Pluraflavin A
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| Category | Antibiotics |
| Catalog number | BBF-02035 |
| CAS | |
| Molecular Weight | 822.89 |
| Molecular Formula | C43H54N2O14 |
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Description
Pluraflavin A is an antitumor antibiotic produced by Saccharothrix sp. DSM 12931. Pluraflavin A has the effect of inhibiting the transcription of glucose-6-phosphatase gene and has good anti-proliferation activity on tumor cells.
Specification
| IUPAC Name | 5-[(4-amino-5-hydroxy-4,6-dimethyloxan-2-yl)oxymethyl]-10-[(2R,4S,5S,6S)-5-[(2S,4S,5S,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-(dimethylamino)-6-methyloxan-2-yl]-2-(2,3-dimethyloxiran-2-yl)-11-hydroxynaphtho[2,3-h]chromene-4,7,12-trione |
| Canonical SMILES | CC1C(C(CC(O1)OC2C(OC(CC2N(C)C)C3=C(C4=C(C=C3)C(=O)C5=C(C4=O)C6=C(C(=C5)COC7CC(C(C(O7)C)O)(C)N)C(=O)C=C(O6)C8(C(O8)C)C)O)C)O)O |
| InChI | InChI=1S/C43H54N2O14/c1-17-35(48)27(47)14-30(55-17)58-39-18(2)54-28(12-25(39)45(7)8)22-9-10-23-33(37(22)50)38(51)34-24(36(23)49)11-21(16-53-31-15-42(5,44)41(52)19(3)56-31)32-26(46)13-29(57-40(32)34)43(6)20(4)59-43/h9-11,13,17-20,25,27-28,30-31,35,39,41,47-48,50,52H,12,14-16,44H2,1-8H3/t17-,18-,19?,20?,25-,27-,28+,30-,31?,35+,39+,41?,42?,43?/m0/s1 |
| InChI Key | OHQJVUUBNSMDMH-IXTMJGLFSA-N |
Properties
| Appearance | Dark Orange Solid |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Boiling Point | 960.2±65.0°C at 760 mmHg |
| Density | 1.5±0.1 g/cm3 |
Reference Reading
1. Synthesis of pluraflavin A "aglycone"
Benjamin J D Wright, John Hartung, Feng Peng, Ryan Van de Water, Haibo Liu, Quen-Hui Tan, Ting-Chao Chou, Samuel J Danishefsky J Am Chem Soc. 2008 Dec 10;130(49):16786-90. doi: 10.1021/ja805936v.
The "aglycone" of pluraflavin A (2) has been synthesized. The key features of this synthesis include a 1,3-dipolar cycloaddition between a nitrile oxide (cf. 14) and an olefin (22) to yield an isoxazoline followed by subsequent conversion into the gamma-pyrone of pluraflavin A. The epoxide moiety linked to the pyrone is installed prior to Diels-Alder installation of the D ring, which allows access to a number of potentially active cytotoxic intermediates en route to the final compound. The preliminary in vitro results of two such compounds are also included with the racemic title compound exhibiting cytotoxicity in the nanomolar range.
2. Pluraflavins, potent antitumor antibiotics from Saccharothrix sp. DSM 12931
L Vértesy, F P Barbone, E Cashmen, H Decker, K Ehrlich, B Jordan, M Knauf, D Schummer, M P Segeth, J Wink, G Seibert J Antibiot (Tokyo). 2001 Sep;54(9):718-29. doi: 10.7164/antibiotics.54.718.
The new pluramycin-type antibiotics pluraflavin A, C43H54N2O14, pluraflavin B, C43H56N2O15, and pluraflavin E, C36H41NO14 were isolated from cultures of the Saccharothrix species DSM 12931. The structures of the novel compounds were elucidated with the aid of 2D NMR and mass spectrometric investigations. The characteristic structural element of pluraflavins A and B is an additional 4-epi-vancosamine unit at position 13 of the anthraquinone-gamma-pyrone ring system. Pluraflavin E has a carboxyl group in this position. Pluraflavin A has a reactive dimethyl epoxide side chain at position 2 of the anthraquinone-gamma-pyrone aglycon, which may explain the high activity of the antibiotic. The outstanding biological characteristic of pluraflavin A is its powerful, organ-dependent cytostatic action: the IC50 in the colon carcinoma proliferation assay is in the subnanomolar range.
3. Studies toward the total synthesis of pluraflavin A
John Hartung, Benjamin J D Wright, Samuel J Danishefsky Chemistry. 2014 Jul 7;20(28):8731-6. doi: 10.1002/chem.201402254. Epub 2014 Jun 12.
A synthetic strategy towards the potent cytostatic agent pluraflavin A has been developed. Formation of the enantioenriched anthrapyran core bearing a halogen atom enabled the introduction of the α C-aryl glycoside by Stille cross-coupling and subsequent hydrogenation of the aryl glycal. Chemo- and stereoselective O-glycosylations of α oliose and β 3-epi vancosamine residues afforded a fully glycosylated aromatic core. Attempts to install the dimethylamino group of the C-disaccharide suggest that introduction of an azide group by displacement and subsequent reduction may pave the way to the total synthesis of pluraflavin A.
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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 ╳
