Synthesis and antileukemic activities of C1–C10-modified parthenolide analogues

[Display omitted] Parthenolide (PTL) is a sesquiterpene lactone natural product with anti-proliferative activity to cancer cells. Selective eradication of leukemic stem cells (LSCs) over healthy hematopoietic stem cells (HSCs) by PTL has been demonstrated in previous studies, which suggests PTL and...

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Published inBioorganic & medicinal chemistry Vol. 23; no. 15; pp. 4737 - 4745
Main Authors Kempema, Aaron M., Widen, John C., Hexum, Joseph K., Andrews, Timothy E., Wang, Dan, Rathe, Susan K., Meece, Frederick A., Noble, Klara E., Sachs, Zohar, Largaespada, David A., Harki, Daniel A.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.08.2015
Elsevier
Subjects
Acute myeloid leukemia
Alkenes - chemistry
Animals
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Biochemistry & Molecular Biology
Bone Marrow Cells - cytology
Bone Marrow Cells - drug effects
Bone Marrow Cells - metabolism
Bone marrow toxicity
Cell Line, Tumor
Cell Survival - drug effects
Chemistry
Chemistry, Medicinal
Chemistry, Organic
Crystallography, X-Ray
Cyclopropanation
Drug Design
Drug Screening Assays, Antitumor
Humans
Leukemia, Myeloid, Acute - metabolism
Leukemia, Myeloid, Acute - mortality
Life Sciences & Biomedicine
Mice
Molecular Conformation
Neoplastic Stem Cells - drug effects
Neoplastic Stem Cells - metabolism
Parthenolide
Pharmacology & Pharmacy
Physical Sciences
Reactive Oxygen Species - metabolism
Science & Technology
Sesquiterpene lactone
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
Sesquiterpenes - pharmacology
PtO2
LogD
PTL
BM
AraC
MTS
IMDM
DMEM
CSC
FBS
SL
HSC
Bone marrow toxicity
Sesquiterpene lactone
LSC
DME
SFEM
AML
MelB
DOX
Cyclopropanation
MEM
HEPES
ROS
CTL
Parthenolide
Acute myeloid leukemia
DMAPT
CANCER-CELLS
STEM-CELLS
ACUTE MYELOID-LEUKEMIA
DRUG-RESISTANCE
ANTICANCER
AGENTS
SESQUITERPENE LACTONE PARTHENOLIDE
NF-KAPPA-B
DERIVATIVES
EXPRESSION
Online AccessGet full text

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Abstract [Display omitted] Parthenolide (PTL) is a sesquiterpene lactone natural product with anti-proliferative activity to cancer cells. Selective eradication of leukemic stem cells (LSCs) over healthy hematopoietic stem cells (HSCs) by PTL has been demonstrated in previous studies, which suggests PTL and related molecules may be useful for targeting LSCs. Eradication of LSCs is required for curative therapy. Chemical optimizations of PTL to improve potency and pharmacokinetic parameters have focused largely on the α-methylene-γ-butyrolactone, which is essential for activity. Conversely, we evaluated modifications to the C1–C10 olefin and benchmarked new inhibitors to PTL with respect to inhibitory potency across a panel of cancer cell lines, ability to target drug-resistant acute myeloid leukemia (AML) cells, efficacy for inhibiting clonal growth of AML cells, toxicity to healthy bone marrow cells, and efficiency for promoting intracellular reactive oxygen species (ROS) levels. Cyclopropane 4 was found to possess less toxicity to healthy bone marrow cells, enhanced potency for the induction of cellular ROS, and similar broad-spectrum anti-proliferative activity to cancer cells in comparison to PTL.
AbstractList [Display omitted] Parthenolide (PTL) is a sesquiterpene lactone natural product with anti-proliferative activity to cancer cells. Selective eradication of leukemic stem cells (LSCs) over healthy hematopoietic stem cells (HSCs) by PTL has been demonstrated in previous studies, which suggests PTL and related molecules may be useful for targeting LSCs. Eradication of LSCs is required for curative therapy. Chemical optimizations of PTL to improve potency and pharmacokinetic parameters have focused largely on the α-methylene-γ-butyrolactone, which is essential for activity. Conversely, we evaluated modifications to the C1–C10 olefin and benchmarked new inhibitors to PTL with respect to inhibitory potency across a panel of cancer cell lines, ability to target drug-resistant acute myeloid leukemia (AML) cells, efficacy for inhibiting clonal growth of AML cells, toxicity to healthy bone marrow cells, and efficiency for promoting intracellular reactive oxygen species (ROS) levels. Cyclopropane 4 was found to possess less toxicity to healthy bone marrow cells, enhanced potency for the induction of cellular ROS, and similar broad-spectrum anti-proliferative activity to cancer cells in comparison to PTL.
Parthenolide ( PTL ) is a sesquiterpene lactone natural product with anti-proliferative activity to cancer cells. Selective eradication of leukemic stem cells (LSCs) over healthy hematopoietic stem cells (HSCs) by PTL has been demonstrated in previous studies, which suggests PTL and related molecules may be useful for targeting LSCs. Eradication of LSCs is required for curative therapy. Chemical optimizations of PTL to improve potency and pharmacokinetic parameters have focused largely on the α-methylene-γ-butyrolactone, which is essential for activity. Conversely, we evaluated modifications to the C1-C10 olefin and benchmarked new inhibitors to PTL with respect to inhibitory potency across a panel of cancer cell lines, ability to target drug-resistant acute myeloid leukemia (AML) cells, efficacy for inhibiting clonal growth of AML cells, toxicity to healthy bone marrow cells, and efficiency for promoting intracellular reactive oxygen species (ROS) levels. Cyclopropane 4 was found to possess less toxicity to healthy bone marrow cells, enhanced potency for the induction of cellular ROS, and similar broad-spectrum anti-proliferative activity to cancer cells in comparison to PTL .
Parthenolide (PTL) is a sesquiterpene lactone natural product with anti-proliferative activity to cancer cells. Selective eradication of leukemic stem cells (LSCs) over healthy hematopoietic stem cells (HSCs) by PTL has been demonstrated in previous studies, which suggests PTL and related molecules may be useful for targeting LSCs. Eradication of LSCs is required for curative therapy. Chemical optimizations of PTL to improve potency and pharmacokinetic parameters have focused largely on the α-methylene-γ-butyrolactone, which is essential for activity. Conversely, we evaluated modifications to the C1-C10 olefin and benchmarked new inhibitors to PTL with respect to inhibitory potency across a panel of cancer cell lines, ability to target drug-resistant acute myeloid leukemia (AML) cells, efficacy for inhibiting clonal growth of AML cells, toxicity to healthy bone marrow cells, and efficiency for promoting intracellular reactive oxygen species (ROS) levels. Cyclopropane 4 was found to possess less toxicity to healthy bone marrow cells, enhanced potency for the induction of cellular ROS, and similar broad-spectrum anti-proliferative activity to cancer cells in comparison to PTL.
Parthenolide (PTL) is a sesquiterpene lactone natural product with anti-proliferative activity to cancer cells. Selective eradication of leukemic stem cells (LSCs) over healthy hematopoietic stem cells (HSCs) by PTL has been demonstrated in previous studies, which suggests PTL and related molecules may be useful for targeting LSCs. Eradication of LSCs is required for curative therapy. Chemical optimizations of PTL to improve potency and pharmacokinetic parameters have focused largely on the alpha-methylenec-gamma-butyrolactone, which is essential for activity. Conversely, we evaluated modifications to the C1-C10 olefin and benchmarked new inhibitors to PTL with respect to inhibitory potency across a panel of cancer cell lines, ability to target drug-resistant acute myeloid leukemia (AML) cells, efficacy for inhibiting clonal growth of AML cells, toxicity to healthy bone marrow cells, and efficiency for promoting intracellular reactive oxygen species (ROS) levels. Cyclopropane 4 was found to possess less toxicity to healthy bone marrow cells, enhanced potency for the induction of cellular ROS, and similar broad-spectrum antiproliferative activity to cancer cells in comparison to PTL. (C) 2015 Elsevier Ltd. All rights reserved.
Author Sachs, Zohar
Noble, Klara E.
Andrews, Timothy E.
Wang, Dan
Harki, Daniel A.
Widen, John C.
Hexum, Joseph K.
Largaespada, David A.
Meece, Frederick A.
Kempema, Aaron M.
Rathe, Susan K.
AuthorAffiliation b Masonic Cancer Center, University of Minnesota, Minneapolis, MN 55455, USA
d Department of Pediatrics, University of Minnesota, Minneapolis, MN 55455, USA
e Stem Cell Institute, University of Minnesota, Minneapolis, MN 55455, USA
c Division of Hematology, Oncology and Transplantation, University of Minnesota, Minneapolis, MN 55455, USA
a Department of Medicinal Chemistry, University of Minnesota, Minneapolis, MN 55455, USA
AuthorAffiliation_xml – name: a Department of Medicinal Chemistry, University of Minnesota, Minneapolis, MN 55455, USA
– name: d Department of Pediatrics, University of Minnesota, Minneapolis, MN 55455, USA
– name: c Division of Hematology, Oncology and Transplantation, University of Minnesota, Minneapolis, MN 55455, USA
– name: b Masonic Cancer Center, University of Minnesota, Minneapolis, MN 55455, USA
– name: e Stem Cell Institute, University of Minnesota, Minneapolis, MN 55455, USA
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  surname: Kempema
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  organization: Department of Medicinal Chemistry, University of Minnesota, Minneapolis, MN 55455, USA
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  organization: Department of Medicinal Chemistry, University of Minnesota, Minneapolis, MN 55455, USA
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  surname: Andrews
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  organization: Department of Medicinal Chemistry, University of Minnesota, Minneapolis, MN 55455, USA
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  surname: Wang
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  organization: Department of Medicinal Chemistry, University of Minnesota, Minneapolis, MN 55455, USA
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  surname: Rathe
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  organization: Masonic Cancer Center, University of Minnesota, Minneapolis, MN 55455, USA
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  surname: Meece
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  organization: Department of Medicinal Chemistry, University of Minnesota, Minneapolis, MN 55455, USA
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  givenname: Klara E.
  surname: Noble
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  organization: Division of Hematology, Oncology and Transplantation, Department of Medicine, University of Minnesota, Minneapolis, MN 55455, USA
– sequence: 9
  givenname: Zohar
  surname: Sachs
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  organization: Division of Hematology, Oncology and Transplantation, Department of Medicine, University of Minnesota, Minneapolis, MN 55455, USA
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  givenname: Daniel A.
  surname: Harki
  fullname: Harki, Daniel A.
  email: daharki@umn.edu
  organization: Department of Medicinal Chemistry, University of Minnesota, Minneapolis, MN 55455, USA
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Issue 15
Keywords PtO2
LogD
PTL
BM
AraC
MTS
IMDM
DMEM
CSC
FBS
SL
HSC
Bone marrow toxicity
Sesquiterpene lactone
LSC
DME
SFEM
AML
MelB
DOX
Cyclopropanation
MEM
HEPES
ROS
CTL
Parthenolide
Acute myeloid leukemia
DMAPT
CANCER-CELLS
STEM-CELLS
ACUTE MYELOID-LEUKEMIA
DRUG-RESISTANCE
ANTICANCER
AGENTS
SESQUITERPENE LACTONE PARTHENOLIDE
NF-KAPPA-B
DERIVATIVES
EXPRESSION
Language English
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Snippet [Display omitted] Parthenolide (PTL) is a sesquiterpene lactone natural product with anti-proliferative activity to cancer cells. Selective eradication of...
Parthenolide (PTL) is a sesquiterpene lactone natural product with anti-proliferative activity to cancer cells. Selective eradication of leukemic stem cells...
Parthenolide ( PTL ) is a sesquiterpene lactone natural product with anti-proliferative activity to cancer cells. Selective eradication of leukemic stem cells...
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StartPage 4737
SubjectTerms Acute myeloid leukemia
Alkenes - chemistry
Animals
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Biochemistry & Molecular Biology
Bone Marrow Cells - cytology
Bone Marrow Cells - drug effects
Bone Marrow Cells - metabolism
Bone marrow toxicity
Cell Line, Tumor
Cell Survival - drug effects
Chemistry
Chemistry, Medicinal
Chemistry, Organic
Crystallography, X-Ray
Cyclopropanation
Drug Design
Drug Screening Assays, Antitumor
Humans
Leukemia, Myeloid, Acute - metabolism
Leukemia, Myeloid, Acute - mortality
Life Sciences & Biomedicine
Mice
Molecular Conformation
Neoplastic Stem Cells - drug effects
Neoplastic Stem Cells - metabolism
Parthenolide
Pharmacology & Pharmacy
Physical Sciences
Reactive Oxygen Species - metabolism
Science & Technology
Sesquiterpene lactone
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
Sesquiterpenes - pharmacology
Title Synthesis and antileukemic activities of C1–C10-modified parthenolide analogues
URI https://dx.doi.org/10.1016/j.bmc.2015.05.037
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Volume 23
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