Arisugacin A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00084 |
| CAS | |
| Molecular Weight | 496.55 |
| Molecular Formula | C28H32O8 |
| Purity | >98% |
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Description
Arisugacin is an acetylcholinesterase (AChE) inhibitor produced by Penicillum sp. FO-4259.
Specification
| Synonyms | Arisugacin; (4aR,6aR,12aS,12bS)-9-(3,4-dimethoxyphenyl)-4a,12a-dihydroxy-4,4,6a,12b-tetramethyl-4a,6,6a,12,12a,12b-hexahydro-4H,11H-benzo[f]pyrano[4,3-b]chromene-1,11(5H)-dione |
| Storage | Store at -20°C |
| IUPAC Name | (1S,2S,7R,10R)-14-(3,4-dimethoxyphenyl)-1,7-dihydroxy-2,6,6,10-tetramethyl-11,15-dioxatetracyclo[8.8.0.02,7.012,17]octadeca-4,12(17),13-triene-3,16-dione |
| Canonical SMILES | CC1(C=CC(=O)C2(C1(CCC3(C2(CC4=C(O3)C=C(OC4=O)C5=CC(=C(C=C5)OC)OC)O)C)O)C)C |
| InChI | InChI=1S/C28H32O8/c1-24(2)10-9-22(29)26(4)27(24,31)12-11-25(3)28(26,32)15-17-20(36-25)14-19(35-23(17)30)16-7-8-18(33-5)21(13-16)34-6/h7-10,13-14,31-32H,11-12,15H2,1-6H3/t25-,26+,27-,28-/m1/s1 |
| InChI Key | MIHBCQWIBJDVPX-JUDWXZBOSA-N |
Properties
| Appearance | White Powder |
| Melting Point | >300°C |
| Solubility | Soluble in DMSO |
Reference Reading
1. A computational view on the significance of E-ring in binding of (+)-arisugacin A to acetylcholinesterase
Ziyad F Al-Rashid, Richard P Hsung Bioorg Med Chem Lett. 2015 Nov 1;25(21):4848-4853. doi: 10.1016/j.bmcl.2015.06.047. Epub 2015 Jun 27.
A computational docking study of a series of de novo structural analogs of the highly potent, non-nitrogen containing, acetylcholinesterase inhibitor (+)-arisugacin A is presented. In direct comparison to the recently reported X-ray single-crystal structure of (+)-territrem B bound hAChE, the modeling suggests that there is a unique conformational preference for the E-ring that is responsible for the superior inhibitory activity of (+)-arisugacin A against hAChE relative to (+)-territrem B, and that substitutions on the E-ring also play an important role in the protein-ligand interaction.
2. The first total synthesis of (+/-)-arisugacin A, a potent, orally bioavailable inhibitor of acetylcholinesterase
Toshiaki Sunazuka, Masaki Handa, Kenichiro Nagai, Tatsuya Shirahata, Yoshihiro Harigaya, Kazuhiko Otoguro, Isao Kuwajima, Satoshi Omura Org Lett. 2002 Feb 7;4(3):367-9. doi: 10.1021/ol017046x.
The first convergent total synthesis of (+/-)-arisugacin A was accomplished by stereoselective construction of the arisugacin skeleton via a Knoevenagel-type reaction of an alpha,beta-unsaturated aldehyde with a 4-hydroxy 2-pyrone and stereoselective dihydroxylation followed by deoxygenation.
3. (+)-Arisugacin A--computational evidence of a dual binding site covalent inhibitor of acetylcholinesterase
Ziyad F Al-Rashid, Richard P Hsung Bioorg Med Chem Lett. 2011 May 1;21(9):2687-91. doi: 10.1016/j.bmcl.2010.12.041. Epub 2010 Dec 16.
A computation docking study of the highly potent, non-nitrogen containing, acetylcholinesterase inhibitor (+)-arisugacin A is presented. The model suggests that (+)-arisugacin A is a dual binding site covalent inhibitor of AChE. These findings are examined in the context of Alzheimer's disease-modifying therapeutic design. (+)-Arisugacin A's revealed mode of action is unique, and may serve as a basis for the development of AD therapeutics capable of treating the symptomatic aspects of AD, while being neuroprotective with long term efficacy.
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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 ╳
