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Reversine

From Wikipedia, the free encyclopedia
Reversine
Names
IUPAC name
N-Cyclohexyl-N-(4-morpholinophenyl)-7H-purine-2,6-diamine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard100.164.070Edit this at Wikidata
MeSHC484369
UNII
  • InChI=1S/C21H27N7O/c1-2-4-15(5-3-1)24-20-18-19(23-14-22-18)26-21(27-20)25-16-6-8-17(9-7-16)28-10-12-29-13-11-28/h6-9,14-15H,1-5,10-13H2,(H3,22,23,24,25,26,27) ☒N
    Key: ZFLJHSQHILSNCM-UHFFFAOYSA-N ☒N
  • InChI=1/C21H27N7O/c1-2-4-15(5-3-1)24-20-18-19(23-14-22-18)26-21(27-20)25-16-6-8-17(9-7-16)28-10-12-29-13-11-28/h6-9,14-15H,1-5,10-13H2,(H3,22,23,24,25,26,27)
    Key: ZFLJHSQHILSNCM-UHFFFAOYAD
  • C1CCC(CC1)NC2=NC(=NC3=C2NC=N3)NC4=CC=C(C=C4)N5CCOCC5
Properties
C21H27N7O
Molar mass393.495 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Reversine, or2-(4-morpholinoanilino)-6-cyclohexylaminopurine, is a small molecule developed by the group ofPeter G. Schultz, used forstem celldedifferentiation.[1][2]

It also has the potential to selectively induce cell death in cancer cells.[3]

Reversine is known to act as anantagonist of theadenosineA3 receptor. Reversine is a potent inhibitor of the mitotic kinase Mps1[4] and it is widely used to study the process ofchromosome segregation.

References

[edit]
  1. ^Chen, Shuibing; Zhang, Qisheng; Wu, Xu; Schultz, Peter G.; Ding, Sheng (2004). "Dedifferentiation of Lineage-Committed Cells by a Small Molecule".Journal of the American Chemical Society.126 (2):410–1.doi:10.1021/ja037390k.PMID 14719906.
  2. ^Chen, S.; Takanashi, S.; Zhang, Q.; Xiong, W.; Zhu, S.; Peters, E. C.; Ding, S.; Schultz, P. G. (2007)."Reversine increases the plasticity of lineage-committed mammalian cells".Proceedings of the National Academy of Sciences.104 (25):10482–7.Bibcode:2007PNAS..10410482C.doi:10.1073/pnas.0704360104.PMC 1965539.PMID 17566101.
  3. ^Piccoli, Marco; Palazzolo, Giacomo; Conforti, Erika; Lamorte, Giuseppe; Papini, Nadia; Creo, Pasquale; Fania, Chiara; Scaringi, Raffaella; Bergante, Sonia; Tringali, Cristina; Roncoroni, Leda; Mazzoleni, Stefania; Doneda, Luisa; Galli, Rossella; Venerando, Bruno; Tettamanti, Guido; Gelfi, Cecilia; Anastasia, Luigi (2012)."The synthetic purine reversine selectively induces cell death of cancer cells".Journal of Cellular Biochemistry.113 (10):3207–17.doi:10.1002/jcb.24197.PMID 22615034.S2CID 2741461.
  4. ^Santaguida, Stefano; Tighe, Anthony; D'Alise, Anna Morena; Taylor, Stephen S.; Musacchio, Andrea (2010-07-12)."Dissecting the role of MPS1 in chromosome biorientation and the spindle checkpoint through the small molecule inhibitor reversine".The Journal of Cell Biology.190 (1):73–87.doi:10.1083/jcb.201001036.ISSN 1540-8140.PMC 2911657.PMID 20624901.

External links

[edit]
Receptor
(ligands)
P0 (adenine)
P1
(adenosine)
P2
(nucleotide)
P2X
(ATPTooltip Adenosine triphosphate)
P2Y
Transporter
(blockers)
CNTsTooltip Concentrative nucleoside transporters
ENTsTooltip Equilibrative nucleoside transporters
PMATTooltip Plasma membrane monoamine transporter
Enzyme
(inhibitors)
XOTooltip Xanthine oxidase
Others
Others
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