Abstract
The combination of copper-free click chemistry with metabolic labeling offers new opportunities in drug delivery. The objective of this study was to determine whether cubosomes functionalized with azide or dibenzocyclooctyne (DBCO) groups are able to undergo copper-free click chemistry with a strained cyclooctyne or azide, respectively. Phytantriol-based cubosomes were functionalized using phospholipids bearing an azide or DBCO group. The modified cubosome dispersions were characterized using dynamic light scattering, cryo-TEM, and small-angle X-ray scattering. The efficiency of "clickability" was assessed by reacting the cubosomes with a complementary dye and determining bound and unbound dye via size exclusion chromatography. The clickable cubosomes reacted specifically and efficiently with a click-Cy5 dye with minor changes to the size, shape, and structure of the cubosomes. This indicates that cubosomes can retain their unique internal structure while participating in copper-free click chemistry. This proof of concept study paves the way for the use of copper-free click chemistry and metabolic labeling with cubosomes for targeted drug delivery and imaging.
| Original language | English |
|---|---|
| Pages (from-to) | 149-157 |
| Number of pages | 9 |
| Journal | Bioconjugate Chemistry |
| Volume | 29 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 17 Jan 2018 |
Cite this
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Clickable Cubosomes for Antibody-Free Drug Targeting and Imaging Applications. / Alcaraz, Nicolas; Liu, Qingtao; Hanssen, Eric; Johnston, Angus; Boyd, Ben J.
In: Bioconjugate Chemistry, Vol. 29, No. 1, 17.01.2018, p. 149-157.Research output: Contribution to journal › Article › Research › peer-review
TY - JOUR
T1 - Clickable Cubosomes for Antibody-Free Drug Targeting and Imaging Applications
AU - Alcaraz, Nicolas
AU - Liu, Qingtao
AU - Hanssen, Eric
AU - Johnston, Angus
AU - Boyd, Ben J.
PY - 2018/1/17
Y1 - 2018/1/17
N2 - The combination of copper-free click chemistry with metabolic labeling offers new opportunities in drug delivery. The objective of this study was to determine whether cubosomes functionalized with azide or dibenzocyclooctyne (DBCO) groups are able to undergo copper-free click chemistry with a strained cyclooctyne or azide, respectively. Phytantriol-based cubosomes were functionalized using phospholipids bearing an azide or DBCO group. The modified cubosome dispersions were characterized using dynamic light scattering, cryo-TEM, and small-angle X-ray scattering. The efficiency of "clickability" was assessed by reacting the cubosomes with a complementary dye and determining bound and unbound dye via size exclusion chromatography. The clickable cubosomes reacted specifically and efficiently with a click-Cy5 dye with minor changes to the size, shape, and structure of the cubosomes. This indicates that cubosomes can retain their unique internal structure while participating in copper-free click chemistry. This proof of concept study paves the way for the use of copper-free click chemistry and metabolic labeling with cubosomes for targeted drug delivery and imaging.
AB - The combination of copper-free click chemistry with metabolic labeling offers new opportunities in drug delivery. The objective of this study was to determine whether cubosomes functionalized with azide or dibenzocyclooctyne (DBCO) groups are able to undergo copper-free click chemistry with a strained cyclooctyne or azide, respectively. Phytantriol-based cubosomes were functionalized using phospholipids bearing an azide or DBCO group. The modified cubosome dispersions were characterized using dynamic light scattering, cryo-TEM, and small-angle X-ray scattering. The efficiency of "clickability" was assessed by reacting the cubosomes with a complementary dye and determining bound and unbound dye via size exclusion chromatography. The clickable cubosomes reacted specifically and efficiently with a click-Cy5 dye with minor changes to the size, shape, and structure of the cubosomes. This indicates that cubosomes can retain their unique internal structure while participating in copper-free click chemistry. This proof of concept study paves the way for the use of copper-free click chemistry and metabolic labeling with cubosomes for targeted drug delivery and imaging.
UR - http://www.scopus.com/inward/record.url?scp=85038590215&partnerID=8YFLogxK
U2 - 10.1021/acs.bioconjchem.7b00659
DO - 10.1021/acs.bioconjchem.7b00659
M3 - Article
VL - 29
SP - 149
EP - 157
JO - Bioconjugate Chemistry
JF - Bioconjugate Chemistry
SN - 1043-1802
IS - 1
ER -