Apoptolidin
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| Category | Mycotoxins |
| Catalog number | BBF-00557 |
| CAS | 194874-06-1 |
| Molecular Weight | 1129.37 |
| Molecular Formula | C58H96O21 |
| Purity | ≥95% |
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Description
Apoptolidin is an apoptosis inducer produced by Nocardiopsis sp. Apoptolidin can induce apoptosis of metastatic cells, but has no effect on normal cells.
Specification
| Synonyms | (1R)-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→8)-3,5,7-trideoxy-1-C-[(2S,4S,5S,8E,10E,12R,13R,14E,16E,18E)-12-[(6-deoxy-4-O-methyl-α-L-glucopyranosyl)oxy]-5-hydroxy-4-methoxy-9,13,15,17,19-pentamethyl-20-oxooxacycloeicosa-8,10,14,16,18-pentaen-2-yl]-3,5-dimethyl-9-O-methyl-L-glycero-α-D-galacto-2-nonulopyranose; Apoptolidin A; FU 40A |
| Storage | Store at -20°C |
| IUPAC Name | (3E,5E,7E,9R,10R,11E,13E,17S,18S,20S)-20-[(R)-[(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]-hydroxymethyl]-10-[(2R,3S,4S,5R,6S)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy-17-hydroxy-18-methoxy-3,5,7,9,13-pentamethyl-1-oxacycloicosa-3,5,7,11,13-pentaen-2-one |
| Canonical SMILES | CC1C=C(C=C(C=C(C(=O)OC(CC(C(CCC=C(C=CC1OC2C(C(C(C(O2)C)OC)O)O)C)O)OC)C(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)O)C)C)C |
| InChI | InChI=1S/C58H96O21/c1-29-17-16-18-40(59)43(69-13)25-45(76-55(65)33(5)23-31(3)21-30(2)22-32(4)41(20-19-29)77-56-51(63)50(62)52(71-15)37(9)74-56)53(64)58(67)35(7)48(60)34(6)42(79-58)24-39(28-68-12)75-47-27-57(11,66)54(38(10)73-47)78-46-26-44(70-14)49(61)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 | WILMROCKORZEMQ-AIUMZUNXSA-N |
| Source | Amycolatopsis sp. |
Properties
| Appearance | Colorless Powder |
| Boiling Point | 1108.9±65.0°C at 760 mmHg |
| Melting Point | 128-130°C |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1.Apoptolidins E and F, new glycosylated macrolactones isolated from Nocardiopsis sp.
Wender PA1, Longcore KE. Org Lett. 2009 Dec 3;11(23):5474-7. doi: 10.1021/ol902308v.
Two new glycosylated macrolactones, apoptolidins E (5) and F (6), were isolated from fermentation of the actinomycete Nocardiopsis sp. and their structures assigned. Lacking the C16 and C20 oxygens of apoptolidin A (1), these macrolides are also the first members of this family to display a 4-O-methyl-l-rhamnose at C9 rather than a 6-deoxy-4-O-methyl-l-glucose.
2.Biosynthesis of the Apoptolidins in Nocardiopsis sp. FU 40.
Du Y1, Derewacz DK, Deguire SM, Teske J, Ravel J, Sulikowski GA, Bachmann BO. Tetrahedron. 2011 Sep 2;67(35):6568-6575.
The apoptolidins are 20/21-membered macrolides produced by Nocardiopsis sp. FU40. Several members of this family are potent and remarkably selective inducers of apoptosis in cancer cell lines, likely via a distinct mitochondria associated target. To investigate the biosynthesis of this natural product, the complete genome of the apoptolidin producer Nocardiopsis sp. FU40 was sequenced and a 116 Kb region was identified containing a putative apoptolidin biosynthetic gene cluster. The apoptolidin gene cluster comprises a type I polyketide synthase, with 13 homologating modules, apparently initiated in an unprecedented fashion via transfer from a methoxymalonyl-acyl carrier protein loading module. Spanning approximately 39 open reading frames, the gene cluster was cloned into a series of overlapping cosmids and functionally validated by targeted gene disruption experiments in the producing organism. Disruption of putative PKS and P(450) genes delineated the roles of these genes in apoptolidin biosynthesis and chemical complementation studies demonstrated intact biosynthesis peripheral to the disrupted genes.
3.Catalytic asymmetric aldol equivalents in the enantioselective synthesis of the apoptolidin C aglycone.
Vargo TR1, Hale JS, Nelson SG. Angew Chem Int Ed Engl. 2010 Nov 8;49(46):8678-81. doi: 10.1002/anie.201004925.
4.Fluorescent probes of the apoptolidins and their utility in cellular localization studies.
DeGuire SM1, Earl DC, Du Y, Crews BA, Jacobs AT, Ustione A, Daniel C, Chong KM, Marnett LJ, Piston DW, Bachmann BO, Sulikowski GA. Angew Chem Int Ed Engl. 2015 Jan 12;54(3):961-4. doi: 10.1002/anie.201408906. Epub 2014 Nov 27.
Apoptolidin A has been described among the top 0.1% most-cell-selective cytotoxic agents to be evaluated in the NCI 60 cell line panel. The molecular structure of apoptolidin A consists of a 20-membered macrolide with mono- and disaccharide moieties. In contrast to apoptolidin A, the aglycone (apoptolidinone) shows no cytotoxicity (>10 μM) when evaluated against several tumor cell lines. Apoptolidin H, the C27 deglycosylated analogue of apoptolidin A, displayed sub-micromolar activity against H292 lung carcinoma cells. Selective esterification of apoptolidins A and H with 5-azidopentanoic acid afforded azido-functionalized derivatives of potency equal to that of the parent macrolide. They also underwent strain-promoted alkyne-azido cycloaddition reactions to provide access to fluorescent and biotin-functionalized probes. Microscopy studies demonstrate apoptolidins A and H localize in the mitochondria of H292 human lung carcinoma cells.
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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 ╳
