Trachycladindoles A-G:: cytotoxic heterocycles from an Australian marine sponge, Trachycladus laevispirulifer

被引:30
作者
Capon, Robert J. [1 ]
Peng, Chongsheng [2 ]
Dooms, Cedric [1 ]
机构
[1] Univ Queensland, Inst Mol Biosci, St Lucia, Qld 4072, Australia
[2] Shanghai Jiao Tong Univ, Sch Pharm, Shanghai 200249, Peoples R China
关键词
D O I
10.1039/b803455a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A southern Australian marine sponge, Trachycladus laevispirulifer, yielded the cytotoxic agents trachycladindoles A-G (1-7) as a selection of novel indole-2-carboxylic acids bearing a 2-amino-4,5-dihydroimidazole moiety. The trachycladindoles displayed promising selective cytotoxicity against a panel of human cancer cell lines and their structures were assigned on the basis of detailed spectroscopic analysis. Preliminary structure activity relationship (SAR) investigations by co-metabolite defined structural features key to the trachycladindole pharmacophore, highlighting an unusual bioactive molecular motif deserving of future investigation.
引用
收藏
页码:2765 / 2771
页数:7
相关论文
共 12 条
[1]   Screening enzyme-inhibitory activity in several ascidian species from Orkney Islands using protein tyrosine kinase (PTK) bioassay-guided fractionation [J].
Barenbrock, JS ;
Köck, M .
JOURNAL OF BIOTECHNOLOGY, 2005, 117 (03) :225-232
[2]   6-hydroxydiscodermindole, a new discodermindole from the marine sponge Discodermia polydiscus [J].
Cohen, J ;
Paul, GK ;
Gunasekera, SP ;
Longley, RE ;
Pomponi, SA .
PHARMACEUTICAL BIOLOGY, 2004, 42 (01) :59-61
[3]   3-[2-AMINO-2-IMIDAZOLIN-4-YL] ALANINE, 2-[2-AMINO-2-IMIDAZOLIN-4-YL] ACETIC-ACID, 2-AMINOIMIDAZOLE AND OTHER GUANIDINE DERIVATIVES IN TEPHROSIEAE [J].
FELLOWS, LE ;
POLHILL, RM ;
BELL, EA .
BIOCHEMICAL SYSTEMATICS AND ECOLOGY, 1978, 6 (03) :213-215
[4]   3-[2-AMINO-2-IMIDAZOLIN-4(5)-YL]ALANINE (ENDURACIDIDINE) AND 2-[2-AMINO-2-IMIDAZOLIN-4(5)-YL] ACETIC-ACID IN SEEDS OF LONCHOCARPUS-SERICEUS [J].
FELLOWS, LE ;
HIDER, RC ;
BELL, EA .
PHYTOCHEMISTRY, 1977, 16 (12) :1957-1959
[5]   Mannopeptimycins, novel antibacterial glycopeptides from Streptomyces hygroscopicus, LL-AC98 [J].
He, HY ;
Williamson, RT ;
Shen, B ;
Graziani, EI ;
Yang, HY ;
Sakya, SM ;
Petersen, PJ ;
Carter, GT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (33) :9729-9736
[6]   Isolation and synthesis of a novel β-carboline guanidine derivative tiruchanduramine from the Indian ascidian Synoicum macroglossum [J].
Ravinder, K ;
Reddy, AV ;
Krishnaiah, P ;
Ramesh, P ;
Ramakrishna, S ;
Laatsch, H ;
Venkateswarlu, Y .
TETRAHEDRON LETTERS, 2005, 46 (33) :5475-5478
[7]   TUBASTRINE, A NEW GUANIDINOSTYRENE FROM THE CORAL TUBASTREA-AUREA [J].
SAKAI, R ;
HIGA, T .
CHEMISTRY LETTERS, 1987, (01) :127-128
[8]   TRACHYCLADINE-A AND TRACHYCLADINE-B - 2'-C-METHYL-5'-DEOXYRIBOFURANOSYL NUCLEOSIDES FROM THE MARINE SPONGE TRACHYCLADUS LAEVISPIRULIFER [J].
SEARLE, PA ;
MOLINSKI, TF .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (13) :4296-4298
[9]   A BROMINATED (AMINOIMIDAZOLINYL)INDOLE FROM THE SPONGE DISCODERMIA-POLYDISCUS [J].
SUN, HH ;
SAKEMI, S .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4307-4308
[10]   Solid-phase synthesis of oxathiocoraline by a key intermolecular disulfide dimer [J].
Tulla-Puche, Judit ;
Bayo-Puxan, Nuria ;
Moreno, Juan A. ;
Francesch, Andres M. ;
Cuevas, Carmen ;
Alvarez, Mercedes ;
Albericio, Fernando .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (17) :5322-+