Yoropyrazone, a new naphthopyridazone alkaloid isolated from Streptomyces sp. IFM 11307 and evaluation of its TRAIL resistance-overcoming activity

Journal of Antibiotics

Volumn 65, Issue 5, 2012, Pages 245-248

  Abdelfattah, Mohamed S ^a   Toume, Kazufumi ^b   Ishibashi, Masami ^b  

^a Helwan University   (Egypt)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

naphthopyridazone; Streptomyces sp.; TRAIL

Indexed keywords

ANTINEOPLASTIC AGENT; LUTEOLIN; PYRIDAZINE DERIVATIVE; TUMOR NECROSIS FACTOR RELATED APOPTOSIS INDUCING LIGAND; UNCLASSIFIED DRUG; YOROPYRAZONE;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER RESISTANCE; CONTROLLED STUDY; CYTOTOXICITY; DRUG ISOLATION; DRUG SCREENING; DRUG STRUCTURE; HUMAN; HUMAN CELL; PRIORITY JOURNAL; SPECTROSCOPY; STOMACH ADENOCARCINOMA; STREPTOMYCES;

ADENOCARCINOMA; ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL LINE, TUMOR; DRUG RESISTANCE, NEOPLASM; HUMANS; NAPHTHALENES; PYRAZOLES; SPECTRUM ANALYSIS; STOMACH NEOPLASMS; STREPTOMYCES; TNF-RELATED APOPTOSIS-INDUCING LIGAND;

STREPTOMYCES SP.;

EID: 84861598926     PISSN: 00218820     EISSN: 18811469     Source Type: Journal    
DOI: 10.1038/ja.2012.11     Document Type: Article

References (18)

1. Abdelfattah, M. S., Toume, K. & Ishibashi, M. Isolation and structure elucidation of izuminosides A-C: A rare phenazine glycosides from Streptomyces sp. IFM 11260. J. Antibiot. 64, 271-275 (2011).
2. Abdelfattah, M. S., Toume, K. & Ishibashi, M. Izumiphenazines A-C: Isolation and structure elucidation of phenazine derivatives from Streptomyces sp. IFM 11204. J. Nat. Prod. 73, 1999-2002 (2010).
3. Aida, W., Ohtsuki, T., Li, X. & Ishibashi, M. Isolation of new carbamate- or pyridinecontaining natural products, fuzanins A, B, C, and D from Kitasatospora sp. IFM10917. Tetrahedron 65, 369-373 (2009).
4. Abdelfattah, M. S., Toume, K. & Ishibashi, M. New pyranonaphthoquinones and phenazine alkaloid isolated from Streptomyces sp. IFM 11307 with TRAIL resistance-overcoming activity. J. Antibiot. 64, 729-734 (2011).
5. Ishibashi, M. & Ohtsuki, T. Studies on search for bioactive natural products targeting TRAIL signaling leading to tumor cell apoptosis. Med. Res. Rev. 28, 688-714 (2008).
6. Ahmed,F. et al. Constituents of Amoora cucullata with TRAIL resistance overcoming activity. Org. Biomol. Chem. 8, 3696-3703 (2010).
7. Kometani, T., Takeuchi, Y. & Yoshii, E. Pyranonaphthoquinone antibiotics. 4. Total synthesis of (+)-griseusin A, an enantiomer of the naturally occurring griseusin A. J. Org. Chem. 48, 2311-2314 (1983).
8. McNab, H. An analysis of the 13C n.m.r. spectra of pyridazin-3-ones and some specifically deuteriated derivatives. J. Chem. Soc., Perkin Trans. 1, 1203-1207 (1983).
9. Bhandari,R.et al. Structure of NG-061, a novel potentiator of nerve growth factor (NGF) isolated from Penicillium minioluteum F-4627. J. Antibiot. 52, 231-234 (1999).
10. Stefañ ska, B. et al. Synthesis and biological evaluation of 2,7-dihydro-3H-dibenzo [de,h]cinnoline-3,7-dione derivatives, a novel group of anticancer agents active on a multidrug resistant cell line. Bioorg. Med. Chem. 11, 561-572 (2003).
11. Igarashi, M. et al. 4¢-Deacetyl-(-)-griseusins A and B, new naphthoquinone antibiotics from an actinomycete. J. Antibiot. 48, 1502-1505 (1995).
12. Peng, X.- P. et al. Aromatic compounds from the halotolerant fungal strain of Wallemia sebi PXP-89 in ha hypersaline medium. Arch. Pharm. Res. 34, 907-912 (2011).
13. Chlipala, G. E. et al. Nhatrangins A and B, aplysiatoxin-related metabolites from the marine syanobacterium Lyngbya majuscule from Vietnam. J. Nat. Prod. 73, 784-787 (2010).
14. Stefañ ska, B. et al. 2,7-Dihydro-3H-pyridazino[5,4,3-kl] -Acridin-3-one derivatives, novel type of cytotoxic agents active on multidrug-resistant cell lines. Synthesis and biological evaluation. Bioorg. Med. Chem. 13, 1969-1975 (2005).
15. Srivastava, R. K. TRAIL/Apo-2L: Mechanisms and clinical applications in cancer. Neoplasia 3, 535-546 (2001).
16. Lindhagen, E., Mygren, P. & Larsson, R. The fluorometric microculture cytotoxicity assay. Nat. Protoc. 3, 1364-1369 (2008).
17. Horinaka, M. et al. Luteolin induces apoptosis via death receptor 5 up regulation in human malignant tumor cells. Oncogene 24, 7180-7189 (2005).
18. Shankar, S. & Srivastava, R. K. Enhancement of therapeutic potential of TRAIL by cancer chemotherapy and irradiation: Mechanisms and clinical implication. Drug Resist. Updat. 7, 139-156 (2004).