IUPAC/Chemical Name
N,N'-((3,6-Dioxo-2,5-piperazinediyl)bis(trimethylene))bis(5-hydroxy-3-methyl-2-pentenamide)
InChi Key
CNQCBOHTKBVCFM-WXUKJITCSA-N
InChi Code
InChI=1S/C22H36N4O6/c1-15(7-11-27)13-19(29)23-9-3-5-17-21(31)26-18(22(32)25-17)6-4-10-24-20(30)14-16(2)8-12-28/h13-14,17-18,27-28H,3-12H2,1-2H3,(H,23,29)(H,24,30)(H,25,32)(H,26,31)/b15-13+,16-14+
SMILES Code
O=C(NC1CCCNC(/C=C(C)/CCO)=O)C(CCCNC(/C=C(C)/CCO)=O)NC1=O
Purity
>98% (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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
452.55
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: Hördt W, Römheld V, Winkelmann G. Fusarinines and dimerum acid, mono- and dihydroxamate siderophores from Penicillium chrysogenum, improve iron utilization by strategy I and strategy II plants. Biometals. 2000 Mar;13(1):37-46. doi: 10.1023/a:1009234612486. PMID: 10831223.
2: Diekmann H. Stoffwechselprodukte von Mikroorganismen. 81. Vorkommen und Strukturen von Coprogen B und Dimerumsäure [Metabolic products of microorganisms. 81. Occurrence and structures of coprogen B and dimerum acid]. Arch Mikrobiol. 1970;73(1):65-76. German. PMID: 5484314.
3: Jalal MA, Love SK, van der Helm D. Siderophore mediated iron(III) uptake in Gliocladium virens. 1. Properties of cis-fusarinine, trans-fusarinine, dimerum acid, and their ferric complexes. J Inorg Biochem. 1986 Dec;28(4):417-30. doi: 10.1016/0162-0134(86)80027-7. PMID: 2950205.
4: Taira J, Miyagi C, Aniya Y. Dimerumic acid as an antioxidant from the mold, Monascus anka: the inhibition mechanisms against lipid peroxidation and hemeprotein-mediated oxidation. Biochem Pharmacol. 2002 Mar 1;63(5):1019-26. doi: 10.1016/s0006-2952(01)00923-6. PMID: 11911855.
5: Tseng WT, Hsu YW, Pan TM. Neuroprotective effects of dimerumic acid and deferricoprogen from Monascus purpureus NTU 568-fermented rice against 6-hydroxydopamine-induced oxidative stress and apoptosis in differentiated pheochromocytoma PC-12 cells. Pharm Biol. 2016 Aug;54(8):1434-44. doi: 10.3109/13880209.2015.1104698. Epub 2016 Jan 21. PMID: 26794209.
6: Howard DH, Rafie R, Tiwari A, Faull KF. Hydroxamate siderophores of Histoplasma capsulatum. Infect Immun. 2000 Apr;68(4):2338-43. doi: 10.1128/iai.68.4.2338-2343.2000. PMID: 10722639; PMCID: PMC97423.
7: Yamashiro J, Shiraishi S, Fuwa T, Horie T. Dimerumic acid protected oxidative stress-induced cytotoxicity in isolated rat hepatocytes. Cell Biol Toxicol. 2008 Aug;24(4):283-90. doi: 10.1007/s10565-007-9037-7. Epub 2007 Nov 9. PMID: 17992573.
8: Yano K, Sekine S, Nemoto K, Fuwa T, Horie T. The effect of dimerumic acid on LPS-induced downregulation of Mrp2 in the rat. Biochem Pharmacol. 2010 Aug 15;80(4):533-9. doi: 10.1016/j.bcp.2010.04.036. Epub 2010 May 8. PMID: 20457138.
9: Arias AA, Lambert S, Martinet L, Adam D, Tenconi E, Hayette MP, Ongena M, Rigali S. Growth of desferrioxamine-deficient Streptomyces mutants through xenosiderophore piracy of airborne fungal contaminations. FEMS Microbiol Ecol. 2015 Jul;91(7):fiv080. doi: 10.1093/femsec/fiv080. Epub 2015 Jul 15. PMID: 26183915.
10: Lehner SM, Atanasova L, Neumann NK, Krska R, Lemmens M, Druzhinina IS, Schuhmacher R. Isotope-assisted screening for iron-containing metabolites reveals a high degree of diversity among known and unknown siderophores produced by Trichoderma spp. Appl Environ Microbiol. 2013 Jan;79(1):18-31. doi: 10.1128/AEM.02339-12. Epub 2012 Oct 12. PMID: 23064341; PMCID: PMC3536107.
11: Wilhite SE, Lumsden RD, Straney DC. Peptide synthetase gene in Trichoderma virens. Appl Environ Microbiol. 2001 Nov;67(11):5055-62. doi: 10.1128/AEM.67.11.5055-5062.2001. PMID: 11679326; PMCID: PMC93271.
12: Timmerman MM, Woods JP. Potential role for extracellular glutathione- dependent ferric reductase in utilization of environmental and host ferric compounds by Histoplasma capsulatum. Infect Immun. 2001 Dec;69(12):7671-8. doi: 10.1128/IAI.69.12.7671-7678.2001. PMID: 11705947; PMCID: PMC98861.
13: Huang ZH, Liang X, Qi SH. A new iron(III) chelator of coprogen-type siderophore from the deep-sea-derived fungus Mycosphaerella sp. SCSIO z059. Chin J Nat Med. 2020 Apr;18(4):243-249. doi: 10.1016/S1875-5364(20)30029-7. PMID: 32402399.
14: Jalal MA, Love SK, van der Helm D. Siderophore mediated iron(III) uptake in Gliocladium virens. 2. Role of ferric mono- and dihydroxamates as iron transport agents. J Inorg Biochem. 1987 Apr;29(4):259-67. doi: 10.1016/0162-0134(87)80033-8. PMID: 2953864.
