BE-40644

BE-40644

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Category Enzyme inhibitors
Catalog number BBF-03239
CAS 172923-88-5
Molecular Weight 358.47
Molecular Formula C22H30O4

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Description

BE-40644 is an inhibitor of human Thioredoxin system produced by Actinoplanes sp. A40644. It can inhibit the growth of several tumor cells.

Specification

Synonyms 4,4,6aalpha,12bbeta-Tetramethyl-9-(hydroxymethyl)-1,3,4,4aalpha,5,6,6a,12,12aalpha,12b-decahydro-2H-benzo[a]xanthene-8,11-dione
IUPAC Name (4aR,6aR,12aS,12bR)-9-(hydroxymethyl)-4,4,6a,12b-tetramethyl-1,2,3,4a,5,6,12,12a-octahydrobenzo[a]xanthene-8,11-dione
Canonical SMILES CC1(CCCC2(C1CCC3(C2CC4=C(O3)C(=O)C(=CC4=O)CO)C)C)C
InChI InChI=1S/C22H30O4/c1-20(2)7-5-8-21(3)16(20)6-9-22(4)17(21)11-14-15(24)10-13(12-23)18(25)19(14)26-22/h10,16-17,23H,5-9,11-12H2,1-4H3/t16-,17+,21-,22-/m1/s1
InChI Key JJCFWPNMYFMHEH-WOSNLTMFSA-N

Properties

Appearance Yellow Powder
Antibiotic Activity Spectrum neoplastics (Tumor)
Boiling Point 480.7±34.0°C at 760 mmHg
Density 1.2±0.1 g/cm3
Solubility Soluble in Methanol, Chloroform, water

Reference Reading

1. Studies on biosynthetic genes and enzymes of isoprenoids produced by actinomycetes
Tohru Dairi J Antibiot (Tokyo). 2005 Apr;58(4):227-43. doi: 10.1038/ja.2005.27.
Most Streptomyces strains are equipped with only the 2-C-methyl-D-erythritol 4-phosphate (MEP) pathway for the formation of isopentenyl diphosphate, a common precursor of isoprenoids. In addition to this pathway, some Streptomyces strains possess the mevalonate (MV) pathway via which isoprenoid antibiotics are produced. We have recently cloned and analyzed the MV pathway gene clusters and their flanking regions from terpentecin, BE-40644, and furaquinocin A producers. All these clusters contained genes coding for mevalonate kinase, mevalonate diphosphate decarboxylase, phosphomevalonate kinase, type 2 IPP isomerase, HMG-CoA reductase, and HMG-CoA synthase. The order of each of the open reading frames (ORFs) is also the same, and the respective homologous ORFs show more than 70% amino acid identity with each other. In contrast to these conservative gene organizations, the biosynthetic genes of terpentecin, BE-40644, and furaquinocin A were located just upstream and/or downstream of the MV pathway gene cluster. These facts suggested that all the actinomycete strains possessing both the MV and MEP pathways produce isoprenoid compounds and the biosynthetic genes of one of these isoprenoids usually exist adjacent to the MV pathway gene cluster. Therefore, when the presence of the MV cluster is detected by molecular genetic techniques, isoprenoids may be produced by the cultivation of these actinomycete strains. During the course of these studies, we identified diterpene cyclases possessing unique primary structures that differ from those of eukaryotes and catalyze unique reactions.
2. First syntheses of (-)-tauranin and antibiotic (-)-BE-40644 based on lipase-catalyzed optical resolution of albicanol
Sadayuki Ishii, Mikio Fujii, Hiroyuki Akita Chem Pharm Bull (Tokyo). 2009 Oct;57(10):1103-6. doi: 10.1248/cpb.57.1103.
First syntheses of sesquiterpene quinones (-)-tauranin and (-)-BE-40644 which exhibited strong cytotoxicity against several cancer cell lines, were achieved from (8aS)-albicanol obtained by enzymatic optical resolution. By comparison of the sign of specific rotation between synthetic (12bS)-BE-40644 and natural (-)-BE-40644, the absolute configurations of natural (-)-BE-40644 were determined to be 4aS, 6aS, 12aR, 12bS.
3. A comparative analysis of the sugar phosphate cyclase superfamily involved in primary and secondary metabolism
Xiumei Wu, Patricia M Flatt, Oliver Schlörke, Axel Zeeck, Tohru Dairi, Taifo Mahmud Chembiochem. 2007 Jan 22;8(2):239-48. doi: 10.1002/cbic.200600446.
Sugar phosphate cyclases (SPCs) catalyze the cyclization of sugar phosphates to produce a variety of cyclitol intermediates that serve as the building blocks of many primary metabolites, for example, aromatic amino acids, and clinically relevant secondary metabolites, for example, aminocyclitol/aminoglycoside and ansamycin antibiotics. Feeding experiments with isotopically labeled cyclitols revealed that cetoniacytone A, a unique C(7)N-aminocyclitol antibiotic isolated from an insect endophytic Actinomyces sp., is derived from 2-epi-5-epi-valiolone, a product of SPC. By using heterologous probes from the 2-epi-5-epi-valiolone synthase class of SPCs, an SPC homologue gene, cetA, was isolated from the cetoniacytone producer. cetA is closely related to BE-orf9 found in the BE-40644 biosynthetic gene cluster from Actinoplanes sp. strain A40644. Recombinant expression of cetA and BE-orf9 and biochemical characterization of the gene products confirmed their function as 2-epi-5-epi-valiolone synthases. Further phylogenetic analysis of SPC sequences revealed a new clade of SPCs that might regulate the biosynthesis of a novel set of secondary metabolites.

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