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A Bio‐Chemosynthetic Approach to Superparamagnetic Iron Oxide–Ansamitocin Conjugates for Use in Magnetic Drug Targeting
Author(s) -
Wang LiangLiang,
Balakrishnan Asha,
Bigall NadjaCarola,
Candito David,
Miethe Jan Frederick,
Seidel Katja,
Xie Yu,
Ott Michael,
Kirschning Andreas
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201604903
Subject(s) - superparamagnetism , chemosynthesis , drug , iron oxide , conjugate , nanotechnology , targeted drug delivery , chemistry , materials science , drug delivery , chemical engineering , metallurgy , biology , pharmacology , physics , engineering , mathematical analysis , mathematics , hydrothermal vent , magnetization , quantum mechanics , magnetic field , hydrothermal circulation
A combination of mutasynthesis using a mutant strain of A. pretiosum blocked in the biosynthesis of amino‐hydroxybenzoic acid (AHBA) and semisynthesis relying on a Stille cross‐coupling step provided access to new ansamitocin derivatives of which one was attached by a thermolabile linker to nanostructured iron oxide particles. When exposed to an oscillating electromagnetic field the resulting iron oxide/ansamitocin conjugate 19 heats up in an aqueous suspension and the ansamitocin derivative 16 is released by means of a retro‐Diels–Alder reaction. It exerts strong antiproliferative activity (IC 50 =4.8 ng mg −1 ) in mouse fibroblasts. These new types of conjugates have the potential for combating cancer through hyperthermia and chemotherapy using an electromagnetic external trigger.