Isoapoptolidin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04604 |
| CAS | 476647-30-0 |
| Molecular Weight | 1129.38 |
| Molecular Formula | C58H96O21 |
| Purity | >90% by HPLC |
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Description
It is a ring expanded isomer of apoptolidin originally isolated from Nocardiopsis sp. It demonstrates 10-fold reduced F1FO-ATP synthase inhibitory activity compared to apoptolidin (IC50s = 17 and 0.7 µM, respectively).
Specification
| Synonyms | (3E,5E,7E,9R,10R,11E,13E,17S,18S,20S,21R)-10-[(6-Deoxy-4-O-methyl-α-L-glucopyranosyl)oxy]-21-[O-2,6-dideoxy-3-O-methyl-β-D-arabino-hexopyranosyl-(1→4)-O-2,6-dideoxy-3-C-methyl-α-L-arabino-hexopyranosyl-(1→7)-2,4,6-trideoxy-1-C-hydroxy-2,4-dimethyl-8-O-methyl-L-glycero-β-D-galacto-octopyranosyl]-17,20-dihydroxy-18-methoxy-3,5,7,9,13-pentamethyloxacycloheneicosa-3,5,7,11,13-pentaen-2-one; Isoapoptolidin A |
| Storage | Store at -20°C |
| IUPAC Name | (3E,5E,7E,9R,10R,11E,13E,17S,18S,20S,21R)-21-[(2R,3R,4S,5R,6R)-2,4-dihydroxy-6-[(2R)-2-[(2R,4S,5S,6S)-4-hydroxy-5-[(2S,4R,5R,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4,6-dimethyloxan-2-yl]oxy-3-methoxypropyl]-3,5-dimethyloxan-2-yl]-10-[(2R,3S,4S,5R,6S)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy-17,20-dihydroxy-18-methoxy-3,5,7,9,13-pentamethyl-1-oxacyclohenicosa-3,5,7,11,13-pentaen-2-one |
| Canonical SMILES | CC1C=C(C=C(C=C(C(=O)OC(C(CC(C(CCC=C(C=CC1OC2C(C(C(C(O2)C)OC)O)O)C)O)OC)O)C3(C(C(C(C(O3)CC(COC)OC4CC(C(C(O4)C)OC5CC(C(C(O5)C)O)OC)(C)O)C)O)C)O)C)C)C |
| InChI | InChI=1S/C58H96O21/c1-29-17-16-18-40(59)44(69-13)25-41(60)54(78-55(65)33(5)23-31(3)21-30(2)22-32(4)42(20-19-29)76-56-51(64)50(63)52(71-15)37(9)74-56)58(67)35(7)48(61)34(6)43(79-58)24-39(28-68-12)75-47-27-57(11,66)53(38(10)73-47)77-46-26-45(70-14)49(62)36(8)72-46/h17,19-23,32,34-54,56,59-64,66-67H,16,18,24-28H2,1-15H3/b20-19+,29-17+,30-22+,31-21+,33-23+/t32-,34+,35-,36-,37+,38+,39-,40+,41+,42-,43-,44+,45-,46+,47+,48+,49-,50+,51+,52+,53+,54-,56+,57+,58-/m1/s1 |
| InChI Key | BGIXVQPJBLGABA-PVLPSINKSA-N |
| Source | Amycolatopsis sp. |
Properties
| Appearance | White Solid |
| Boiling Point | 1109.3±65.0°C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1.Isoapoptolidin: structure and activity of the ring-expanded isomer of apoptolidin.
Wender PA1, Gulledge AV, Jankowski OD, Seto H. Org Lett. 2002 Oct 31;4(22):3819-22.
[formula: see text] Apoptolidin (1) is a novel oncolytic lead that induces apoptosis in transformed cell lines with exceptional selectivity. We report the isolation and characterization of a ring-expanded macrolide isomer of apoptolidin: isoapoptolidin (2). The solution conformation of isoapoptolidin is described. The rate of isomerization was measured under biologically relevant conditions and found to approach equilibrium within the time frame of most cell-based assays. Isoapoptolidin's ability to inhibit mitochondrial F0F1-ATPase is over 10-fold less than that of apoptolidin.
2.Toward a stable apoptolidin derivative: identification of isoapoptolidin and selective deglycosylation of apoptolidin.
Pennington JD1, Williams HJ, Salomon AR, Sulikowski GA. Org Lett. 2002 Oct 31;4(22):3823-5.
[formula: see text] Isoapoptolidin was isolated from crude fermentation extracts of the apoptolidin-producing microorganism Nocardiopsis sp. Apoptolidin isomerizes to isoapoptolidin upon treatment with methanolic triethylamine to establish a 1.4:1 equilibrium mixture of isoapoptolidin and apoptolidin. Semisynthesis of a peracetylated and deglycosylated derivative of apoptolidin is also described.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
