Chemical adaptor systems

Doron Shabat*, Roey J. Amir, Anna Gopin, Neta Pessah, Marina Shamis

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

"Chemical adaptor systems" are molecules used to link different functionalities, based on unique reactivity that allows controlled fragmentation. Two different mechanistic reactivities were used to prepare chemical adaptor systems. The first is based on a spontaneous intra-cyclization reaction to form a stable ring molecule. Cleavage of the trigger generates a free nucleophile, for example, an amine group, which undergoes intra-cyclization to release the target molecule from the handle part (e.g., a targeting antibody or a solid support for synthesis). The second applied reactivity is an elimination reaction, which is usually based on a quinone-methide-type rearrangement. Similarly, cleavage of the trigger generates a free phenol functionality, which can undergo a self-elimination reaction through a quinone-methide rearrangement to release the target molecule. The adaptor molecules have been applied in the field of drug delivery to release a drug from a targeting device and in the field of solid-phase synthesis to release a synthetic molecule from the solid support. A chemical adaptor molecule has also been used as a building unit to construct dendrimers with a triggered fragmentation.

Original languageEnglish
Pages (from-to)2626-2634
Number of pages9
JournalChemistry - A European Journal
Volume10
Issue number11
DOIs
StatePublished - 7 Jun 2004

Keywords

  • Dendrimers
  • Drug delivery
  • Enzymes
  • Prodrugs
  • Self-immolative dendrimers

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