Synonym
Ilicicolin B; LL-Z 1272beta; LL Z 1272beta; LLZ 1272beta;
IUPAC/Chemical Name
2,4-dihydroxy-6-methyl-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)benzaldehyde
InChi Key
QAPOXOGEDXIOHD-VZRGJMDUSA-N
InChi Code
InChI=1S/C23H32O3/c1-16(2)8-6-9-17(3)10-7-11-18(4)12-13-20-22(25)14-19(5)21(15-24)23(20)26/h8,10,12,14-15,25-26H,6-7,9,11,13H2,1-5H3/b17-10+,18-12+
SMILES Code
O=CC1=C(C)C=C(O)C(C/C=C(C)/CC/C=C(C)/CC/C=C(C)\C)=C1O
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
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
356.50
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: Gutiérrez M, Theoduloz C, Rodríguez J, Lolas M, Schmeda-Hirschmann G. Bioactive metabolites from the fungus Nectria galligena, the main apple canker agent in Chile. J Agric Food Chem. 2005 Oct 5;53(20):7701-8. PubMed PMID: 16190620.
2: Ding MG, Butler CA, Saracco SA, Fox TD, Godard F, di Rago JP, Trumpower BL. Introduction of cytochrome b mutations in Saccharomyces cerevisiae by a method that allows selection for both functional and non-functional cytochrome b proteins. Biochim Biophys Acta. 2008 Sep;1777(9):1147-56. doi: 10.1016/j.bbabio.2008.04.029. Epub 2008 Apr 27. PubMed PMID: 18498758; PubMed Central PMCID: PMC2601669.
3: Covian R, Trumpower BL. Ilicicolin Inhibition and Binding at Center N of the Dimeric Cytochrome bc1 Complex Reveal Electron Transfer and Regulatory Interactions between Monomers. J Biol Chem. 2009 Mar 27;284(13):8614-20. doi: 10.1074/jbc.M808914200. Epub 2009 Jan 27. PubMed PMID: 19176478; PubMed Central PMCID: PMC2659220.
4: Gutierrez-Cirlos EB, Merbitz-Zahradnik T, Trumpower BL. Inhibition of the yeast cytochrome bc1 complex by ilicicolin H, a novel inhibitor that acts at the Qn site of the bc1 complex. J Biol Chem. 2004 Mar 5;279(10):8708-14. Epub 2003 Dec 10. PubMed PMID: 14670947.
5: Ding MG, di Rago JP, Trumpower BL. Investigating the Qn site of the cytochrome bc1 complex in Saccharomyces cerevisiae with mutants resistant to ilicicolin H, a novel Qn site inhibitor. J Biol Chem. 2006 Nov 24;281(47):36036-43. Epub 2006 Sep 20. PubMed PMID: 16987808.
6: Wu B, Oesker V, Wiese J, Malien S, Schmaljohann R, Imhoff JF. Spirocyclic drimanes from the marine fungus Stachybotrys sp. strain MF347. Mar Drugs. 2014 Apr 1;12(4):1924-38. doi: 10.3390/md12041924. PubMed PMID: 24694571; PubMed Central PMCID: PMC4012445.
7: Rotsaert FA, Ding MG, Trumpower BL. Differential efficacy of inhibition of mitochondrial and bacterial cytochrome bc1 complexes by center N inhibitors antimycin, ilicicolin H and funiculosin. Biochim Biophys Acta. 2008 Feb;1777(2):211-9. Epub 2007 Nov 1. PubMed PMID: 18022381; PubMed Central PMCID: PMC2677292.
