Publication detail

N-Oxy lipid-based click chemistry for orthogonal coupling of mannan onto nanoliposomes prepared by microfluidic mixing: Synthesis of lipids, characterisation of mannan-coated nanoliposomes and in vitro stimulation of dendritic cells

Bartheldyova, E (Bartheldyova, Eliska)[ 1 ] Knotigova, PT (Knotigova, Pavlina Turanek)[ 1 ] Zachova, K (Zachova, Katerina)[ 2,3 ] Masek, J (Masek, Josef)[ 1 ] Kulich, P (Kulich, Pavel)[ 1 ] Effenberg, R (Effenberg, Roman)[ 4 ] Zyka, D (Zyka, Daniel)[ 5 ] Hubatka, F (Hubatka, Frantisek)[ 1 ] Kotoucek, J (Kotoucek, Jan)[ 1 ] Celechovska, H (Celechovska, Hana)[ 1 ] Hezova, R (Hezova, Renata)[ 1 ] Tomeckova, A (Tomeckova, Andrea)[ 1 ] Maskova, E (Maskova, Eliska)[ 1 ] Fojtikova, M (Foj

Original Title

N-Oxy lipid-based click chemistry for orthogonal coupling of mannan onto nanoliposomes prepared by microfluidic mixing: Synthesis of lipids, characterisation of mannan-coated nanoliposomes and in vitro stimulation of dendritic cells

Type

journal article in Web of Science

Language

English

Original Abstract

New synthetic aminooxy lipid was designed and synthesized as a building block for the formulation of functionalised nanoliposomes (presenting onto the outer surface of aminooxy groups) by microfluidic mixing. Orthogonal binding of cellular mannan (Candida glabrata (CCY 26-20-1) onto the outer surface of functionalised nanoliposomes was modified by orthogonal binding of reducing termini of mannans to oxime lipids via a click chemistry reaction based on aminooxy coupling (oxime ligation). The aminooxy lipid was proved as a suitable active component for preparation of functionalised nanoliposomes by the microfluidic mixing method performed with the instrument NanoAssemblr T. This "on-chip technology" can be easily scaled-up. The structure of mannan-liposomes was visualized by transmission and scanning electron microscopy, including immunogold staining of recombinant mannan receptor bound onto mannosylated-liposomes. The observed structures are in a good correlation with data obtained by DLS, NTA, and TPRS methods. In vitro experiments on human and mouse dendritic cells demonstrate selective internalisation of fluorochrome-labelled mannan-liposomes and their ability to stimulate DC comparable to lipopolysaccharide. We describe a potentially new drug delivery platform for mannan receptor-targeted antimicrobial drugs as well as for immunotherapeutics. Furthermore, the platform based on mannans bound orthogonally onto the surface of nanoliposomes represents a self-adjuvanted carrier for construction of liposome-based recombinant vaccines for both systemic and mucosal routes of administration.

Keywords

Click chemistry - oxime ligation; Microfluidic mixing; Dendritic cells; Mannosylated liposomes; Mannan; Drug delivery

Authors

Bartheldyova, E (Bartheldyova, Eliska)[ 1 ] ; Knotigova, PT (Knotigova, Pavlina Turanek)[ 1 ] ; Zachova, K (Zachova, Katerina)[ 2,3 ] ; Masek, J (Masek, Josef)[ 1 ] ; Kulich, P (Kulich, Pavel)[ 1 ] ; Effenberg, R (Effenberg, Roman)[ 4 ] ; Zyka, D (Zyka, Daniel)[ 5 ] ; Hubatka, F (Hubatka, Frantisek)[ 1 ] ; Kotoucek, J (Kotoucek, Jan)[ 1 ] ; Celechovska, H (Celechovska, Hana)[ 1 ] ; Hezova, R (Hezova, Renata)[ 1 ] ; Tomeckova, A (Tomeckova, Andrea)[ 1 ] ; Maskova, E (Maskova, Eliska)[ 1 ] ; Fojtikova, M (Foj

Released

1. 3. 2019

ISBN

0144-8617

Periodical

Carbohydrate Polymers

Year of study

vol. 207

Number

issue 8

State

United Kingdom of Great Britain and Northern Ireland

Pages from

521

Pages to

532

Pages count

11

URL

https://linkinghub.elsevier.com/retrieve/pii/S0144861718312852

BibTex

@article{BUT158864,
  author="Bartheldyova, E (Bartheldyova, Eliska)[ 1 ] and Knotigova, PT (Knotigova, Pavlina Turanek)[ 1 ] and Zachova, K (Zachova, Katerina)[ 2,3 ] and Masek, J (Masek, Josef)[ 1 ] and Kulich, P (Kulich, Pavel)[ 1 ] and Effenberg, R (Effenberg, Roman)[ 4 ] and Zyka, D (Zyka, Daniel)[ 5 ] and Hubatka, F (Hubatka, Frantisek)[ 1 ] and Kotoucek, J (Kotoucek, Jan)[ 1 ] and Celechovska, H (Celechovska, Hana)[ 1 ] and Hezova, R (Hezova, Renata)[ 1 ] and Tomeckova, A (Tomeckova, Andrea)[ 1 ] and Maskova, E (Maskova, Eliska)[ 1 ] and Fojtikova, M (Foj",
  title="N-Oxy lipid-based click chemistry for orthogonal coupling of mannan onto nanoliposomes prepared by microfluidic mixing: Synthesis of lipids, characterisation of mannan-coated nanoliposomes and in vitro stimulation of dendritic cells",
  journal="Carbohydrate Polymers",
  year="2019",
  volume="vol. 207",
  number="issue 8",
  pages="521--532",
  doi="10.1016/j.carbpol.2018.10.121",
  issn="0144-8617",
  url="https://linkinghub.elsevier.com/retrieve/pii/S0144861718312852"
}