Synthesis and evaluation of antimigratory and antiproliferative activities of lipid-linked [13]-macro-dilactones
The biological activities of a family of novel, lipid-linked 13-membered-ring macro-dilactones are reported. These [13]-macro-dilactones were synthesized by diacylation of functionalized diols, followed by ring-closing metathesis under conditions we had previously reported. Antimigratory, cytostatic...
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| Published in | Bioorganic & medicinal chemistry letters Vol. 20; no. 18; pp. 5472 - 5476 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Amsterdam
Elsevier Ltd
15.09.2010
Elsevier |
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| Abstract | The biological activities of a family of novel, lipid-linked 13-membered-ring macro-dilactones are reported. These [13]-macro-dilactones were synthesized by diacylation of functionalized diols, followed by ring-closing metathesis under conditions we had previously reported. Antimigratory, cytostatic and cytotoxic activities of the compounds against cancer cells were evaluated. Compound
13 was the most potent in the series, while compound
10 had the broadest concentration range of subtoxic antiproliferative activity. These compounds share common structural components, namely the [13]-macro-dilactone templated by an octyl α-glucoside 4,6-diol. |
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| AbstractList | The biological activities of a family of novel, lipid-linked 13-membered-ring macro-dilactones are reported. These [13]-macro-dilactones were synthesized by diacylation of functionalized diols, followed by ring-closing metathesis under conditions we had previously reported. Antimigratory, cytostatic and cytotoxic activities of the compounds against cancer cells were evaluated. Compound 13 was the most potent in the series, while compound 10 had the broadest concentration range of subtoxic antiproliferative activity. These compounds share common structural components, namely the [13]-macro-dilactone templated by an octyl alpha-glucoside 4,6-diol. The biological activities of a family of novel, lipid-linked 13-membered-ring macro-dilactones are reported. These [13]-macro-dilactones were synthesized by diacylation of functionalized diols, followed by ring-closing metathesis under conditions we had previously reported. Antimigratory, cytostatic and cytotoxic activities of the compounds against cancer cells were evaluated. Compound 13 was the most potent in the series, while compound 10 had the broadest concentration range of subtoxic antiproliferative activity. These compounds share common structural components, namely the [13]-macro-dilactone templated by an octyl α-glucoside 4,6-diol. The biological activities of a family of novel, lipid-linked 13-membered-ring macro-dilactones are reported. These [13]-macro-dilactones were synthesized by diacylation of functionalized diols, followed by ring-closing metathesis under conditions we had previously reported. Antimigratory, cytostatic and cytotoxic activities of the compounds against cancer cells were evaluated. Compound 13 was the most potent in the series, while compound 10 had the broadest concentration range of subtoxic antiproliferative activity. These compounds share common structural components, namely the [13]-macro-dilactone templated by an octyl α-glucoside 4,6-diol. The biological activities of a family of novel, lipid-linked 13-membered-ring macro-dilactones are reported. These [13]-macro-dilactones were synthesized by diacylation of functionalized diols, followed by ring-closing metathesis under conditions we had previously reported. Antimigratory, cytostatic and cytotoxic activities of the compounds against cancer cells were evaluated. Compound 13 was the most potent in the series, while compound 10 had the broadest concentration range of subtoxic antiproliferative activity. These compounds share common structural components, namely the [13]-macro-dilactone templated by an octyl a-glucoside 4,6-diol. |
| Author | Fenteany, Gabriel Peczuh, Mark W. Magpusao, Anniefer N. Desmond, Richard T. Billings, Katelyn J. |
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| CitedBy_id | crossref_primary_10_1021_jo400383g crossref_primary_10_1016_j_carres_2016_08_010 crossref_primary_10_1016_j_ccr_2012_02_015 crossref_primary_10_1016_j_bmc_2020_115671 crossref_primary_10_1002_chem_201300393 |
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| Keywords | Migrastatin Cell growth Octyl glucoside Inhibitors Cell migration Macro-dilactones Antineoplastic agent Human Aldose Glucoside Cytotoxicity Antimetastatic agent Oxygen heterocycle In vitro Macrolide Cell line Structure activity relation Bicyclic compound Glycoside Mammary gland Chemical synthesis Tumor cell |
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| SubjectTerms | Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Biological and medical sciences Cancer Cell growth Cell Line, Tumor Cell migration Cell Movement - drug effects Cell Proliferation - drug effects General aspects Glucosides - chemical synthesis Glucosides - chemistry Glucosides - pharmacology Humans Inhibitors Lactones - chemical synthesis Lactones - chemistry Lactones - pharmacology Lipids - chemistry Macro-dilactones Medical sciences Migrastatin Neoplasms - drug therapy Octyl glucoside Pharmacology. Drug treatments Structure-Activity Relationship |
| Title | Synthesis and evaluation of antimigratory and antiproliferative activities of lipid-linked [13]-macro-dilactones |
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