Thioholgamides: Thioamide-Containing Cytotoxic RiPP Natural Products
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Thioholgamides : Thioamide-Containing Cytotoxic RiPP Natural Products. / Kjaerulff, Louise; Sikandar, Asfandyar; Zaburannyi, Nestor; Adam, Sebastian; Herrmann, Jennifer; Koehnke, Jesko; Müller, Rolf.
In: ACS chemical biology, Vol. 12, No. 11, 2017, p. 2837-2841.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Thioholgamides
T2 - Thioamide-Containing Cytotoxic RiPP Natural Products
AU - Kjaerulff, Louise
AU - Sikandar, Asfandyar
AU - Zaburannyi, Nestor
AU - Adam, Sebastian
AU - Herrmann, Jennifer
AU - Koehnke, Jesko
AU - Müller, Rolf
PY - 2017
Y1 - 2017
N2 - Thioviridamide is a structurally unique ribosomally synthesized and post-translationally modified peptide that contains several thioamide bonds and is active against a number of cancer cell lines. In the search for naturally occurring thioviridamide analogs, we employed genome mining that led to the identification of several related gene clusters. Chemical screening followed by cultivation and isolation yielded thioholgamides A and B, two new additions to the thioviridamide family with several amino acid substitutions, a different N-capping moiety, and with one less thioamide bond. Thioholgamides display improved cytotoxicity in the submicromolar range against a range of cell lines and an IC50 of 30 nM for thioholgamide A against HCT-116 cells. Herein, we report the isolation and structural elucidation of thioholgamides A and B, a proposed biosynthetic cluster for their production, and their bioactivities against a larger panel of microorganisms and cancer cell lines.
AB - Thioviridamide is a structurally unique ribosomally synthesized and post-translationally modified peptide that contains several thioamide bonds and is active against a number of cancer cell lines. In the search for naturally occurring thioviridamide analogs, we employed genome mining that led to the identification of several related gene clusters. Chemical screening followed by cultivation and isolation yielded thioholgamides A and B, two new additions to the thioviridamide family with several amino acid substitutions, a different N-capping moiety, and with one less thioamide bond. Thioholgamides display improved cytotoxicity in the submicromolar range against a range of cell lines and an IC50 of 30 nM for thioholgamide A against HCT-116 cells. Herein, we report the isolation and structural elucidation of thioholgamides A and B, a proposed biosynthetic cluster for their production, and their bioactivities against a larger panel of microorganisms and cancer cell lines.
U2 - 10.1021/acschembio.7b00676
DO - 10.1021/acschembio.7b00676
M3 - Journal article
C2 - 28981254
AN - SCOPUS:85034651970
VL - 12
SP - 2837
EP - 2841
JO - A C S Chemical Biology
JF - A C S Chemical Biology
SN - 1554-8929
IS - 11
ER -
ID: 192043679