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Trichormamides C and D, antiproliferative cyclic lipopeptides from the cultured freshwater cyanobacterium cf. Oscillatoria sp. UIC 10045

[Display omitted] Extract from the cultured freshwater cf. Oscillatoria sp. UIC 10045 showed antiproliferative activity against HT-29 cell line. Bioassay-guided fractionation led to the isolation of two new cyclic lipopeptides, named trichormamides C (1) and D (2). The planar structures were determi...

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Published in:Bioorganic & medicinal chemistry 2015-07, Vol.23 (13), p.3153-3162
Main Authors: Luo, Shangwen, Kang, Hahk-Soo, Krunic, Aleksej, Chen, Wei-Lun, Yang, Jilai, Woodard, John L., Fuchs, James R., Hyun Cho, Sang, Franzblau, Scott G., Swanson, Steven M., Orjala, Jimmy
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cited_by cdi_FETCH-LOGICAL-c521t-1a7951dde4b83d6c8df126a6a8eae7ebbd43bf399f77c85881054744ef8f90563
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container_issue 13
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container_title Bioorganic & medicinal chemistry
container_volume 23
creator Luo, Shangwen
Kang, Hahk-Soo
Krunic, Aleksej
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Yang, Jilai
Woodard, John L.
Fuchs, James R.
Hyun Cho, Sang
Franzblau, Scott G.
Swanson, Steven M.
Orjala, Jimmy
description [Display omitted] Extract from the cultured freshwater cf. Oscillatoria sp. UIC 10045 showed antiproliferative activity against HT-29 cell line. Bioassay-guided fractionation led to the isolation of two new cyclic lipopeptides, named trichormamides C (1) and D (2). The planar structures were determined by combined analyses of HRESIMS, Q-TOF ESIMS/MS, and 1D and 2D NMR spectra. The absolute configurations of the amino acid residues were assigned by advanced Marfey’s analysis after partial and complete acid hydrolysis. Trichormamides C (1) is a cyclic undecapeptide and D (2) is a cyclic dodecapeptide, both containing a lipophilic β-aminodecanoic acid residue. Trichormamide C (1) displayed antiproliferative activities against HT-29 and MDA-MB-435 cancer cell lines with IC50 values of 1.7 and 1.0μM, respectively, as well as anti-Mycobacterium tuberculosis activity with MIC value of 23.8μg/mL (17.3μM). Trichormamide D (2) was found to be less potent against both HT-29 and MDA-MB-435 cancer cell lines with IC50 values of 11.5 and 11.7μM, respectively.
doi_str_mv 10.1016/j.bmc.2015.04.073
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The absolute configurations of the amino acid residues were assigned by advanced Marfey’s analysis after partial and complete acid hydrolysis. Trichormamides C (1) is a cyclic undecapeptide and D (2) is a cyclic dodecapeptide, both containing a lipophilic β-aminodecanoic acid residue. Trichormamide C (1) displayed antiproliferative activities against HT-29 and MDA-MB-435 cancer cell lines with IC50 values of 1.7 and 1.0μM, respectively, as well as anti-Mycobacterium tuberculosis activity with MIC value of 23.8μg/mL (17.3μM). 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Oscillatoria sp. UIC 10045</atitle><jtitle>Bioorganic &amp; medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2015-07-01</date><risdate>2015</risdate><volume>23</volume><issue>13</issue><spage>3153</spage><epage>3162</epage><pages>3153-3162</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>[Display omitted] Extract from the cultured freshwater cf. Oscillatoria sp. UIC 10045 showed antiproliferative activity against HT-29 cell line. Bioassay-guided fractionation led to the isolation of two new cyclic lipopeptides, named trichormamides C (1) and D (2). The planar structures were determined by combined analyses of HRESIMS, Q-TOF ESIMS/MS, and 1D and 2D NMR spectra. The absolute configurations of the amino acid residues were assigned by advanced Marfey’s analysis after partial and complete acid hydrolysis. Trichormamides C (1) is a cyclic undecapeptide and D (2) is a cyclic dodecapeptide, both containing a lipophilic β-aminodecanoic acid residue. 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identifier ISSN: 0968-0896
ispartof Bioorganic & medicinal chemistry, 2015-07, Vol.23 (13), p.3153-3162
issn 0968-0896
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language eng
recordid cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_4469202
source Elsevier
subjects Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - isolation & purification
Anti-Bacterial Agents - pharmacology
Antineoplastic Agents - chemistry
Antineoplastic Agents - isolation & purification
Antineoplastic Agents - pharmacology
Antiproliferative activity
Cell Line, Tumor
Cell Survival - drug effects
cf. Oscillatoria sp
Cyanobacteria
Cyanobacteria - chemistry
Cyclic lipopeptides
Drug Design
Drug Screening Assays, Antitumor
HT-29
HT29 Cells
Humans
Inhibitory Concentration 50
Lipopeptides - chemistry
Lipopeptides - isolation & purification
Lipopeptides - pharmacology
MDA-MB-435
Microbial Sensitivity Tests
Mycobacterium tuberculosis - drug effects
Mycobacterium tuberculosis - growth & development
Peptides, Cyclic - chemistry
Peptides, Cyclic - isolation & purification
Peptides, Cyclic - pharmacology
Structure-Activity Relationship
title Trichormamides C and D, antiproliferative cyclic lipopeptides from the cultured freshwater cyanobacterium cf. Oscillatoria sp. UIC 10045
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