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Reversine

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]

Reversine
Names
IUPAC name
N-Cyclohexyl-N-(4-morpholinophenyl)-7H-purine-2,6-diamine
Identifiers
  • 656820-32-5 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:70723 N
ChemSpider
  • 182286 N
ECHA InfoCard 100.164.070
MeSH C484369
  • 210332
UNII
  • Z499CLJ023 Y
  • DTXSID8041113
  • 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 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 ?)

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 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

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

reversine, morpholinoanilino, cyclohexylaminopurine, small, molecule, developed, group, peter, schultz, used, stem, cell, dedifferentiation, names, iupac, name, cyclohexyl, morpholinophenyl, purine, diamine, identifiers, number, 656820, model, jsmol, interacti. 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 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 NKey ZFLJHSQHILSNCM UHFFFAOYSA N NInChI 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 C 21H 27N 7O 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 Y N Infobox references 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 edit 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 External links editHenry Celia January 5 2004 Cellular U Turn Chemical and Engineering News 82 1 9 doi 10 1021 cen v082n001 p009 Retrieved from https en wikipedia org w index php title Reversine amp oldid 1189403425, wikipedia, wiki, book, books, library,

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