Bisucaberin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00578 |
| CAS | 112972-60-8 |
| Molecular Weight | 400.47 |
| Molecular Formula | C18H32N4O6 |
| Purity | 95% |
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Description
Bisucaberin is a siderophore anti-tumor antibiotic produced by the monosporium Alteromonas haloplanktis SB-1123 obtained from deep sea sludge. It can bind high iron ions and has a specific inhibitory effect on tumor cell DNA synthesis.
Specification
| Synonyms | 1,12-Dihydroxy-1,6,12,17tetraaza-cyclodocosane-2,5,13,16-tetraone |
| IUPAC Name | 1,12-dihydroxy-1,6,12,17-tetrazacyclodocosane-2,5,13,16-tetrone |
| Canonical SMILES | C1CCNC(=O)CCC(=O)N(CCCCCNC(=O)CCC(=O)N(CC1)O)O |
| InChI | InChI=1S/C18H32N4O6/c23-15-7-10-18(26)22(28)14-6-2-4-12-20-16(24)8-9-17(25)21(27)13-5-1-3-11-19-15/h27-28H,1-14H2,(H,19,23)(H,20,24) |
| InChI Key | GTADQMQBQBOJIO-UHFFFAOYSA-N |
Properties
| Appearance | Colorless Crystal |
| Melting Point | 180°C(dec.) |
| Density | 1.162 g/cm3 |
Reference Reading
1.Bisucaberin B, a linear hydroxamate class siderophore from the marine bacterium Tenacibaculum mesophilum.
Fujita MJ1, Nakano K, Sakai R. Molecules. 2013 Apr 2;18(4):3917-26. doi: 10.3390/molecules18043917.
A siderophore, named bisucaberin B, was isolated from Tenacibaculum mesophilum bacteria separated from a marine sponge collected in the Republic of Palau. Using spectroscopic and chemical methods, the structure of bisucaberin B (1) was clearly determined to be a linear dimeric hydroxamate class siderophore. Although compound 1 is an open form of the known macrocyclic dimer bisucaberin (2), and was previously described as a bacterial degradation product of desferrioxamine B (4), the present report is the first description of the de novo biosynthesis of 1. To the best of our knowledge, compound 1 is the first chemically characterized siderophore isolated from a bacterium belonging to the phylum Bacteroidetes.
2.The immediate global responses of Aliivibrio salmonicida to iron limitations.
Thode SK1, Kahlke T2,3, Robertsen EM4, Hansen H5, Haugen P6. BMC Microbiol. 2015 Feb 4;15:9. doi: 10.1186/s12866-015-0342-7.
BACKGROUND: Iron is an essential micronutrient for all living organisms, and virulence and sequestration of iron in pathogenic bacteria are believed to be correlated. As a defence mechanism, potential hosts therefore keep the level of free iron inside the body to a minimum. In general, iron metabolism is well studied for some bacteria (mostly human or animal pathogens). However, this area is still under-investigated for a number of important bacterial pathogens. Aliivibrio salmonicida is a fish pathogen, and previous studies of this bacterium have shown that production of siderophores is temperature regulated and dependent on low iron conditions. In this work we studied the immediate changes in transcription in response to a sudden decrease in iron levels in cultures of A. salmonicida. In addition, we compared our results to studies performed with Vibrio cholerae and Vibrio vulnificus using a pan-genomic approach.
3.A chimeric siderophore halts swarming Vibrio.
Böttcher T1, Clardy J. Angew Chem Int Ed Engl. 2014 Mar 24;53(13):3510-3. doi: 10.1002/anie.201310729. Epub 2014 Feb 24.
Some bacteria swarm under some circumstances; they move rapidly and collectively over a surface. In an effort to understand the molecular signals controlling swarming, we isolated two bacterial strains from the same red seaweed, Vibrio alginolyticus B522, a vigorous swarmer, and Shewanella algae B516, which inhibits V. alginolyticus swarming in its vicinity. Plate assays combined with NMR, MS, and X-ray diffraction analyses identified a small molecule, which was named avaroferrin, as a potent swarming inhibitor. Avaroferrin, a previously unreported cyclic dihydroxamate siderophore, is a chimera of two well-known siderophores: putrebactin and bisucaberin. The sequenced genome of S. algae revealed avaroferrin's biosynthetic gene cluster to be a mashup of putrebactin and bisucaberin biosynthetic genes. Avaroferrin blocks swarming through its ability to bind iron in a form that cannot be pirated by V. alginolyticus, thereby securing this essential resource for its producer.
4.Heterologous production of bisucaberin using a biosynthetic gene cluster cloned from a deep sea metagenome.
Fujita MJ1, Kimura N, Yokose H, Otsuka M. Mol Biosyst. 2012 Feb;8(2):482-5. doi: 10.1039/c1mb05431g. Epub 2011 Nov 3.
A siderophore biosynthetic gene cluster was cloned from a metagenomic library generated from deep sea sediment. The gene cluster was successfully expressed in Escherichia coli to produce bisucaberin, a siderophore originally reported from the marine bacterium Alteromonas haloplanktis. The cloned bisucaberin biosynthetic gene cluster was moderately similar to that of the known bisucaberin producer Vibrio salmonicida. However, the cloned gene cluster consists of four genes rather than three genes found in the V. salmonicida cluster. The low overall homology of the amino acid and nucleotide sequences with those of other species suggests that the cloned genes were derived from one of the unsequenced bacteria including uncultured species.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
