arsenicin A
{{Short description|Chemical compound}}
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 457817118
| ImageFileL1 = Arsenicin A.png
| ImageSizeL1 = 121
| ImageNameL1 = Structural formula of arsenicin A
| ImageFileR1 = Arsenicin-A-3D-spacefill.png
| ImageSizeR1 = 121
| ImageNameR1 = Spacefill model of arsenicin A
| PIN = 2,4,6-Trioxa-1,3,5,7-tetraarsaadamantane
|Section1={{Chembox Identifiers
| CASNo = 925705-41-5
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 597Y8O946Y
| PubChem = 16095534
| ChemSpiderID = 21430729
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| SMILES = [As@@]1(O2)C[As@](O[As@]2C3)O[As@]3C1
| SMILES1 = C1[As]2C[As]3O[As]1C[As](O2)O3
| StdInChI = 1S/C3H6As4O3/c1-4-2-6-9-5(1)3-7(8-4)10-6/h1-3H2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MHYDZXIVBJPPAM-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
|Section2={{Chembox Properties
| C=3 | H=6 | As=4 | O=3
| MeltingPtC = 182 to 184
}}
}}
Arsenicin A is a naturally occurring arsenic heterocycle with the molecular formula C3H6As4O3. It was first isolated from the New Caledonian marine sponge Echinochalina bargibanti.{{cite journal | doi = 10.1002/chem.200600783 | title = On the First Polyarsenic Organic Compound from Nature: Arsenicin a from the New Caledonian Marine Sponge Echinochalina bargibanti | year = 2006 | last1 = Mancini | first1 = Ines | last2 = Guella | first2 = Graziano | last3 = Frostin | first3 = Maryvonne | last4 = Hnawia | first4 = Edouard | last5 = Laurent | first5 = Dominique | last6 = Debitus | first6 = Cecile | last7 = Pietra | first7 = Francesco | journal = Chemistry: A European Journal | volume = 12 | pages = 8989–94 | pmid = 17039560 | issue = 35}} The compound was characterized by computational and spectroscopic{{cite journal | doi = 10.1002/chem.200801272 | title = Computational NMR Spectroscopy of Organoarsenicals and the Natural Polyarsenic Compound Arsenicin A | year = 2008 | last1 = Tähtinen | first1 = Petri | last2 = Saielli | first2 = Giacomo | last3 = Guella | first3 = Graziano | last4 = Mancini | first4 = Ines | last5 = Bagno | first5 = Alessandro | journal = Chemistry: A European Journal | volume = 14 | pages = 10445–52 | pmid = 18846604 | issue = 33}}{{cite journal | doi = 10.1039/b816729j | title = Vibrational analysis as a powerful tool in structure elucidation of polyarsenicals: a DFT-based investigation of arsenicin A | year = 2009 | last1 = Guella | first1 = Graziano | last2 = Mancini | first2 = Ines | last3=Mariotto | first3=Gino | last4=Rossi | first4 = Barbara | last5=Viliani | first5=Gabriele | journal = Physical Chemistry Chemical Physics | volume = 11| pages=2420–2427 | pmid = 19325974 | issue = 14| bibcode = 2009PCCP...11.2420G }} techniques and found to possess a cage-like structure similar to adamantane in which the four methanetriyl carbon bridgeheads are replaced by arsenic atoms and three of the six methylene bridges are replaced by oxygen atoms. It is the first polyarsenic compound ever found in nature. Subsequently, the proposed structure was prepared in large quantities via total synthesis and the structure was confirmed by x-ray crystallography.{{cite journal |author1=Di Lu |author2=A. David Rae |author3=Geoff Salem |author4=Michelle L. Weir |author5=Anthony C. Willis |author6=S. Bruce Wild | journal = Organometallics | year = 2010 | volume = 29 | issue = 1 | pages = 32–33 | doi = 10.1021/om900998q | title = Arsenicin A, A Natural Polyarsenical: Synthesis and Crystal Structure| hdl = 1885/58485 |s2cid=96366756 | hdl-access = free }}{{Cite journal|last1=Lu|first1=Di|last2=Coote|first2=Michelle L.|last3=Ho|first3=Junming|last4=Kilah|first4=Nathan L.|last5=Lin|first5=Ching-Yeh|last6=Salem|first6=Geoff|last7=Weir|first7=Michelle L.|last8=Willis|first8=Anthony C.|last9=Wild|first9=S. Bruce|date=2012-03-12|title=Resolution and Improved Synthesis of (±)-Arsenicin A: A Natural Adamantane-Type Tetraarsenical Possessing Strong Anti-Acute Promelocytic Leukemia Cell Line Activity|journal=Organometallics|volume=31|issue=5|pages=1808–1816|doi=10.1021/om201180d}} The molecule is chiral, and has been resolved into its two enantiomers. Arsenicin A is active against promyelocytic leukemia cells at lower concentrations than the arsenic(III) oxide drug Trisenox.