Reductive responsive hyaluronic acid conjugated S-nitrothiol prodrugs as drug carriers

Yin Ku Lin; Shiu Wei Wang; Ren Shen Lee

doi:10.1080/00914037.2021.1931207

Reductive responsive hyaluronic acid conjugated S-nitrothiol prodrugs as drug carriers

Yin Ku Lin, Shiu Wei Wang, Ren Shen Lee^*

^*Corresponding author for this work

Center for General Education

Research output: Contribution to journal › Journal Article › peer-review

1 Scopus citations

Abstract

S-nitroso-N-acetylpenicillamine (SNAP) and hydrophobic succinyl pyrene (SuPy) were conjugated to hyaluronic acid (HA) through cystamine dihydrochloride (Cys) linkers to synthesize NO-conjugated reductive–responsive prodrugs HA-Cys-(SNAP/SuPy). The prodrug could self-assemble into spherical micelles with a particle size of <200 nm. In a reductive environment (10 mM dithiothreitol, DTT), a substantial amount of the grafted NO was released, faster than that observed under physiological condition. Flow cytometry revealed that the uptake of HA-targeted DOX-encapsulated micelles was faster than that of free DOX. Microscopic analysis showed that NO-conjugated HA-Cys-(SNAP/SuPy) effectively generated NO within the cells and promoted the anticancer effect of DOX.

Original language	English
Pages (from-to)	932-945
Number of pages	14
Journal	International Journal of Polymeric Materials and Polymeric Biomaterials
Volume	71
Issue number	12
DOIs	https://doi.org/10.1080/00914037.2021.1931207
State	Published - 2022

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Publisher Copyright:
© 2021 Taylor & Francis Group, LLC.

Keywords

Hyaluronic acid
nitric oxide
prodrug
reductive–responsive
synergistic effect

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10.1080/00914037.2021.1931207

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title = "Reductive responsive hyaluronic acid conjugated S-nitrothiol prodrugs as drug carriers",

abstract = "S-nitroso-N-acetylpenicillamine (SNAP) and hydrophobic succinyl pyrene (SuPy) were conjugated to hyaluronic acid (HA) through cystamine dihydrochloride (Cys) linkers to synthesize NO-conjugated reductive–responsive prodrugs HA-Cys-(SNAP/SuPy). The prodrug could self-assemble into spherical micelles with a particle size of <200 nm. In a reductive environment (10 mM dithiothreitol, DTT), a substantial amount of the grafted NO was released, faster than that observed under physiological condition. Flow cytometry revealed that the uptake of HA-targeted DOX-encapsulated micelles was faster than that of free DOX. Microscopic analysis showed that NO-conjugated HA-Cys-(SNAP/SuPy) effectively generated NO within the cells and promoted the anticancer effect of DOX.",

keywords = "Hyaluronic acid, nitric oxide, prodrug, reductive–responsive, synergistic effect",

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year = "2022",

doi = "10.1080/00914037.2021.1931207",

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T1 - Reductive responsive hyaluronic acid conjugated S-nitrothiol prodrugs as drug carriers

AU - Lin, Yin Ku

AU - Wang, Shiu Wei

AU - Lee, Ren Shen

PY - 2022

Y1 - 2022

N2 - S-nitroso-N-acetylpenicillamine (SNAP) and hydrophobic succinyl pyrene (SuPy) were conjugated to hyaluronic acid (HA) through cystamine dihydrochloride (Cys) linkers to synthesize NO-conjugated reductive–responsive prodrugs HA-Cys-(SNAP/SuPy). The prodrug could self-assemble into spherical micelles with a particle size of <200 nm. In a reductive environment (10 mM dithiothreitol, DTT), a substantial amount of the grafted NO was released, faster than that observed under physiological condition. Flow cytometry revealed that the uptake of HA-targeted DOX-encapsulated micelles was faster than that of free DOX. Microscopic analysis showed that NO-conjugated HA-Cys-(SNAP/SuPy) effectively generated NO within the cells and promoted the anticancer effect of DOX.

AB - S-nitroso-N-acetylpenicillamine (SNAP) and hydrophobic succinyl pyrene (SuPy) were conjugated to hyaluronic acid (HA) through cystamine dihydrochloride (Cys) linkers to synthesize NO-conjugated reductive–responsive prodrugs HA-Cys-(SNAP/SuPy). The prodrug could self-assemble into spherical micelles with a particle size of <200 nm. In a reductive environment (10 mM dithiothreitol, DTT), a substantial amount of the grafted NO was released, faster than that observed under physiological condition. Flow cytometry revealed that the uptake of HA-targeted DOX-encapsulated micelles was faster than that of free DOX. Microscopic analysis showed that NO-conjugated HA-Cys-(SNAP/SuPy) effectively generated NO within the cells and promoted the anticancer effect of DOX.

KW - Hyaluronic acid

KW - nitric oxide

KW - prodrug

KW - reductive–responsive

KW - synergistic effect

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JO - International Journal of Polymeric Materials and Polymeric Biomaterials

JF - International Journal of Polymeric Materials and Polymeric Biomaterials

IS - 12

ER -

Reductive responsive hyaluronic acid conjugated S-nitrothiol prodrugs as drug carriers

Abstract

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Keywords

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