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Hesperadin
Names
Preferred IUPAC name
N -[(3Z )-2-Oxo-3-(phenyl{4-[(piperidin-1-yl)methyl]anilino}methylidene)-2,3-dihydro-1H -indol-5-yl]ethanesulfonamide
Identifiers
ChemSpider
UNII
InChI=1S/C29H32N4O3S/c1-2-37(35,36)32-24-15-16-26-25(19-24)27(29(34)31-26)28(22-9-5-3-6-10-22)30-23-13-11-21(12-14-23)20-33-17-7-4-8-18-33/h3,5-6,9-16,19,30,32H,2,4,7-8,17-18,20H2,1H3,(H,31,34)/b28-27-
N Key: GLDSKRNGVVYJAB-DQSJHHFOSA-N
N InChI=1/C29H32N4O3S/c1-2-37(35,36)32-24-15-16-26-25(19-24)27(29(34)31-26)28(22-9-5-3-6-10-22)30-23-13-11-21(12-14-23)20-33-17-7-4-8-18-33/h3,5-6,9-16,19,30,32H,2,4,7-8,17-18,20H2,1H3,(H,31,34)/b28-27-
Key: GLDSKRNGVVYJAB-DQSJHHFOBF
CCS(=O)(=O)NC1=CC2=C(C=C1)NC(=O)C2=C(C3=CC=CC=C3)NC4=CC=C(C=C4)CN5CCCCC5
Properties
C 29 H 32 N 4 O 3 S
Molar mass
516.66 g·mol−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Hesperadin is an
aurora kinase inhibitor .
The small molecule inhibits
chromosome alignment and segregation by limiting the function of
mitotic kinases
Aurora B and
Aurora A . Hesperadin causes cells to enter
anaphase much faster, sometimes before the chromosomes are properly bi-oriented.
[1]
Hesperadin, like other miotic inhibitors, limits and sometimes can stop the process of mitosis in
cells . For this reason, some have considered hesperadin's potential as a
cancer -preventing drug.
[2]
Hesperadin works as an
inhibitor , attaching to the active sites of Aurora A and Aurora B kinases.
[2]
References
^ Hauf, Silke; Cole, Richard W.; LaTerra, Sabrina; Zimmer, Christine; Schnapp, Gisela; Walter, Rainer; Heckel, Armin; van Meel, Jacques; Rieder, Conly L. (2003-04-28).
"The small molecule Hesperadin reveals a role for Aurora B in correcting kinetochore-microtubule attachment and in maintaining the spindle assembly checkpoint" . The Journal of Cell Biology . 161 (2): 281–294.
doi :
10.1083/jcb.200208092 .
ISSN
0021-9525 .
PMC
2172906 .
PMID
12707311 .
^
a
b Jetton, Neal; Rothberg, Karen G.; Hubbard, James G.; Wise, John; Li, Yan; Ball, Haydn L.; Ruben, Larry (April 2009).
"The cell cycle as a therapeutic target againstTrypanosoma brucei: Hesperadin inhibits Aurora kinase-1 and blocks mitotic progression in bloodstream forms" . Molecular Microbiology . 72 (2): 442–458.
doi :
10.1111/j.1365-2958.2009.06657.x .
ISSN
0950-382X .
PMC
2697958 .
PMID
19320832 .