Supramolecular approach to obtain folate-functionalized nanoassociates

• Published in: Colloids and surfaces. A, Physicochemical and engineering aspects Vol. 702; p. 135060
• Main Authors: Gilmullina, Zuchra R., Morozova, Julia E., Syakaev, Victor V., Voloshina, Alexandra D., Lyubina, Anna P., Sapunova, Anastasia S., Shalaeva, Yana V., Ziganshina, Albina Yu, Antipin, Igor S.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 05.12.2024
• Subjects: Calixresorcinarene; Folic acid; In vitro PDT experiment; NMR FT-PGSE; Relative singlet oxygen quantum yield; Rhodamine B; Relative singlet oxygen quantum yield; NMR FT-PGSE; Calixresorcinarene; Rhodamine B; In vitro PDT experiment; Folic acid
• DOI: 10.1016/j.colsurfa.2024.135060
• ISSN: 0927-7757

Nanoassociates containing folic acid (FA) were obtained through solubilization by colloid solutions of three betaine calixresorcinarenes (sulfobetaine tetrapentylcalixresorcinarene С5-SB, hydroxysulfobetaine tetrapentyl- С5-hSB and tetraundecylcalixresorcinarene C11-hSB). FA was solubilized in its anionic form and fraction of bound molecules of FA was of from 89 % to 99 % (FT-PGSE NMR method data). The driving forces of FA encapsulation in the nanoassociates has been considered with the help of 1Н NMR, 2D NOESY NMR, and FT-PGSE NMR data. The macrocycle-FA nanoassociates have average hydrodynamic diameters of 3–5 nm (PDI of 0.1840.238) and a zeta potential close to zero; however, they were stable for 4–8 weeks. The enhancement of the internalization of the macrocycle-FA nanoassociates into M-HeLa cells compared to unloaded macrocycles self-associates was shown by the flow cytometry and fluorescence microscopy methods. Additionally, the growth of cytotoxicity of Rhodamine B by 19 % in the presence of С5-SB+FA nanoassociates compared to С5-SB self-associates in the in vitro PDT experiment on M-HeLa cells was found. Overall, the potential of a supramolecular approach to obtaining folate-functionalized nanocontainers has been demonstrated. [Display omitted] •Betaine amphiphilic calixresorcinarenes solubilize and bind FA in anionic form.•The efficiency of FA binding in macrocycles’ nanoassociates ranges from 89 % to 99 %.•Macrocycle-FA-RhB nanoassociates are toxic to M-HeLa cells under light irradiation.•FA introduction into macrocycle-RhB nanoassociates increases their toxicity up to 19 %.