Bisucaberin | CAS#112972-60-8 | Anticancer siderophore

MedKoo Cat#: 464719 | Name: Bisucaberin

Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Bisucaberin is a siderophore and bacterial metabolite that has been found in A. haloplanktis and has anticancer activity. It inhibits the growth of L1210 and 1MC carcinoma cells (IC50s = 9.7 and 12.7 µM, respectively) and sensitizes fibrosarcoma 1023 cells to macrophage-mediated cytolysis.

Chemical Structure

Bisucaberin

CAS#112972-60-8

Theoretical Analysis

MedKoo Cat#: 464719

Name: Bisucaberin

CAS#: 112972-60-8

Chemical Formula: C18H32N4O6

Exact Mass: 400.2322

Molecular Weight: 400.48

Elemental Analysis: C, 53.99; H, 8.05; N, 13.99; O, 23.97

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 885.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Bisucaberin; NSC 619796; NSC619796; NSC-619796;

IUPAC/Chemical Name

1,12-dihydroxy-1,6,12,17-tetraazacyclodocosane-2,5,13,16-tetraone

InChi Key

GTADQMQBQBOJIO-UHFFFAOYSA-N

InChi Code

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)

SMILES Code

O=C1N(CCCCCNC(CCC(N(CCCCCNC(CC1)=O)O)=O)=O)O

Appearance

Solid powder

Purity

>90% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 400.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Rütschlin S, Böttcher T. Engineering siderophores. Methods Enzymol. 2020;633:29-47. doi: 10.1016/bs.mie.2019.10.030. Epub 2019 Nov 20. PMID: 32046852. 2: Fujita MJ, Goto Y, Sakai R. Cloning of the Bisucaberin B Biosynthetic Gene Cluster from the Marine Bacterium Tenacibaculum mesophilum, and Heterologous Production of Bisucaberin B. Mar Drugs. 2018 Sep 19;16(9):342. doi: 10.3390/md16090342. PMID: 30235820; PMCID: PMC6164419. 3: Codd R, Soe CZ, Pakchung AAH, Sresutharsan A, Brown CJM, Tieu W. The chemical biology and coordination chemistry of putrebactin, avaroferrin, bisucaberin, and alcaligin. J Biol Inorg Chem. 2018 Oct;23(7):969-982. doi: 10.1007/s00775-018-1585-1. Epub 2018 Jun 26. PMID: 29946977. 4: Rütschlin S, Gunesch S, Böttcher T. One Enzyme To Build Them All: Ring-Size Engineered Siderophores Inhibit the Swarming Motility of Vibrio. ACS Chem Biol. 2018 May 18;13(5):1153-1158. doi: 10.1021/acschembio.8b00084. Epub 2018 Apr 19. PMID: 29653054. 5: Thode SK, Rojek E, Kozlowski M, Ahmad R, Haugen P. Distribution of siderophore gene systems on a Vibrionaceae phylogeny: Database searches, phylogenetic analyses and evolutionary perspectives. PLoS One. 2018 Feb 14;13(2):e0191860. doi: 10.1371/journal.pone.0191860. PMID: 29444108; PMCID: PMC5812596. 6: Sresutharsan A, Tieu W, Richardson-Sanchez T, Soe CZ, Codd R. Dimeric and trimeric homo- and heteroleptic hydroxamic acid macrocycles formed using mixed- ligand Fe(III)-based metal-templated synthesis. J Inorg Biochem. 2017 Dec;177:344-351. doi: 10.1016/j.jinorgbio.2017.07.033. Epub 2017 Aug 1. PMID: 28797801. 7: Thode SK, Bækkedal C, Söderberg JJ, Hjerde E, Hansen H, Haugen P. Construction of a fur null mutant and RNA-sequencing provide deeper global understanding of the Aliivibrio salmonicida Fur regulon. PeerJ. 2017 Jul 13;5:e3461. doi: 10.7717/peerj.3461. PMID: 28717590; PMCID: PMC5511505. 8: Arp J, Stallforth P. Rationalizing the Right Ratios. Cell Chem Biol. 2017 May 18;24(5):539-541. doi: 10.1016/j.chembiol.2017.05.007. PMID: 28525766. 9: Soe CZ, Telfer TJ, Levina A, Lay PA, Codd R. Simultaneous biosynthesis of putrebactin, avaroferrin and bisucaberin by Shewanella putrefaciens and characterisation of complexes with iron(III), molybdenum(VI) or chromium(V). J Inorg Biochem. 2016 Sep;162:207-215. doi: 10.1016/j.jinorgbio.2015.12.008. Epub 2015 Dec 17. PMID: 26723537. 10: Thode SK, Kahlke T, Robertsen EM, Hansen H, Haugen P. The immediate global responses of Aliivibrio salmonicida to iron limitations. BMC Microbiol. 2015 Feb 4;15(1):9. doi: 10.1186/s12866-015-0342-7. PMID: 25649684; PMCID: PMC4324432. 11: Fujita MJ, Sakai R. Production of avaroferrin and putrebactin by heterologous expression of a deep-sea metagenomic DNA. Mar Drugs. 2014 Sep 12;12(9):4799-809. doi: 10.3390/md12094799. PMID: 25222668; PMCID: PMC4178481. 12: Böttcher T, Clardy J. A chimeric siderophore halts swarming Vibrio. Angew Chem Int Ed Engl. 2014 Mar 24;53(13):3510-3. doi: 10.1002/anie.201310729. Epub 2014 Feb 24. Erratum in: Angew Chem Int Ed Engl. 2014 May 12;53(20):4994. PMID: 24615751; PMCID: PMC4040223. 13: Soe CZ, Codd R. Unsaturated macrocyclic dihydroxamic acid siderophores produced by Shewanella putrefaciens using precursor-directed biosynthesis. ACS Chem Biol. 2014 Apr 18;9(4):945-56. doi: 10.1021/cb400901j. Epub 2014 Feb 5. PMID: 24483365. 14: Fujita MJ, Nakano K, Sakai R. Bisucaberin B, a linear hydroxamate class siderophore from the marine bacterium Tenacibaculum mesophilum. Molecules. 2013 Apr 2;18(4):3917-26. doi: 10.3390/molecules18043917. PMID: 23549298; PMCID: PMC6270104. 15: Fujita MJ, Kimura N, Yokose H, Otsuka M. Heterologous production of bisucaberin using a biosynthetic gene cluster cloned from a deep sea metagenome. Mol Biosyst. 2012 Feb;8(2):482-5. doi: 10.1039/c1mb05431g. Epub 2011 Nov 3. PMID: 22051782. 16: Kadi N, Song L, Challis GL. Bisucaberin biosynthesis: an adenylating domain of the BibC multi-enzyme catalyzes cyclodimerization of N-hydroxy-N- succinylcadaverine. Chem Commun (Camb). 2008 Nov 7;(41):5119-21. doi: 10.1039/b813029a. Epub 2008 Sep 22. PMID: 18956041. 17: Winkelmann G, Schmid DG, Nicholson G, Jung G, Colquhoun DJ. Bisucaberin--a dihydroxamate siderophore isolated from Vibrio salmonicida, an important pathogen of farmed Atlantic salmon (Salmo salar). Biometals. 2002 Jun;15(2):153-60. doi: 10.1023/a:1015206419613. PMID: 12046923. 18: Hou Z, Raymond KN, O'Sullivan B, Esker TW, Nishio T. A Preorganized Siderophore: Thermodynamic and Structural Characterization of Alcaligin and Bisucaberin, Microbial Macrocyclic Dihydroxamate Chelating Agents(1). Inorg Chem. 1998 Dec 28;37(26):6630-6637. doi: 10.1021/ic9810182. PMID: 11670794. 19: Takahashi A, Nakamura H, Kameyama T, Kurasawa S, Naganawa H, Okami Y, Takeuchi T, Umezawa H, Iitaka Y. Bisucaberin, a new siderophore, sensitizing tumor cells to macrophage-mediated cytolysis. II. Physico-chemical properties and structure determination. J Antibiot (Tokyo). 1987 Dec;40(12):1671-6. doi: 10.7164/antibiotics.40.1671. PMID: 2962973. 20: Kameyama T, Takahashi A, Kurasawa S, Ishizuka M, Okami Y, Takeuchi T, Umezawa H. Bisucaberin, a new siderophore, sensitizing tumor cells to macrophage-mediated cytolysis. I. Taxonomy of the producing organism, isolation and biological properties. J Antibiot (Tokyo). 1987 Dec;40(12):1664-70. doi: 10.7164/antibiotics.40.1664. PMID: 2962972.