Reversine

Reversine
Names

IUPAC name N′-Cyclohexyl-N-(4-morpholinophenyl)-7H-purine-2,6-diamine
Identifiers
CAS Number	656820-32-5^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:70723^N
ChemSpider	182286^N
ECHA InfoCard	100.164.070
MeSH	C484369
PubChem CID	210332
UNII	Z499CLJ023^Y
CompTox Dashboard (EPA)	DTXSID8041113
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
SMILES 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). N verify (what is ^YN ?) Infobox references

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

^ 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.
^ 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.
^ 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.
^ 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.

Henry, Celia (January 5, 2004). "Cellular U-Turn". Chemical and Engineering News. 82 (1): 9. doi:10.1021/cen-v082n001.p009.

CNTs	6-Hydroxy-7-methoxyflavone Adenosine dMeThPmR Estradiol KGO-2142 KGO-2173 MeThPmR Phloridzin Progesterone
ENTs	Barbiturates Benzodiazepines Cilostazol Dilazep Dipyridamole Estradiol Ethanol Hexobendine NBMPR Pentoxifylline Progesterone Propentofylline
PMAT	Decynium-22

XO	Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol Myricetin Niraxostat Oxipurinol Phytic acid Pistacia integerrima Propolis Quercetin Tisopurine Topiroxostat
Others	Aminopterin Azathioprine Methotrexate Mycophenolic acid Pemetrexed Pralatrexate Many others

Others

See also: Receptor/signaling modulators

This page was last edited on 11 December 2023, at 16:32