Synonym
BARETTIN; (-)-Barettin; 104311-70-8; CHEMBL255898; (-)-Barettine;
IUPAC/Chemical Name
2-[3-[(2S,5Z)-5-[(6-bromo-1H-indol-3-yl)methylidene]-3,6-dioxopiperazin-2-yl]propyl]guanidine
InChi Key
YYFNNPXWRXQUPR-JVXNRYDGSA-N
InChi Code
InChI=1S/C17H19BrN6O2/c18-10-3-4-11-9(8-22-13(11)7-10)6-14-16(26)23-12(15(25)24-14)2-1-5-21-17(19)20/h3-4,6-8,12,22H,1-2,5H2,(H,23,26)(H,24,25)(H4,19,20,21)/b14-6-/t12-/m0/s1
SMILES Code
N/C(N)=N\CCC[C@@H](C(N/C1=C\C2=CNC3=C2C=CC(Br)=C3)=O)NC1=O
Appearance
To be determined
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
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
419.28
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: Labriere C, Cervin G, Pavia H, Hansen JH, Svenson J. Structure-Activity
Relationship Probing of the Natural Marine Antifoulant Barettin. Mar Biotechnol
(NY). 2021 Dec;23(6):904-916. doi: 10.1007/s10126-021-10074-z. Epub 2021 Nov 2.
PMID: 34727298.
2: Lind KF, Østerud B, Hansen E, Jørgensen TØ, Andersen JH. The immunomodulatory
effects of barettin and involvement of the kinases CAMK1α and RIPK2.
Immunopharmacol Immunotoxicol. 2015;37(5):458-64. doi:
10.3109/08923973.2015.1082584. PMID: 26466644.
3: Lind KF, Hansen E, Østerud B, Eilertsen KE, Bayer A, Engqvist M, Leszczak K,
Jørgensen TØ, Andersen JH. Antioxidant and anti-inflammatory activities of
barettin. Mar Drugs. 2013 Jul 22;11(7):2655-66. doi: 10.3390/md11072655. PMID:
23880935; PMCID: PMC3736444.
4: Labrière C, Andersen JH, Albrigtsen M, Hansen JH, Svenson J. Heterocyclic
cellular lipid peroxidation inhibitors inspired by the marine antioxidant
barettin. Bioorg Chem. 2019 Mar;84:106-114. doi: 10.1016/j.bioorg.2018.11.024.
Epub 2018 Nov 22. PMID: 30500520.
5: Kelley EW, Norman SG, Scheerer JR. Synthesis of monoalkylidene
diketopiperazines and application to the synthesis of barettin. Org Biomol Chem.
2017 Oct 18;15(40):8634-8640. doi: 10.1039/c7ob02297b. PMID: 28980696; PMCID:
PMC5678964.
