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

Author(s)

Silva, Daniella Souza ^[1] ; Facchinatto, William Marcondes ^[2] ; Santos, Danilo Martins dos ^[3] ; Boni, Fernanda Isadora ^[4] ; Valdes, Talita Alvarenga ^[2] ; Leitao, Andrei ^[2] ; Gremiao, Maria Palmira Daflon ^[4] ; Colnago, Luiz Alberto ^[3] ; Campana-Filho, Sergio Paulo ^[2] ; Ribeiro, Sidney Jose Lima ^[1]

Affiliation

^[1] Sao Paulo State Univ, Inst Chem, Av Prof Francisco Degni 55, 237, BR-14800900 Araraquara, SP - Brazil

^[2] Univ Sao Paulo, Sao Carlos Inst Chem, Av Trabalhador Sao Carlense 400, 780, BR-13566590 Sao Carlos, SP - Brazil

^[3] Brazilian Corp Agr Res, Embrapa Instrumentat, Rua XV Novembro 1452, BR-13560970 Sao Carlos, SP - Brazil

^[4] Sao Paulo State Univ, Sch Pharmaceut Sci, Rod Araraquara Jau Km 01 S-N, BR-14800903 Araraquara, SP - Brazil

• Document type: Journal article
• Source: International Journal of Biological Macromolecules; v. 178, p. 558-568, MAY 1 2021.
• Web of Science Citations: 2

Abstract

Two samples of N-(2-hydroxy)-propyl-3-trimethylammonium, O-palmitoyl chitosan (DPCat) with different av-erage degrees of quaternization named as DPCat35 (DQ = 35%) and DPCat80 (DQ = 80%), were successfully syn-thesized by reacting glycidyltrimethylammonium chloride (GTMAC) with O-palmitoyl chitosan (DPCh) derivative (DS = 12%). Such amphiphilic derivatives of chitosan were fully water-soluble at 1.0 < pH < 12.0 and showed significant electrostatic stability enhancement of a self-assembly micellar nanostructure (100 \& ndash;320 nm) due to its positively-charged out-layer. In vitro mucoadhesive and cytotoxicity essays toward healthy fibroblast cells (Balb/C 3T3 clone A31 cell), human prostate cancer (DU145) and liver cancer (HepG2/ C3A) cell lines revealed that the biological properties of DPCat derivatives were strongly dependent on DQ. Ad-ditionally, DPCat35 had better interactions with the biological tissue and with mucin glycoproteins at pH 7.4 as well as exhibited potential to be used on the development of drug delivery systems for prostate and liver cancer treatment. (c) 2021 Elsevier B.V. All rights reserved. (AU)

• FAPESP's process: 16/20970-2 - Study of chitosan and hydrophilic derivatives by time domain NMR
• Grantee: William Marcondes Facchinatto
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 17/20973-4 - Coaxial electrospun nanofibers based on chitosan for controlled release of antibiotics and periodontic lesion treatment
• Grantee: Danilo Martins dos Santos
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• FAPESP's process: 19/13656-8 - Development and application of nuclear magnetic resonance in products and agricultural processes
• Grantee: Luiz Alberto Colnago
• Support Opportunities: Regular Research Grants