Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
Two new dimeric epipolythiodiketopiperazines, preussiadins A (1) and B (2), together with two known diastereomers, leptosins C (6) and A (7), were obtained from the mycelia of a Preussia typharum isolate. The structures of the new compounds were established by spectroscopic methods, and the absolute configurations of 1 and 2 were assigned by chemical transformations and comparisons of quantum chemical ECD and VCD calculations to experimental data. Compound 1 exhibited potent cytotoxic activity in the NCI-60 cell line panel with an average LC50 value of 251 nM. Further studies demonstrated that 1 circumvents P-glycoprotein-mediated drug resistance, yet had no significant antitumor activity in a xenograft UACC-62 melanoma model.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4073660 | PMC |
| http://dx.doi.org/10.1021/np5002253 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Strategies for total synthesis of bispyrrolidinoindoline alkaloids.
Nat Prod Rep
May 2022
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, and Yunnan University Library, Yunnan University, Kunming 650091, China.
Covering up to 2021Complex cyclotryptamine alkaloids with a bispyrrolidino[2,3-]indoline (BPI) skeleton are an intriguing family of natural products, exhibiting wide systematic occurrences, large structural diversity, and multiple biological activities. Based on their structural characteristics, BPI alkaloids can be classified into chimonanthine-type BPI alkaloids, BPI diketopiperazines, and BPI epipolythiodiketopiperazines. These intricate molecules have captivated great attention soon after their isolation and identification in the 1960s.
View Article and Find Full Text PDFFungal mycotoxin penisuloxazin A, a novel C-terminal Hsp90 inhibitor and characteristics of its analogues on Hsp90 function related to binding sites.
Biochem Pharmacol
December 2020
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, PR China; Laboratory for Marine Drugs and Bioproducts, Pilot National Laboratory for Marine Science and Technology, Qingdao 266237, PR China. Electronic address:
Hsp90 is a promising drug target for cancer therapy. However, toxicity and moderate effect are limitations of current inhibitors owing to broad protein degradation. The fungal mycotoxin penisuloxazin A (PNSA) belongs to a new epipolythiodiketopiperazines (ETPs) possessing a rare 3H-spiro[benzofuran-2,2'-piperazine] ring system.
View Article and Find Full Text PDFBiogenetically-inspired total synthesis of epidithiodiketopiperazines and related alkaloids.
Acc Chem Res
April 2015
‡Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
Natural products chemistry has historically been the prime arena for the discovery of new chemical transformations and the fountain of insights into key biological processes. It remains a fervent incubator of progress in the fields of chemistry and biology and an exchange mediating the flow of ideas between these allied fields of science. It is with this ethos that our group has taken an interest in and pursued the synthesis of a complex family of natural products termed the dimeric epipolythiodiketopiperazine (ETP) alkaloids.
View Article and Find Full Text PDFCytotoxic dimeric epipolythiodiketopiperazines from the ascomycetous fungus Preussia typharum.
J Nat Prod
June 2014
Natural Products Discovery Group, ‡Institute for Natural Products Applications and Research Technologies, and §Department of Chemistry and Biochemistry, Stephenson Life Sciences Research Center, 101 Stephenson Parkway, University of Oklahoma, Norman, Oklahoma 73019-5251, United States.
Two new dimeric epipolythiodiketopiperazines, preussiadins A (1) and B (2), together with two known diastereomers, leptosins C (6) and A (7), were obtained from the mycelia of a Preussia typharum isolate. The structures of the new compounds were established by spectroscopic methods, and the absolute configurations of 1 and 2 were assigned by chemical transformations and comparisons of quantum chemical ECD and VCD calculations to experimental data. Compound 1 exhibited potent cytotoxic activity in the NCI-60 cell line panel with an average LC50 value of 251 nM.
View Article and Find Full Text PDFSynthesis and Anticancer Activity of Epipolythiodiketopiperazine Alkaloids.
Chem Sci
April 2013
Massachusetts Institute of Technology, Department of Chemistry, Cambridge, Massachusetts 02139, USA.
The epipolythiodiketopiperazine (ETP) alkaloids are a highly complex class of natural products with potent anticancer activity. Herein, we report the application of a flexible and scalable synthesis, allowing the construction of dozens of ETP derivatives. The evaluation of these compounds against cancer cell lines in culture allows for the first expansive structure-activity relationship (SAR) to be defined for monomeric and dimeric ETP-containing natural products and their synthetic cognates.
View Article and Find Full Text PDF