Large Scale Conversion of Trilobolide into the Payload of Mipsagargin: 8-O-(12-Aminododecanoyl)- 8-O-Debutanoylthapsigargin

Publikation: Bidrag til tidsskriftTidsskriftartikelfagfællebedømt

Standard

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.

I: Biomolecules, Bind 10, 1640, 2020.

Publikation: Bidrag til tidsskriftTidsskriftartikelfagfællebedømt

Harvard

Zimmermann, T, Drasar, P, Rempelova, S, Christensen, SB, Khripach, V & Jurasek, M 2020, 'Large Scale Conversion of Trilobolide into the Payload of Mipsagargin: 8-O-(12-Aminododecanoyl)- 8-O-Debutanoylthapsigargin', Biomolecules, bind 10, 1640. https://doi.org/10.3390/biom10121640

APA

Zimmermann, T., Drasar, P., Rempelova, S., Christensen, S. B., Khripach, V., & Jurasek, M. (2020). Large Scale Conversion of Trilobolide into the Payload of Mipsagargin: 8-O-(12-Aminododecanoyl)- 8-O-Debutanoylthapsigargin. Biomolecules, 10, [1640]. https://doi.org/10.3390/biom10121640

Vancouver

Zimmermann T, Drasar P, Rempelova S, Christensen SB, Khripach V, Jurasek M. Large Scale Conversion of Trilobolide into the Payload of Mipsagargin: 8-O-(12-Aminododecanoyl)- 8-O-Debutanoylthapsigargin. Biomolecules. 2020;10. 1640. https://doi.org/10.3390/biom10121640

Author

Zimmermann, Tomas ; Drasar, Pavel ; Rempelova, Silvie ; Christensen, Søren Brøgger ; Khripach, Vladimir ; Jurasek, Michal. / Large Scale Conversion of Trilobolide into the Payload of Mipsagargin: 8-O-(12-Aminododecanoyl)- 8-O-Debutanoylthapsigargin. I: Biomolecules. 2020 ; Bind 10.

Bibtex

@article{cdb91856d51a4b4cbf147f29eb4cce12,
title = "Large Scale Conversion of Trilobolide into the Payload of Mipsagargin: 8-O-(12-Aminododecanoyl)- 8-O-Debutanoylthapsigargin",
abstract = "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.",
keywords = "Faculty of Health and Medical Sciences, Naturstofkemi, Syntese, Laser trilobum",
author = "Tomas Zimmermann and Pavel Drasar and Silvie Rempelova and Christensen, {S{\o}ren Br{\o}gger} and Vladimir Khripach and Michal Jurasek",
year = "2020",
doi = "10.3390/biom10121640",
language = "English",
volume = "10",
journal = "Biomolecules",
issn = "2218-273X",
publisher = "MDPI",

}

RIS

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