Details
| Original language | English |
|---|---|
| Pages (from-to) | 2265-2270 |
| Number of pages | 6 |
| Journal | Chemistry - a European journal |
| Volume | 23 |
| Issue number | 10 |
| Publication status | Published - 16 Feb 2017 |
Abstract
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 (IC50=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.
Keywords
- ansamitocin, chemotherapy, Diels–Alder reaction, drug delivery, hyperthermia, nanoparticles
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
Sustainable Development Goals
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In: Chemistry - a European journal, Vol. 23, No. 10, 16.02.2017, p. 2265-2270.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - A Bio-Chemosynthetic Approach to Superparamagnetic Iron Oxide–Ansamitocin Conjugates for Use in Magnetic Drug Targeting
AU - Wang, Liang Liang
AU - Balakrishnan, Asha
AU - Bigall, Nadja Carola
AU - Candito, David
AU - Miethe, Jan Frederick
AU - Seidel, Katja
AU - Xie, Yu
AU - Ott, Michael
AU - Kirschning, Andreas
N1 - Publisher Copyright: © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Copyright: Copyright 2021 Elsevier B.V., All rights reserved.
PY - 2017/2/16
Y1 - 2017/2/16
N2 - 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 (IC50=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.
AB - 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 (IC50=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.
KW - ansamitocin
KW - chemotherapy
KW - Diels–Alder reaction
KW - drug delivery
KW - hyperthermia
KW - nanoparticles
UR - http://www.scopus.com/inward/record.url?scp=85013025274&partnerID=8YFLogxK
U2 - 10.1002/chem.201604903
DO - 10.1002/chem.201604903
M3 - Article
C2 - 27935144
AN - SCOPUS:85013025274
VL - 23
SP - 2265
EP - 2270
JO - Chemistry - a European journal
JF - Chemistry - a European journal
SN - 0947-6539
IS - 10
ER -