Reversine

Reversine
Names
IUPAC name
N′-Cyclohexyl-N-(4-morpholinophenyl)-7H-purine-2,6-diamine
Identifiers
CAS Number
  • 656820-32-5 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:70723 ☒N
ChemSpider
  • 182286 ☒N
ECHA InfoCard 100.164.070 Edit this at Wikidata
MeSH C484369
PubChem CID
  • 210332
UNII
  • Z499CLJ023 checkY
CompTox Dashboard (EPA)
  • DTXSID8041113 Edit this at Wikidata
InChI
  • 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
Chemical formula
 C21H27N7O
Molar mass 393.495 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Chemical compound

Reversine, or 2-(4-morpholinoanilino)-6-cyclohexylaminopurine, is a small molecule developed by the group of Peter G. Schultz, used for stem cell dedifferentiation.[1][2]

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

Reversine is known to act as an antagonist of the adenosine A3 receptor. Reversine is a potent inhibitor of the mitotic kinase Mps1[4] and it is widely used to study the process of chromosome segregation.

References

  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

  • Henry, Celia (January 5, 2004). "Cellular U-Turn". Chemical and Engineering News. 82 (1): 9. doi:10.1021/cen-v082n001.p009.
  • v
  • t
  • e
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
See also: Receptor/signaling modulators