Hyaluronic Acid Surface Modified Liposomes Prepared via
Orthogonal Aminoxy Coupling: Synthesis of Nontoxic
Aminoxylipids Based on Symmetrically alpha-Branched Fatty
Acids, Preparation of Liposomes by Microfluidic Mixing, and
Targeting to Cancer Cells Expressing CD44

J 2018

Hyaluronic Acid Surface Modified Liposomes Prepared via Orthogonal Aminoxy Coupling: Synthesis of Nontoxic Aminoxylipids Based on Symmetrically alpha-Branched Fatty Acids, Preparation of Liposomes by Microfluidic Mixing, and Targeting to Cancer Cells Expressing CD44

BARTHELDYOVA, E., R. EFFENBERG, J. MASEK, L. PROCHAZKA, P.T. KNOTIGOVA et. al.

Základní údaje

Originální název

Hyaluronic Acid Surface Modified Liposomes Prepared via Orthogonal Aminoxy Coupling: Synthesis of Nontoxic Aminoxylipids Based on Symmetrically alpha-Branched Fatty Acids, Preparation of Liposomes by Microfluidic Mixing, and Targeting to Cancer Cells Expressing CD44

Autoři

BARTHELDYOVA, E. (203 Česká republika), R. EFFENBERG (203 Česká republika), J. MASEK (203 Česká republika), L. PROCHAZKA (203 Česká republika), P.T. KNOTIGOVA (203 Česká republika), P. KULICH (203 Česká republika), F. HUBATKA (203 Česká republika), K. VELINSKA (203 Česká republika), J. ZELNICKOVA (203 Česká republika), D. ZOUHAROVA (203 Česká republika), M. FOJTIKOVA (203 Česká republika), Dominik HREBÍK (203 Česká republika, domácí), Pavel PLEVKA (203 Česká republika, garant, domácí), R. MIKULIK (203 Česká republika), A.D. MILLER (203 Česká republika), S. MACAULAY (826 Velká Británie a Severní Irsko), D. ZYKA (203 Česká republika), L. DROZ (203 Česká republika), M. RASKA (203 Česká republika), M. LEDVINA (203 Česká republika) a J. TURANEK (203 Česká republika)

Vydání

BIOCONJUGATE CHEMISTRY, WASHINGTON, AMER CHEMICAL SOC, 2018, 1043-1802

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10608 Biochemistry and molecular biology

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Impakt faktor

Impact factor: 4.349

Kód RIV

RIV/00216224:14740/18:00101017

Organizační jednotka

Středoevropský technologický institut

DOI

http://dx.doi.org/10.1021/acs.bioconjchem.8b00311

UT WoS

000439531800024

Klíčová slova anglicky

IN-VIVO; GENE DELIVERY; LIPOPHILIC DERIVATIVES; ADHESION MOLECULES; CATIONIC LIPIDS; OXIME LIGATION; DRUG-DELIVERY; RECEPTOR; VITRO; SIRNA

Štítky

rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 30. 4. 2019 08:52, Mgr. Pavla Foltynová, Ph.D.

Anotace

V originále

New synthetic aminoxy lipids are designed and synthesized as building blocks for the formulation of functionalized nanoliposomes by microfluidization using a NanoAssemblr. Orthogonal binding of hyaluronic acid onto the outer surface of functionalized nanoliposomes via aminoxy coupling (N-oxy ligation) is achieved at hemiacetal function of hyaluronic acid and the structure of hyaluronic acid-liposomes is visualized by transmission electron microscopy and cryotransmission electron microscopy. Observed structures are in a good correlation with data obtained by dynamic light scattering (size and (zeta-potential). In vitro experiments on cell lines expressing CD44 receptors demonstrate selective internalization of fluorochrome-labeled hyaluronic acid-liposomes, while cells with down regulated CD44 receptor levels exhibit very low internalization of hyaluronic acid-liposomes. A method based on microfluidization mixing was developed for preparation of monodispersive unilamellar liposomes containing aminoxy lipids and orthogonal binding of hyaluronic acid onto the liposomal surface was demonstrated. These hyaluronic acid-liposomes represent a potentially new drug delivery platform for CD44-targeted anticancer drugs as well as for immunotherapeutics and vaccines.

Návaznosti

GJ15-21631Y, projekt VaV

Název: Strukturní studie potenciálního protibakteriálního agens, fága 812K1-420 infikujícího zlatého stafylokoka

Investor: Grantová agentura ČR, Strukturní studie potenciálního protibakteriálního agens, fága 812K1-420 infikujícího zlatého stafylokoka

3041, interní kód MU

Název: Structural studies of human and animal pathogens from the order Picornavirales

Investor: EMBO (European Molecular Biology Organization), Structural studies of human and animal pathogens from the order Picornavirales

Citovat

BARTHELDYOVA, E., R. EFFENBERG, J. MASEK, L. PROCHAZKA, P.T. KNOTIGOVA, P. KULICH, F. HUBATKA, K. VELINSKA, J. ZELNICKOVA, D. ZOUHAROVA, M. FOJTIKOVA, Dominik HREBÍK, Pavel PLEVKA, R. MIKULIK, A.D. MILLER, S. MACAULAY, D. ZYKA, L. DROZ, M. RASKA, M. LEDVINA a J. TURANEK. Hyaluronic Acid Surface Modified Liposomes Prepared via Orthogonal Aminoxy Coupling: Synthesis of Nontoxic Aminoxylipids Based on Symmetrically alpha-Branched Fatty Acids, Preparation of Liposomes by Microfluidic Mixing, and Targeting to Cancer Cells Expressing CD44. BIOCONJUGATE CHEMISTRY. WASHINGTON: AMER CHEMICAL SOC, 2018, roč. 29, č. 7, s. 2343-2356. ISSN 1043-1802. Dostupné z: https://dx.doi.org/10.1021/acs.bioconjchem.8b00311.

@article{1421621,
   author = {Bartheldyova, E. and Effenberg, R. and Masek, J. and Prochazka, L. and Knotigova, P.T. and Kulich, P. and Hubatka, F. and Velinska, K. and Zelnickova, J. and Zouharova, D. and Fojtikova, M. and Hrebík, Dominik and Plevka, Pavel and Mikulik, R. and Miller, A.D. and Macaulay, S. and Zyka, D. and Droz, L. and Raska, M. and Ledvina, M. and Turanek, J.},
   article_location = {WASHINGTON},
   article_number = {7},
   doi = {http://dx.doi.org/10.1021/acs.bioconjchem.8b00311},
   keywords = {IN-VIVO; GENE DELIVERY; LIPOPHILIC DERIVATIVES; ADHESION MOLECULES; CATIONIC LIPIDS; OXIME LIGATION; DRUG-DELIVERY; RECEPTOR; VITRO; SIRNA},
   language = {eng},
   issn = {1043-1802},
   journal = {BIOCONJUGATE CHEMISTRY},
   title = {Hyaluronic Acid Surface Modified Liposomes Prepared via Orthogonal Aminoxy Coupling: Synthesis of Nontoxic Aminoxylipids Based on Symmetrically alpha-Branched Fatty Acids, Preparation of Liposomes by Microfluidic Mixing, and Targeting to Cancer Cells Expressing CD44},
   volume = {29},
   year = {2018}
}

TY  - JOUR
ID  - 1421621
AU  - Bartheldyova, E. - Effenberg, R. - Masek, J. - Prochazka, L. - Knotigova, P.T. - Kulich, P. - Hubatka, F. - Velinska, K. - Zelnickova, J. - Zouharova, D. - Fojtikova, M. - Hrebík, Dominik - Plevka, Pavel - Mikulik, R. - Miller, A.D. - Macaulay, S. - Zyka, D. - Droz, L. - Raska, M. - Ledvina, M. - Turanek, J.
PY  - 2018
TI  - Hyaluronic Acid Surface Modified Liposomes Prepared via Orthogonal Aminoxy Coupling: Synthesis of Nontoxic Aminoxylipids Based on Symmetrically alpha-Branched Fatty Acids, Preparation of Liposomes by Microfluidic Mixing, and Targeting to Cancer Cells Expressing CD44
JF  - BIOCONJUGATE CHEMISTRY
VL  - 29
IS  - 7
SP  - 2343-2356
EP  - 2343-2356
PB  - AMER CHEMICAL SOC
SN  - 10431802
KW  - IN-VIVO
KW  - GENE DELIVERY
KW  - LIPOPHILIC DERIVATIVES
KW  - ADHESION MOLECULES
KW  - CATIONIC LIPIDS
KW  - OXIME LIGATION
KW  - DRUG-DELIVERY
KW  - RECEPTOR
KW  - VITRO
KW  - SIRNA
N2  - New synthetic aminoxy lipids are designed and synthesized as building blocks for the formulation of functionalized nanoliposomes by microfluidization using a NanoAssemblr. Orthogonal binding of hyaluronic acid onto the outer surface of functionalized nanoliposomes via aminoxy coupling (N-oxy ligation) is achieved at hemiacetal function of hyaluronic acid and the structure of hyaluronic acid-liposomes is visualized by transmission electron microscopy and cryotransmission electron microscopy. Observed structures are in a good correlation with data obtained by dynamic light scattering (size and (zeta-potential). In vitro experiments on cell lines expressing CD44 receptors demonstrate selective internalization of fluorochrome-labeled hyaluronic acid-liposomes, while cells with down regulated CD44 receptor levels exhibit very low internalization of hyaluronic acid-liposomes. A method based on microfluidization mixing was developed for preparation of monodispersive unilamellar liposomes containing aminoxy lipids and orthogonal binding of hyaluronic acid onto the liposomal surface was demonstrated. These hyaluronic acid-liposomes represent a potentially new drug delivery platform for CD44-targeted anticancer drugs as well as for immunotherapeutics and vaccines.
ER  -

BARTHELDYOVA, E., R. EFFENBERG, J. MASEK, L. PROCHAZKA, P.T. KNOTIGOVA, P. KULICH, F. HUBATKA, K. VELINSKA, J. ZELNICKOVA, D. ZOUHAROVA, M. FOJTIKOVA, Dominik HREBÍK, Pavel PLEVKA, R. MIKULIK, A.D. MILLER, S. MACAULAY, D. ZYKA, L. DROZ, M. RASKA, M. LEDVINA a J. TURANEK. Hyaluronic Acid Surface Modified Liposomes Prepared via Orthogonal Aminoxy Coupling: Synthesis of Nontoxic Aminoxylipids Based on Symmetrically alpha-Branched Fatty Acids, Preparation of Liposomes by Microfluidic Mixing, and Targeting to Cancer Cells Expressing CD44. \textit{BIOCONJUGATE CHEMISTRY}. WASHINGTON: AMER CHEMICAL SOC, 2018, roč.~29, č.~7, s.~2343-2356. ISSN~1043-1802. Dostupné z: https://dx.doi.org/10.1021/acs.bioconjchem.8b00311.

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