Large Scale Conversion of Trilobolide into the Payload of Mipsagargin: 8-O-(12-Aminododecanoyl)- 8-O-Debutanoylthapsigargin
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Large Scale Conversion of Trilobolide into the Payload of Mipsagargin: 8-O-(12-Aminododecanoyl)- 8-O-Debutanoylthapsigargin. / Zimmermann, Tomas; Drasar, Pavel; Rempelova, Silvie; Christensen, Søren Brøgger; Khripach, Vladimir; Jurasek, Michal.
In: Biomolecules, Vol. 10, 1640, 2020.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Large Scale Conversion of Trilobolide into the Payload of Mipsagargin: 8-O-(12-Aminododecanoyl)- 8-O-Debutanoylthapsigargin
AU - Zimmermann, Tomas
AU - Drasar, Pavel
AU - Rempelova, Silvie
AU - Christensen, Søren Brøgger
AU - Khripach, Vladimir
AU - Jurasek, Michal
PY - 2020
Y1 - 2020
N2 - In spite of the impressing cytotoxicity of thapsigargin (Tg), this compound cannot be usedas a chemotherapeutic drug because of general toxicity, causing unacceptable side effects. Instead,a prodrug targeted towards tumors, mipsagargin, was brought into clinical trials. What substantiallyreduces the clinical potential is the limited access to Tg and its derivatives and cost-inefficient syntheseswith unacceptably low yields. Laser trilobum, which contains a structurally related sesquiterpenelactone, trilobolide (Tb), is successfully cultivated. Here, we report scalable isolation of Tb fromL. trilobum and a transformation of Tb to 8-O-(12-aminododecanoyl)-8-O-debutanoylthapsigarginin seven steps. The use of cultivated L. trilobum offers an unlimited source of the active principlein mipsagargin.
AB - In spite of the impressing cytotoxicity of thapsigargin (Tg), this compound cannot be usedas a chemotherapeutic drug because of general toxicity, causing unacceptable side effects. Instead,a prodrug targeted towards tumors, mipsagargin, was brought into clinical trials. What substantiallyreduces the clinical potential is the limited access to Tg and its derivatives and cost-inefficient syntheseswith unacceptably low yields. Laser trilobum, which contains a structurally related sesquiterpenelactone, trilobolide (Tb), is successfully cultivated. Here, we report scalable isolation of Tb fromL. trilobum and a transformation of Tb to 8-O-(12-aminododecanoyl)-8-O-debutanoylthapsigarginin seven steps. The use of cultivated L. trilobum offers an unlimited source of the active principlein mipsagargin.
KW - Faculty of Health and Medical Sciences
KW - Naturstofkemi
KW - Syntese
KW - Laser trilobum
U2 - 10.3390/biom10121640
DO - 10.3390/biom10121640
M3 - Journal article
C2 - 33291419
VL - 10
JO - Biomolecules
JF - Biomolecules
SN - 2218-273X
M1 - 1640
ER -
ID: 252604457