Selective cytotoxicity of marine-derived fungal metabolite (3S,6S)-3,6-dibenzylpiperazine-2,5-dione against cancer cells adapted to nutrient starvation.
Antineoplastic Agents
/ chemistry
Aquatic Organisms
/ chemistry
Cell Line, Tumor
Cytotoxins
/ chemistry
Electron Transport
/ drug effects
Humans
Molecular Structure
Oxygen Consumption
/ drug effects
Paecilomyces
/ chemistry
Pancreatic Neoplasms
/ drug therapy
Piperazines
/ chemistry
Tumor Microenvironment
/ drug effects
Pancreatic Neoplasms
Journal
The Journal of antibiotics
ISSN: 1881-1469
Titre abrégé: J Antibiot (Tokyo)
Pays: England
ID NLM: 0151115
Informations de publication
Date de publication:
12 2020
12 2020
Historique:
received:
07
05
2020
accepted:
08
06
2020
revised:
28
05
2020
pubmed:
27
6
2020
medline:
20
2
2021
entrez:
27
6
2020
Statut:
ppublish
Résumé
The cancer cells that are adapted to the hypoxic and nutrient-starved conditions of the tumor microenvironment have become a key target for anticancer therapies. In the course of search for selective cytotoxic substances against cancer cells adapted to nutrient starvation, (3S,6S)-3,6-dibenzylpiperazine-2,5-dione (1) was isolated from culture extract of marine-derived Paecilomyces formous 17D47-2. Compound 1 showed cytotoxic activity on the human pancreatic carcinoma PANC-1 cells adapted to glucose-starved conditions with IC
Identifiants
pubmed: 32587348
doi: 10.1038/s41429-020-0340-3
pii: 10.1038/s41429-020-0340-3
doi:
Substances chimiques
Antineoplastic Agents
0
Cytotoxins
0
Piperazines
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
873-875Références
Rohwer N, Cramer T. Hypoxia-mediated drug resistance: novel insights on the functional interaction of HIFs and cell death pathways. Drug Resist Updat. 2011;14:191–201.
doi: 10.1016/j.drup.2011.03.001
pubmed: 21466972
Chen S, Rehman SK, Zhang W, Wen A, Yao L, Zhang J. Autophagy is a therapeutic target in anticancer drug resistance. Biochim Biophys Acta Rev Cancer. 2010;1806:220–9.
doi: 10.1016/j.bbcan.2010.07.003
Vaupel P, Kallinowski F, Okunieff P. Blood flow, oxygen and nutrient supply, and metabolic microenvironment of human tumors: a review. Cancer Res. 1989;49:6449–65.
pubmed: 2684393
Izuishi K, Kato K, Ogura T, Kinoshita T, Esumi H. Remarkable tolerance of tumor cells to nutrient deprivation: possible new biochemical target for cancer therapy. Cancer Res. 2000;60:6201–7.
pubmed: 11085546
Ueda J, Athikomkulchai S, Miyatake R, Saiki I, Esumi H, Awale S. (+)-Grandifloracin, an antiausterity agent, induces autophagic PANC-1 pancreatic cancer cell death. Drug Des Devel Ther. 2014;8:39–47.
pubmed: 24379655
Arai M, Shin D, Kamiya K, Ishida R, Setiawan A, Kotoku N, et al. Marine spongean polybrominated diphenyl ethers, selective growth inhibitors against the cancer cells adapted to glucose starvation, inhibits mitochondrial complex II. J Nat Med. 2017;71:44–9.
doi: 10.1007/s11418-016-1025-x
pubmed: 27449332
Arai M, Kamiya K, Shin D, Matsumoto H, Hisa T, Setiawan A, et al. N-Methylniphatyne A, a new 3-alkylpyridine alkaloid as an inhibitor of the cancer cells adapted to nutrient starvation, from an Indonesian marine sponge of Xestospongia sp. Chem Pharm Bull (Tokyo). 2016;64:766–71.
doi: 10.1248/cpb.c16-00118
Tang R, Kimishima A, Ishida R, Setiawan A, Arai M. Selective cytotoxicity of epidithiodiketopiperazine DC1149B, produced by marine-derived Trichoderma lixii on the cancer cells adapted to glucose starvation. J Nat Med. 2020;74:153–8.
doi: 10.1007/s11418-019-01357-w
pubmed: 31435860
Birkinshaw JH, Mohammed YS. Studies in the biochemistry of micro-organisms. 111. The production of L-phenylalanine anhydride (cis-L-3,6-dibenzyl-2,5-dioxopiperazine) by Penicillium nigricans (Bainier) Thom. Biochem J. 1962;85:523–7.
doi: 10.1042/bj0850523
pubmed: 13971138
pmcid: 1243775
Wang JM, Ding GZ, Fang L, Dai JG, Yu SS, Wang YH, et al. Thiodiketopiperazines produced by the endophytic fungus Epicoccum nigrum. J Nat Prod. 2010;73:1240–9.
doi: 10.1021/np1000895
pubmed: 20550196
Buttachon S, Ramos AA, Inácio Â, Dethoup T, Gales L, Lee M, et al. Bis-indolyl benzenoids, hydroxypyrrolidine derivatives and other constituents from cultures of the marine sponge-associated fungus Aspergillus candidus KUFA0062. Mar Drugs. 2018;16:119.
doi: 10.3390/md16040119
pmcid: 5923406
Momose I, Ohba S, Tatsuda D, Kawada M, Masuda T, Tsujiuchi G, et al. Mitochondrial inhibitors show preferential cytotoxicity to human pancreatic cancer PANC-1 cells under glucose-deprived conditions. Biochem Biophys Res Commun. 2010;392:460–6.
doi: 10.1016/j.bbrc.2010.01.050
pubmed: 20083087
Tang R, Kimishima A, Setiawan A, Arai M. Secalonic acid D as a selective cytotoxic substance on the cancer cells adapted to nutrient starvation. J Nat Med. 2020;74:495–500.
doi: 10.1007/s11418-020-01390-0
pubmed: 32002808
Weatherly LM, Shim J, Hashmi HN, Kennedy RH, Hess ST, Gosse JA. Antimicrobial agent triclosan is a proton ionophore uncoupler of mitochondria in living rat and human mast cells and in primary human keratinocytes. J Appl Toxicol. 2016;36:777–89.
doi: 10.1002/jat.3209
pubmed: 26204821
Molina JR, Sun Y, Protopopova M, Gera S, Bandi M, Bristow C, et al. An inhibitor of oxidative phosphorylation exploits cancer vulnerability. Nat Med. 2018;24:1036–46.
doi: 10.1038/s41591-018-0052-4
pubmed: 29892070
Fujioka R, Mochizuki N, Ikeda M, Sato A, Nomura S, Owada S, et al. Change in plasma lactate concentration during arctigenin administration in a phase I clinical trial in patients with gemcitabine-refractory pancreatic cancer. PLoS ONE. 2018;13:e0198219.
doi: 10.1371/journal.pone.0198219
pubmed: 29856804
pmcid: 5983509