An activatable theranostic for targeted cancer therapy and imaging

Sankarprasad Bhuniya, Sukhendu Maiti, Eun Joong Kim, Hyunseung Lee, Jonathan L. Sessler, Kwan Soo Hong, Jong Seung Kim

Research output: Contribution to journalArticlepeer-review

202 Citations (Scopus)


A new theranostic strategy is described. It is based on the use of an "all in one" prodrug, namely the biotinylated piperazine-rhodol conjugate 4 a. This conjugate, which incorporates the anticancer drug SN-38, undergoes self-immolative cleavage when exposed to biological thiols. This leads to the tumor-targeted release of the active SN-38 payload along with fluorophore 1 a. This release is made selective as the result of the biotin functionality. Fluorophore 1 a is 32-fold more fluorescent than prodrug 4 a. It permits the delivery and release of the SN-38 payload to be monitored easily in?vitro and in?vivo, as inferred from cell studies and ex?vivo analyses of mice xenografts derived from HeLa cells, respectively. Prodrug 4 a also displays anticancer activity in the HeLa cell murine xenograft tumor model. On the basis of these findings we suggest that the present strategy, which combines within a single agent the key functions of targeting, release, imaging, and treatment, may have a role to play in cancer diagnosis and therapy. All in one: A new theranostic prodrug was developed containing a biotinylated piperazine-rhodol conjugate linked to the drug SN-38 through a self-immolative disulfide spacer. When exposed to cellular thiols in cancer cells, it is able to release the active chemotherapeutic, SN38, along with a diagnostic fluorophore. This theranostic framework permits the targeted delivery, release of an active agent (SN-38), and its facile monitoring in vitro and in vivo.

Original languageEnglish
Pages (from-to)4469-4474
Number of pages6
JournalAngewandte Chemie - International Edition
Issue number17
Publication statusPublished - 2014 Apr 22


  • SN-38
  • biotin
  • cellular imaging
  • glutathione
  • theranostic

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry


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