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Erschienen in: Journal of Natural Medicines 1/2017

23.07.2016 | Original Paper

Marine spongean polybrominated diphenyl ethers, selective growth inhibitors against the cancer cells adapted to glucose starvation, inhibits mitochondrial complex II

Erschienen in: Journal of Natural Medicines | Ausgabe 1/2017

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Abstract

In the course of search for selective growth inhibitors against the cancer cells adapted to nutrient starvation, two polybrominated diphenyl ethers, 3,4,5-tribromo-2-(2′,4′-dibromophenoxy)-phenol (1) and 3,5-dibromo-2-(2′,4′-dibromophenoxy)-phenol (2) were isolated from an Indonesian marine sponge of Dysidea sp. Compounds 1 and 2 showed the anti-proliferative activity against PANC-1 cells under glucose-starved conditions with IC50 values of 2.1 and 3.8 µM, respectively, whereas no growth inhibition was observed up to 30 µM in the general culture conditions. The further mechanistic analysis indicated that compound 1 might act mainly by inhibiting complex II in the mitochondrial electron transport chain.
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Literatur
1.
Zurück zum Zitat Vaupel P, Kallinowski F, Okunieff P (1989) Blood flow, oxygen and nutrient supply, and metabolic microenvironment of human tumors: a Review. Cancer Res 49:6449–6465PubMed Vaupel P, Kallinowski F, Okunieff P (1989) Blood flow, oxygen and nutrient supply, and metabolic microenvironment of human tumors: a Review. Cancer Res 49:6449–6465PubMed
2.
Zurück zum Zitat Rohwer N, Cramer T (2011) Hypoxia-mediated drug resistance: novel insights on the functional interaction of HIFs and cell death pathways. Drug Resist Updat 14:191–201CrossRefPubMed Rohwer N, Cramer T (2011) Hypoxia-mediated drug resistance: novel insights on the functional interaction of HIFs and cell death pathways. Drug Resist Updat 14:191–201CrossRefPubMed
3.
Zurück zum Zitat Chen S, Rehman SK, Zhang W, Wen A, Yao L, Zhang J (2010) Autophagy is a therapeutic target in anticancer drug resistance. Biochim Biophys Acta 1806:220–229PubMed Chen S, Rehman SK, Zhang W, Wen A, Yao L, Zhang J (2010) Autophagy is a therapeutic target in anticancer drug resistance. Biochim Biophys Acta 1806:220–229PubMed
4.
Zurück zum Zitat Arai M, Kawachi T, Kotoku N, Nakata C, Kamada H, Tsunoda S, Tsutsumi Y, Endo H, Inoue M, Sato H, Kobayashi M (2016) Furospinosulin-1, marine spongean furanosesterterpene, suppresses the growth of hypoxia-adapted cancer cells by binding to transcriptional regulators p54nrb and LEDGF/p75. ChemBioChem 17:181–189CrossRefPubMed Arai M, Kawachi T, Kotoku N, Nakata C, Kamada H, Tsunoda S, Tsutsumi Y, Endo H, Inoue M, Sato H, Kobayashi M (2016) Furospinosulin-1, marine spongean furanosesterterpene, suppresses the growth of hypoxia-adapted cancer cells by binding to transcriptional regulators p54nrb and LEDGF/p75. ChemBioChem 17:181–189CrossRefPubMed
5.
Zurück zum Zitat Sumii Y, Kotoku N, Fukuda A, Kawachi T, Arai M, Kobayashi M (2015) Structure-activity relationship and in vivo anti-tumor evaluations of dictyoceratin-A and -C, hypoxia-selective growth inhibitors from marine sponge. Mar Drugs 13:7419–7432CrossRefPubMedPubMedCentral Sumii Y, Kotoku N, Fukuda A, Kawachi T, Arai M, Kobayashi M (2015) Structure-activity relationship and in vivo anti-tumor evaluations of dictyoceratin-A and -C, hypoxia-selective growth inhibitors from marine sponge. Mar Drugs 13:7419–7432CrossRefPubMedPubMedCentral
6.
Zurück zum Zitat Lu J, Kunimoto S, Yamazaki Y, Kaminishi M, Esumi H (2004) Kigamicin D, a novel anticancer agent based on a new anti-austerity strategy targeting cancer cells’ tolerance to nutrient starvation. Cancer Sci 95:547–552CrossRefPubMed Lu J, Kunimoto S, Yamazaki Y, Kaminishi M, Esumi H (2004) Kigamicin D, a novel anticancer agent based on a new anti-austerity strategy targeting cancer cells’ tolerance to nutrient starvation. Cancer Sci 95:547–552CrossRefPubMed
7.
Zurück zum Zitat Arai M, Kamiya K, Shin D, Matsumoto H, Hisa T, Setiawan A, Kotoku N, Kobayashi M (2016) 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 64:766–771 Arai M, Kamiya K, Shin D, Matsumoto H, Hisa T, Setiawan A, Kotoku N, Kobayashi M (2016) 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 64:766–771
8.
Zurück zum Zitat Fu X, Schmitz FJ (1996) New brominated diphenyl ether from an unidentified species of Dysidea sponge. 13C NMR Data for some brominated diphenyl ethers. J Nat Prod 59:1102–1103CrossRefPubMed Fu X, Schmitz FJ (1996) New brominated diphenyl ether from an unidentified species of Dysidea sponge. 13C NMR Data for some brominated diphenyl ethers. J Nat Prod 59:1102–1103CrossRefPubMed
9.
Zurück zum Zitat Capon R, Ghisalberti EL, Jefferies PR, Skelton BW, White AH (1981) Structural studies of halogenated diphenyl ethers from a marine sponge. J Chem Soc Perkin Trans 1:2464–2467CrossRef Capon R, Ghisalberti EL, Jefferies PR, Skelton BW, White AH (1981) Structural studies of halogenated diphenyl ethers from a marine sponge. J Chem Soc Perkin Trans 1:2464–2467CrossRef
10.
Zurück zum Zitat Momose I, Ohba S, Tatsuda D, Kawada M, Masuda T, Tsujiuchi G, Yamori T, Esumi H, Ikeda D (2010) Mitochondrial inhibitors show preferential cytotoxicity to human pancreatic cancer PANC-1 cells under glucose-deprived conditions. Biochem Biophys Res Commun 392:460–466CrossRefPubMed Momose I, Ohba S, Tatsuda D, Kawada M, Masuda T, Tsujiuchi G, Yamori T, Esumi H, Ikeda D (2010) Mitochondrial inhibitors show preferential cytotoxicity to human pancreatic cancer PANC-1 cells under glucose-deprived conditions. Biochem Biophys Res Commun 392:460–466CrossRefPubMed
11.
Zurück zum Zitat Carte B, Faulkner DJ (1981) Polybrominated diphenyl ethers from Dysidea herbacea, Dysidea chlorea and Phyllospongia foliascens. Tetrahedron 37:2335–2339CrossRef Carte B, Faulkner DJ (1981) Polybrominated diphenyl ethers from Dysidea herbacea, Dysidea chlorea and Phyllospongia foliascens. Tetrahedron 37:2335–2339CrossRef
12.
Zurück zum Zitat Fu X, Schmitz FJ, Govindan M, Abbas SA, Hanson KM, Horton PA, Crews P, Laney M, Schatzman RC (1995) Enzyme inhibitors: new and known polybrominated phenols and diphenyl ethers from four Indo-Pacific Dysidea sponges. J Nat Prod 58:1384–1391CrossRefPubMed Fu X, Schmitz FJ, Govindan M, Abbas SA, Hanson KM, Horton PA, Crews P, Laney M, Schatzman RC (1995) Enzyme inhibitors: new and known polybrominated phenols and diphenyl ethers from four Indo-Pacific Dysidea sponges. J Nat Prod 58:1384–1391CrossRefPubMed
13.
Zurück zum Zitat Handayani D, Edrada RA, Proksch P, Wray V, Witte L, van Soest RWM, Kunzmann A, Soedarsono (1997) Four new bioactive polybrominated diphenyl ethers of the sponge Dysidea herbacea from West Sumatra, Indonesia. J Nat Prod 60:1313–1316CrossRefPubMed Handayani D, Edrada RA, Proksch P, Wray V, Witte L, van Soest RWM, Kunzmann A, Soedarsono (1997) Four new bioactive polybrominated diphenyl ethers of the sponge Dysidea herbacea from West Sumatra, Indonesia. J Nat Prod 60:1313–1316CrossRefPubMed
14.
Zurück zum Zitat Unson MD, Holland ND, Faulkner DJ (1994) A brominated secondary metabolite synthesized by the cyanobacterial symbiont of a marine sponge and accumulation of the crystalline metabolite in the sponge tissue. Mar Biol 119:1–11CrossRef Unson MD, Holland ND, Faulkner DJ (1994) A brominated secondary metabolite synthesized by the cyanobacterial symbiont of a marine sponge and accumulation of the crystalline metabolite in the sponge tissue. Mar Biol 119:1–11CrossRef
15.
Zurück zum Zitat Hanif N, Tanaka J, Setiawan A, Trianto A, de Voogd NJ, Murni A, Tanaka C, Higa T (2007) Polybrominated diphenyl ethers from the Indonesian sponge Lamellodysidea herbacea. J Nat Prod 70:432–435CrossRefPubMed Hanif N, Tanaka J, Setiawan A, Trianto A, de Voogd NJ, Murni A, Tanaka C, Higa T (2007) Polybrominated diphenyl ethers from the Indonesian sponge Lamellodysidea herbacea. J Nat Prod 70:432–435CrossRefPubMed
16.
Zurück zum Zitat Sun S, Canning CB, Bhargava K, Sun X, Zhu W, Zhou N, Zhang Y, Zhou K (2015) Polybrominated diphenyl ethers with potent and broad spectrum antimicrobial activity from the marine sponge Dysidea. Bioorg Med Chem Lett 25:2181–2183CrossRefPubMed Sun S, Canning CB, Bhargava K, Sun X, Zhu W, Zhou N, Zhang Y, Zhou K (2015) Polybrominated diphenyl ethers with potent and broad spectrum antimicrobial activity from the marine sponge Dysidea. Bioorg Med Chem Lett 25:2181–2183CrossRefPubMed
17.
Zurück zum Zitat Sionov E, Roth D, Sandovsky-Losica H, Kashman Y, Rudi A, Chill L, Berdicevsky I, Segal E (2005) Antifungal effect and possible mode of activity of a compound from the marine sponge Dysidea herbacea. J Infect 50:453–460CrossRefPubMed Sionov E, Roth D, Sandovsky-Losica H, Kashman Y, Rudi A, Chill L, Berdicevsky I, Segal E (2005) Antifungal effect and possible mode of activity of a compound from the marine sponge Dysidea herbacea. J Infect 50:453–460CrossRefPubMed
18.
Zurück zum Zitat Salam KA, Furuta A, Noda N, Tsuneda S, Sekiguchi Y, Yamashita A, Moriishi K, Nakakoshi M, Tani H, Roy SR, Tanaka J, Tsubuki M, Akimitsu N (2014) PBDE: structure-activity studies for the inhibition of hepatitis C virus NS3 helicase. Molecules 19:4006–4020CrossRefPubMed Salam KA, Furuta A, Noda N, Tsuneda S, Sekiguchi Y, Yamashita A, Moriishi K, Nakakoshi M, Tani H, Roy SR, Tanaka J, Tsubuki M, Akimitsu N (2014) PBDE: structure-activity studies for the inhibition of hepatitis C virus NS3 helicase. Molecules 19:4006–4020CrossRefPubMed
19.
Zurück zum Zitat Yamashita A, Fujimoto Y, Tamaki M, Setiawan A, Tanaka T, Okuyama-Dobashi K, Kasai H, Watashi K, Wakita T, Toyama M, Baba M, de Voogd NJ, Maekawa S, Enomoto N, Tanaka J, Moriishi K (2015) Identification of antiviral agents targeting hepatitis B virus promoter from extracts of Indonesian marine organisms by a novel cell-based screening assay. Mar Drugs 13:6759–6773CrossRefPubMedPubMedCentral Yamashita A, Fujimoto Y, Tamaki M, Setiawan A, Tanaka T, Okuyama-Dobashi K, Kasai H, Watashi K, Wakita T, Toyama M, Baba M, de Voogd NJ, Maekawa S, Enomoto N, Tanaka J, Moriishi K (2015) Identification of antiviral agents targeting hepatitis B virus promoter from extracts of Indonesian marine organisms by a novel cell-based screening assay. Mar Drugs 13:6759–6773CrossRefPubMedPubMedCentral
20.
Zurück zum Zitat Liu H, Namikoshi M, Meguro S, Nagai H, Kobayashi H, Yao X (2004) Isolation and characterization of polybrominated diphenyl ethers as inhibitors of microtubule assembly from the marine sponge Phyllospongia dendyi collected at Palau. J Nat Prod 67:472–474CrossRefPubMed Liu H, Namikoshi M, Meguro S, Nagai H, Kobayashi H, Yao X (2004) Isolation and characterization of polybrominated diphenyl ethers as inhibitors of microtubule assembly from the marine sponge Phyllospongia dendyi collected at Palau. J Nat Prod 67:472–474CrossRefPubMed
21.
Zurück zum Zitat Xu Y, Johnson RK, Hecht SM (2005) Polybrominated diphenyl ethers from a sponge of the Dysidea genus that inhibit Tie2 kinase. Bioorg Med Chem 13:657–659CrossRefPubMed Xu Y, Johnson RK, Hecht SM (2005) Polybrominated diphenyl ethers from a sponge of the Dysidea genus that inhibit Tie2 kinase. Bioorg Med Chem 13:657–659CrossRefPubMed
23.
Zurück zum Zitat Lee AS (2007) GRP78 Induction in cancer: therapeutic and prognostic implications. Cancer Res 67:3496–3499CrossRefPubMed Lee AS (2007) GRP78 Induction in cancer: therapeutic and prognostic implications. Cancer Res 67:3496–3499CrossRefPubMed
Metadaten
Titel
Marine spongean polybrominated diphenyl ethers, selective growth inhibitors against the cancer cells adapted to glucose starvation, inhibits mitochondrial complex II
Publikationsdatum
23.07.2016
Erschienen in
Journal of Natural Medicines / Ausgabe 1/2017
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-016-1025-x

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