar uma depressão, redigir esta tese e a maior de todas -ser pai. Que nosso filho Dante possa se orgulhar dos pais que tem. Aproveito para agradecer a ele que, embora ainda não tenha nascido, foi peça fundamental na motivação para o término deste trabalho. Papai te ama! À minha família, pedra fundamental de tudo que tenho me tornado, pelo amor, incentivo e dedicação: minha mãe Márcia, que sempre me incentivou e acreditou em mim; meu pai Eulóquio que, embora tenha partido cedo demais ainda se faz presente diariamente em nossas vidas. Aos meus irmãos Mateus e Ester, por todos os momentos de descontração que, mesmo à distância, fizeram toda a diferença nesta trajetória. Aos meus avós Núfia e Antônio, tios Daniel e Maristela e primos Iuri e Igor, que fazem parte deste meu núcleo familiar tão incrível. Agradeço também aos meus cunhados Naiara e Bruno, bem como meus sogros Elenice e Enoc.Ao professor doutor Sérgio Paulo Campana Filho, pelas oportunidades tanto na pesquisa quanto no ensino, pela orientação e auxílios valorosos durante todo este período, mas sobretudo pela amizade, que não se limita às atividades de laboratório.Estendo meus agradecimentos à Regiane, sua esposa, que foi peça importante durante um dos momentos mais complicados de minha vida. O acolhimento foi fundamental durante este período.À professora doutora Elisabete Frollini, pela parceria e oportunidades que me foram abertas no Grupo de Materiais Macromoleculares e Fibras Lignocelulósicas.Ao professor doutor Daniel de Souza Corrêa, por ter aberto as portas da Embrapa Instrumentação para diversas análises.Aos amigos e colegas do Grupo de Físico-Química Orgânica e do Macromolignocell, que fizeram parte desta jornada:

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Palmitic acid‐ and cysteine‐functionalized nanoparticles overcome mucus and epithelial barrier for oral delivery of drug

Xie

Jin

et al. 2023

Bioengineering & Transla Med

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Nanoparticles (NPs) used for oral administration have greatly improved drug bioavailability and therapeutic efficacy. Nevertheless, NPs are limited by biological barriers, such as gastrointestinal degradation, mucus barrier, and epithelial barrier. To solve these problems, we developed the PA‐N‐2‐HACC‐Cys NPs loaded with anti‐inflammatory hydrophobic drug curcumin (CUR) (CUR@PA‐N‐2‐HACC‐Cys NPs) by self‐assembled amphiphilic polymer, composed of the N‐2‐Hydroxypropyl trimethyl ammonium chloride chitosan (N‐2‐HACC), hydrophobic palmitic acid (PA), and cysteine (Cys). After oral administration, the CUR@PA‐N‐2‐HACC‐Cys NPs had good stability and sustained release under gastrointestinal conditions, followed by adhering to the intestine to achieve drug mucosal delivery. Additionally, the NPs could penetrate mucus and epithelial barriers to promote cellular uptake. The CUR@PA‐N‐2‐HACC‐Cys NPs could open tight junctions between cells for transepithelial transport while striking a balance between mucus interaction and diffusion through mucus. Notably, the CUR@PA‐N‐2‐HACC‐Cys NPs improved the oral bioavailability of CUR, which remarkably relieved colitis symptoms and promoted mucosal epithelial repair. Our findings proved that the CUR@PA‐N‐2‐HACC‐Cys NPs had excellent biocompatibility, could overcome mucus and epithelial barriers, and had significant application prospects for oral delivery of the hydrophobic drugs.

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N-(2-hydroxy)-propyl-3-trimethylammonium, O-palmitoyl chitosan: Synthesis, physicochemical and biological properties

Cited by 16 publications

References 61 publications

Amphiphilic Chitosan Bearing Double Palmitoyl Chains and Quaternary Ammonium Moieties as a Nanocarrier for Plasmid DNA

Amphiphilic Chitosan Bearing Double Palmitoyl Chains and Quaternary Ammonium Moieties as a Nanocarrier for Plasmid DNA

Produção e caracterização de >i<whiskers>/i< de beta-quitina por diferentes tratamentos ácidos e sua aplicação na remoção de corantes em meio aquoso

Palmitic acid‐ and cysteine‐functionalized nanoparticles overcome mucus and epithelial barrier for oral delivery of drug

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