Synonym
Grisorixin; Desoxynigericin
IUPAC/Chemical Name
2-((3S,6R)-6-(((5R,7R,9R,10R)-2-((3'S,5'R)-5'-((2S,3S,5R,6S)-6-hydroxy-3,5,6-trimethyltetrahydro-2H-pyran-2-yl)-2,3'-dimethyloctahydro-[2,2'-bifuran]-5-yl)-9-methoxy-2,4,10-trimethyl-1,6-dioxaspiro[4.5]decan-7-yl)methyl)-3-methyltetrahydro-2H-pyran-2-yl)propanoic acid
InChi Key
ZITSQIZMRMDQLE-RHQSYKMPSA-N
InChi Code
InChI=1S/C40H68O10/c1-21-12-13-28(45-33(21)26(6)36(41)42)18-29-19-30(44-11)27(7)40(47-29)25(5)20-38(9,50-40)32-14-15-37(8,48-32)35-23(3)17-31(46-35)34-22(2)16-24(4)39(10,43)49-34/h21-35,43H,12-20H2,1-11H3,(H,41,42)/t21-,22-,23-,24+,25?,26?,27+,28+,29+,30+,31+,32?,33?,34-,35?,37?,38?,39-,40+/m0/s1
SMILES Code
CO[C@@H]1C[C@H](O[C@@]2([C@@H]1C)OC(CC2C)(C3CCC(O3)(C4O[C@@H]([C@H]5O[C@](O)([C@@H](C[C@@H]5C)C)C)C[C@@H]4C)C)C)C[C@H]6CC[C@@H](C(C(C(O)=O)C)O6)C
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
708.97
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: Leulmi N, Sighel D, Defant A, Khenaka K, Boulahrouf A, Mancini I. Nigericin and grisorixin methyl ester from the Algerian soil-living Streptomyces youssoufiensis SF10 strain: a computational study on their epimeric structures and evaluation of glioblastoma stem cells growth inhibition. Nat Prod Res. 2019 Jan;33(2):266-273. doi: 10.1080/14786419.2018.1446014. Epub 2018 Mar 7. PMID: 29513090.
2: Gachon P, Kergomard A, Staron T, Esteve C. Grisorixin, an ionophorous antibiotic of the nigericin group. I. Fermentation, isolation, biological properties and structure. J Antibiot (Tokyo). 1975 May;28(5):345-50. doi: 10.7164/antibiotics.28.345. PMID: 809402.
3: Gachon P, Kergomard A. Grisorixin, an ionophorous antibiotic of the nigericin group. II. Chemical and structural study of grisorixin and some derivatives. J Antibiot (Tokyo). 1975 May;28(5):351-7. doi: 10.7164/antibiotics.28.351. PMID: 1165221.
4: Chollet-Debord F, Moins N, Renoux M, Gachon P. Effects of the ionophore grisorixin on myocardial function and metabolism in isolated perfused working rat heart under normoxic and hypoxic conditions. Can J Physiol Pharmacol. 1986 May;64(5):631-40. doi: 10.1139/y86-105. PMID: 3730948.
5: Oikawa H, Aihara Y, Ichihara A, Sakamura S. Accumulation of grisorixin caused by treating a nigericin-producing strain with a P-450 inhibitor. Biosci Biotechnol Biochem. 1992 Apr;56(4):684. doi: 10.1271/bbb.56.684. PMID: 1368213.
6: Mouslim J, Cuer A, David L, Tabet JC. Biosynthetic study on the polyether carboxylic antibiotic, nigericin production and biohydroxylation of grisorixin by nigericin-producing Streptomyces hygroscopicus NRRL B-1865. J Antibiot (Tokyo). 1995 Sep;48(9):1011-4. doi: 10.7164/antibiotics.48.1011. PMID: 7592045.
7: Maublant JC, Moins N, Gachon P, Ross MR, Davidson WD, Mena I. Effects of grisorixin on the distribution of thallium-201 and on the oxidative metabolism in cultured myocardial cells. J Nucl Med. 1985 Jun;26(6):626-9. PMID: 3998852.
8: Moins N, Gachon P, Maublant J. Myocardial imaging in dogs treated with grisorixin: relationship between thallium-201 uptake and coronary blood flow. J Nucl Med. 1982 Apr;23(4):330-6. PMID: 7069497.
9: Amblard G, Sandeaux R, Sandeaux J, Gavach C. Transport of potassium ions across planar lipid membranes by the antibiotic, grisorixin: I. The equilibrium state and self-diffusion K+ fluxes. J Membr Biol. 1985;88(1):15-23. doi: 10.1007/BF01871209. PMID: 4093953.
10: Sandeaux R, Seta P, Jeminet G, Alleaume M, Gavach C. The influence of pH on the conductance of lipid bimolecular membranes in relation to the alkaline ion transport induced by carboxylic carriers grisorixin, alborixin and monensin. Biochim Biophys Acta. 1978 Aug 17;511(3):499-508. doi: 10.1016/0005-2736(78)90284-5. PMID: 28761.
