Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 17541-17551 |
| Seitenumfang | 11 |
| Fachzeitschrift | Chemistry - A European Journal |
| Jahrgang | 20 |
| Ausgabenummer | 52 |
| Publikationsstatus | Veröffentlicht - 24 Okt. 2014 |
Abstract
A combination of mutasynthesis, precursor-directed biosynthesis and semisynthesis provides access to new ansamitocin derivatives including new nanostructured particle-drug conjugates. These conjugates are based on the toxin ansamitocin and superparamagnetic iron oxide-silica core shell particles. New ansamitocin derivatives that are functionalized either with alkynylor azido groups in the ester side chain at C-3 are attached to nanostructured iron oxide core-silica shell particles. Upon exposure to an oscillating electromagnetic field these conjugates heat up and the ansamitocin derivatives are released by a retro-Diels-Alder reaction. For example, one ansamitocin derivative exerts strong antiproliferative activity against various cancer cell lines in the lower nanomolar range while the corresponding nanostructured particle-drug conjugate is not toxic. Therefore, these new conjugates can serve as dormant toxins that can be employed simultaneously in hyperthermia and chemotherapy when external inductive heating is applied.
ASJC Scopus Sachgebiete
- Chemische Verfahrenstechnik (insg.)
- Katalyse
- Chemie (insg.)
- Organische Chemie
Ziele für nachhaltige Entwicklung
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in: Chemistry - A European Journal, Jahrgang 20, Nr. 52, 24.10.2014, S. 17541-17551.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - Preparation of thermocleavable conjugates based on ansamitocin and superparamagnetic nanostructured particles by a chemobiosynthetic approach
AU - Mancuso, Lena
AU - Knobloch, Tobias
AU - Buchholz, Jessica
AU - Hartwig, Jan
AU - Möller, Lena
AU - Seidel, Katja
AU - Collisi, Wera
AU - Sasse, Florenz
AU - Kirschning, Andreas
PY - 2014/10/24
Y1 - 2014/10/24
N2 - A combination of mutasynthesis, precursor-directed biosynthesis and semisynthesis provides access to new ansamitocin derivatives including new nanostructured particle-drug conjugates. These conjugates are based on the toxin ansamitocin and superparamagnetic iron oxide-silica core shell particles. New ansamitocin derivatives that are functionalized either with alkynylor azido groups in the ester side chain at C-3 are attached to nanostructured iron oxide core-silica shell particles. Upon exposure to an oscillating electromagnetic field these conjugates heat up and the ansamitocin derivatives are released by a retro-Diels-Alder reaction. For example, one ansamitocin derivative exerts strong antiproliferative activity against various cancer cell lines in the lower nanomolar range while the corresponding nanostructured particle-drug conjugate is not toxic. Therefore, these new conjugates can serve as dormant toxins that can be employed simultaneously in hyperthermia and chemotherapy when external inductive heating is applied.
AB - A combination of mutasynthesis, precursor-directed biosynthesis and semisynthesis provides access to new ansamitocin derivatives including new nanostructured particle-drug conjugates. These conjugates are based on the toxin ansamitocin and superparamagnetic iron oxide-silica core shell particles. New ansamitocin derivatives that are functionalized either with alkynylor azido groups in the ester side chain at C-3 are attached to nanostructured iron oxide core-silica shell particles. Upon exposure to an oscillating electromagnetic field these conjugates heat up and the ansamitocin derivatives are released by a retro-Diels-Alder reaction. For example, one ansamitocin derivative exerts strong antiproliferative activity against various cancer cell lines in the lower nanomolar range while the corresponding nanostructured particle-drug conjugate is not toxic. Therefore, these new conjugates can serve as dormant toxins that can be employed simultaneously in hyperthermia and chemotherapy when external inductive heating is applied.
KW - Antitumor agents
KW - Hyperthermia
KW - Maytansinoids
KW - Mutasynthesis
KW - Nanoparticles
UR - http://www.scopus.com/inward/record.url?scp=84920154661&partnerID=8YFLogxK
U2 - 10.1002/chem.201404502
DO - 10.1002/chem.201404502
M3 - Article
C2 - 25418325
AN - SCOPUS:84920154661
VL - 20
SP - 17541
EP - 17551
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 52
ER -