Sarcophagine

Sarcophagine
Names
	Preferred IUPAC name 3,6,10,13,16,19-Hexazabicyclo[6.6.6]icosane
	Other names Sar chelate
Identifiers
CAS Number	64189-50-0 [ChemSpider];
3D model (JSmol)	Interactive image;
ChemSpider	4908238;
PubChem CID	6394006;
CompTox Dashboard (EPA)	DTXSID30214390;
	InChI InChI=1S/C14H32N6/c1-2-16-8-14-11-19-5-3-17-9-13(7-15-1)10-18-4-6-20-12-14/h13-20H,1-12H2 Key: NVOVSXGZALWAFS-UHFFFAOYSA-N;
	SMILES C1CNCC2CNCCNCC(CN1)CNCCNC2;
Properties
Chemical formula	C14H32N6
Molar mass	284.452 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Sarcophagine (Sar) is a bicyclic cage-like metal chelator molecule^[1] derived from cyclam. Chemical formula of sarcophagine is 3,6,10,13,16,19-hexaazabicyclo(6,6,6)icosane^[2] and additional functional groups are often linked to this structure, such as in DiAmSar (1,8-diamino-Sar). This and many related hexadentate clathrochelates are prepared by template reactions.^[3]

Chemical structure of DiAmSar

Sarcophagine derivatives are used, for example, as ligands in radiopharmaceuticals that require incorporating a radioactive metal cation into an organic and/or biological structure, such as an antibody.^[4]

References

↑ Liu, Shuanglong; Li, Dan; Huang, Chiun-Wei; Yap, Li-Peng; Park, Ryan; Shan, Hong; Li, Zibo; Conti, Peter S. (2012). "The Efficient Synthesis and Biological Evaluation of Novel Bi-Functionalized Sarcophagine for 64Cu Radiopharmaceuticals" (in en). Theranostics 2 (6): 589–596. doi:10.7150/thno.4295. PMID 22737194. PMC 3381345. http://www.thno.org/v02p0589.htm. Retrieved 2017-10-06.
↑ Pubchem. "Diamsar chelate" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/146286.
↑ Gahan, L. R.; Harrowfield, J. M. (2015). "Sepulchrate: Four decades on". Polyhedron 94: 1–51. doi:10.1016/j.poly.2015.03.036.
↑ Liu, Shuanglong; Li, Zibo; Conti, Peter S. (2014-04-03). "Development of Multi-Functional Chelators Based on Sarcophagine Cages" (in en). Molecules 19 (4): 4246–4255. doi:10.3390/molecules19044246. PMID 24705567.

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[1] Liu, Shuanglong; Li, Dan; Huang, Chiun-Wei; Yap, Li-Peng; Park, Ryan; Shan, Hong; Li, Zibo; Conti, Peter S. (2012). "The Efficient Synthesis and Biological Evaluation of Novel Bi-Functionalized Sarcophagine for 64Cu Radiopharmaceuticals" (in en). Theranostics 2 (6): 589–596. doi:10.7150/thno.4295. PMID 22737194. PMC 3381345. http://www.thno.org/v02p0589.htm. Retrieved 2017-10-06.

[2] Pubchem. "Diamsar chelate" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/146286.

[3] Gahan, L. R.; Harrowfield, J. M. (2015). "Sepulchrate: Four decades on". Polyhedron 94: 1–51. doi:10.1016/j.poly.2015.03.036.

[4] Liu, Shuanglong; Li, Zibo; Conti, Peter S. (2014-04-03). "Development of Multi-Functional Chelators Based on Sarcophagine Cages" (in en). Molecules 19 (4): 4246–4255. doi:10.3390/molecules19044246. PMID 24705567.