An activatable anticancer polymer-drug conjugate based on the self-immolative azobenzene motif

Taejun Eom, Wonjae Yoo, Yong Deok Lee, Jae Hyung Park, Youngson Choe, Joona Bang, Sehoon Kim, Anzar Khan

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Triggered cellular uptake of a synthetic graft copolymer carrying an anticancer drug is achieved through self-immolation of the side-chain azobenzene groups. In this concept, the conjugate is initially chemically neutral and does not possess cell-penetrating function. However, upon cleavage of the azobenzene moieties, a cascade process is initiated that ultimately reveals an ammonium cation in the vicinity of the polymer backbone. Hence, self-immolation results in the transformation of the neutral polymer chain into a polycation. This structural transformation allows the conjugate to be taken up by the cancer cells through favorable electrostatic interactions with the negatively charged phospholipid components of the cell membrane. Once inside the cells, the polymer releases covalently attached doxorubicin in a pristine form through a low pH activated release mechanism. The significance of this approach lies in the sensitivity of the azobenzene group to hypoxic conditions and to the enzyme azoreductase that is secreted by the microbial flora of the human colon and suggests a pathway to targeted drug delivery applications under these conditions.

Original languageEnglish
Pages (from-to)4574-4578
Number of pages5
JournalJournal of Materials Chemistry B
Volume5
Issue number24
DOIs
Publication statusPublished - 2017

Fingerprint

Azobenzene
Polymers
Pharmaceutical Preparations
Graft copolymers
Phospholipids
Cell membranes
Coulomb interactions
Static Electricity
Ammonium Compounds
Doxorubicin
Cations
Colon
Enzymes
Positive ions
Cells
Cell Membrane
Transplants
azobenzene
Neoplasms

ASJC Scopus subject areas

  • Chemistry(all)
  • Medicine(all)
  • Biomedical Engineering
  • Materials Science(all)

Cite this

An activatable anticancer polymer-drug conjugate based on the self-immolative azobenzene motif. / Eom, Taejun; Yoo, Wonjae; Lee, Yong Deok; Park, Jae Hyung; Choe, Youngson; Bang, Joona; Kim, Sehoon; Khan, Anzar.

In: Journal of Materials Chemistry B, Vol. 5, No. 24, 2017, p. 4574-4578.

Research output: Contribution to journalArticle

Eom, Taejun ; Yoo, Wonjae ; Lee, Yong Deok ; Park, Jae Hyung ; Choe, Youngson ; Bang, Joona ; Kim, Sehoon ; Khan, Anzar. / An activatable anticancer polymer-drug conjugate based on the self-immolative azobenzene motif. In: Journal of Materials Chemistry B. 2017 ; Vol. 5, No. 24. pp. 4574-4578.
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