Replacing d‑Glucosamine with Its l‑Enantiomer in Glycosylated Antitumor Ether Lipids (GAELs) Retains Cytotoxic Effects against Epithelial Cancer Cells and Cancer Stem Cells

We describe metabolically inert l-glucosamine-based glycosylated antitumor ether lipids (L-GAELs) that retain the cytotoxic effects of the D-GAELs including the ability to kill BT-474 breast cancer stem cells (CSCs). When compared to adriamycin, cisplatin, and the anti-CSC agent salinomycin, L-GAELs...

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Bibliographic Details
Published inJournal of medicinal chemistry Vol. 60; no. 5; pp. 2142 - 2147
Main Authors Ogunsina, Makanjuola, Samadder, Pranati, Idowu, Temilolu, Arthur, Gilbert, Schweizer, Frank
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 09.03.2017
Amer Chemical Soc
Subjects
Chemistry, Medicinal
Epithelium - metabolism
Glucosamine - chemistry
Glycosylation
Humans
Life Sciences & Biomedicine
Neoplasms - metabolism
Neoplastic Stem Cells - metabolism
Neoplastic Stem Cells - pathology
Pharmacology & Pharmacy
Science & Technology
Stereoisomerism
RESISTANCE
COMPLEX
BEEF-LIVER
PATHWAY
GLYCEROLIPIDS
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Summary:We describe metabolically inert l-glucosamine-based glycosylated antitumor ether lipids (L-GAELs) that retain the cytotoxic effects of the D-GAELs including the ability to kill BT-474 breast cancer stem cells (CSCs). When compared to adriamycin, cisplatin, and the anti-CSC agent salinomycin, L-GAELs display superior activity to kill cancer stem cells (CSCs). Mode of action studies indicate that L-GAELs like the D-GAELs kill cells via an apoptosis-independent mechanism that was not due to membranolytic effects.
Bibliography:ObjectType-Article-1
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ISSN:0022-2623
1520-4804
DOI:10.1021/acs.jmedchem.6b01773