IUPAC/Chemical Name
N-[(E)-3-(2-Amino-1H-imidazol-5-yl)prop-2-enyl]-4-bromo-1H-pyrrole-2-carboxamide
InChi Key
KHJREOQCERRAME-OWOJBTEDSA-N
InChi Code
InChI=1S/C11H12BrN5O/c12-7-4-9(15-5-7)10(18)14-3-1-2-8-6-16-11(13)17-8/h1-2,4-6,15H,3H2,(H,14,18)(H3,13,16,17)/b2-1+
SMILES Code
O=C(C1=CC(Br)=CN1)NC/C=C/C2=CN=C(N)N2
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
>2 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
310.16
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: Sun Y, Ai X, Hou J, Ye X, Liu R, Shen S, Li Z, Lu S. Integrated discovery of FOXO1-DNA stabilizers from marine natural products to restore chemosensitivity to anti-EGFR-based therapy for metastatic lung cancer. Mol Biosyst. 2017 Jan 31;13(2):330-337. doi: 10.1039/c6mb00678g. PubMed PMID: 27966721.
2: Cychon C, Lichte E, Köck M. The marine sponge Agelas citrina as a source of the new pyrrole-imidazole alkaloids citrinamines A-D and N-methylagelongine. Beilstein J Org Chem. 2015 Oct 29;11:2029-37. doi: 10.3762/bjoc.11.220. eCollection 2015. PubMed PMID: 26664624; PubMed Central PMCID: PMC4660978.
3: Rasapalli S, Kumbam V, Dhawane AN, Golen JA, Lovely CJ, Rheingold AL. Total syntheses of oroidin, hymenidin and clathrodin. Org Biomol Chem. 2013 Jul 7;11(25):4133-7. doi: 10.1039/c3ob40668g. PubMed PMID: 23695419.
4: Scala F, Fattorusso E, Menna M, Taglialatela-Scafati O, Tierney M, Kaiser M, Tasdemir D. Bromopyrrole alkaloids as lead compounds against protozoan parasites. Mar Drugs. 2010 Jul 14;8(7):2162-74. doi: 10.3390/md8072162. PubMed PMID: 20714430; PubMed Central PMCID: PMC2920549.
5: Medeiros MA, Lourenço A, Tavares MR, Curto MJ, Feio SS, Roseiro JC. (-)-Agelasidine A from Agelas clathrodes. Z Naturforsch C. 2006 Jul-Aug;61(7-8):472-6. PubMed PMID: 16989304.
6: Pettit GR, Ducki S, Herald DL, Doubek DL, Schmidt JM, Chapuis JC. Antineoplastic agents 470. Absolute configuration of the marine sponge bromopyrrole agelastatin A. Oncol Res. 2005;15(1):11-20. PubMed PMID: 15839302.
7: Bickmeyer U, Drechsler C, Köck M, Assmann M. Brominated pyrrole alkaloids from marine Agelas sponges reduce depolarization-induced cellular calcium elevation. Toxicon. 2004 Jul;44(1):45-51. PubMed PMID: 15225561.
8: Assmann M, Zea S, Köck M. Sventrin, a new bromopyrrole alkaloid from the Caribbean sponge Agelas sventres. J Nat Prod. 2001 Dec;64(12):1593-5. PubMed PMID: 11754625.
9: Kobayashi J, Ohizumi Y, Nakamura H, Hirata Y. A novel antagonist of serotonergic receptors, hymenidin, isolated from the Okinawan marine sponge Hymeniacidon sp. Experientia. 1986 Oct 15;42(10):1176-7. PubMed PMID: 3770140.
