Rebecsinib

Rebecsinib
Identifiers
	IUPAC name (2S,3S,6S,7R,10S,E)-7,10-dihydroxy-2-((2E,4E,6R,7S)-7-hydroxy-7-((2R,3R)-3-((2R,3S)-3-methoxypentan-2-yl)oxiran-2-yl)-6-methylhepta-2,4-dien-2-yl)-3,7-dimethyl-12-oxooxacyclododec-4-en-6-yl acetate;
CAS Number	2598242-04-5;
PubChem CID	9915974;
ChemSpider	8091622;
ChEBI	CHEBI:226528;
Chemical and physical data
Formula	C31H50O9
Molar mass	566.732 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CO[C@@H](CC)[C@@H](C)[C@H]1O[C@@H]1[C@@H](O)[C@H](C)\C=C\C=C(/C)[C@@H]1OC(=O)C[C@H](O)CC[C@@](C)(O)[C@@H](OC(C)=O)\C=C\[C@@H]1C;
	InChI InChI=1S/C31H50O9/c1-9-24(37-8)21(5)29-30(40-29)27(35)18(2)11-10-12-19(3)28-20(4)13-14-25(38-22(6)32)31(7,36)16-15-23(33)17-26(34)39-28/h10-14,18,20-21,23-25,27-30,33,35-36H,9,15-17H2,1-8H3/b11-10+,14-13+,19-12+; Key:LDCZLUDGHYDTHV-FPZDJJGISA-N;

Rebecsinib (17S-FD-895) is an experimental anticancer medication derived by modification of the natural product Pladienolide B, which acts as an inhibitor of splicing-mediated activation of the enzyme ADAR1, and is in development as a potential treatment for leukemia.^[1]^[2]^[3]^[4]^[5]

References

^ Butler MS (September 2013). "Remediating cancer via splicing modulation". Journal of Medicinal Chemistry. 56 (17): 6573–6575. doi:10.1021/jm401289z. PMID 23981063.
^ León B, Kashyap MK, Chan WC, Krug KA, Castro JE, La Clair JJ, et al. (September 2017). "A Challenging Pie to Splice: Drugging the Spliceosome". Angewandte Chemie. 56 (40): 12052–12063. doi:10.1002/anie.201701065. PMC 6311392. PMID 28371109.
^ van der Werf I, Mondala PK, Steel SK, Balaian L, Ladel L, Mason CN, et al. (March 2023). "Detection and targeting of splicing deregulation in pediatric acute myeloid leukemia stem cells". Cell Reports. Medicine. 4 (3): 100962. doi:10.1016/j.xcrm.2023.100962. PMC 10040387. PMID 36889320.
^ Crews LA, Ma W, Ladel L, Pham J, Balaian L, Steel SK, et al. (March 2023). "Reversal of malignant ADAR1 splice isoform switching with Rebecsinib". Cell Stem Cell. 30 (3): 250–263.e6. doi:10.1016/j.stem.2023.01.008. PMC 10134781. PMID 36803553.
^ Murphy LA, Winters AC (December 2023). "Emerging and Future Targeted Therapies for Pediatric Acute Myeloid Leukemia: Targeting the Leukemia Stem Cells". Biomedicines. 11 (12): 3248. doi:10.3390/biomedicines11123248. PMC 10741170. PMID 38137469.

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[1] Butler MS (September 2013). "Remediating cancer via splicing modulation". Journal of Medicinal Chemistry. 56 (17): 6573–6575. doi:10.1021/jm401289z. PMID 23981063.

[2] León B, Kashyap MK, Chan WC, Krug KA, Castro JE, La Clair JJ, et al. (September 2017). "A Challenging Pie to Splice: Drugging the Spliceosome". Angewandte Chemie. 56 (40): 12052–12063. doi:10.1002/anie.201701065. PMC 6311392. PMID 28371109.

[3] van der Werf I, Mondala PK, Steel SK, Balaian L, Ladel L, Mason CN, et al. (March 2023). "Detection and targeting of splicing deregulation in pediatric acute myeloid leukemia stem cells". Cell Reports. Medicine. 4 (3): 100962. doi:10.1016/j.xcrm.2023.100962. PMC 10040387. PMID 36889320.

[4] Crews LA, Ma W, Ladel L, Pham J, Balaian L, Steel SK, et al. (March 2023). "Reversal of malignant ADAR1 splice isoform switching with Rebecsinib". Cell Stem Cell. 30 (3): 250–263.e6. doi:10.1016/j.stem.2023.01.008. PMC 10134781. PMID 36803553.

[5] Murphy LA, Winters AC (December 2023). "Emerging and Future Targeted Therapies for Pediatric Acute Myeloid Leukemia: Targeting the Leukemia Stem Cells". Biomedicines. 11 (12): 3248. doi:10.3390/biomedicines11123248. PMC 10741170. PMID 38137469.

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Identifiers

IUPAC name (2S,3S,6S,7R,10S,E)-7,10-dihydroxy-2-((2E,4E,6R,7S)-7-hydroxy-7-((2R,3R)-3-((2R,3S)-3-methoxypentan-2-yl)oxiran-2-yl)-6-methylhepta-2,4-dien-2-yl)-3,7-dimethyl-12-oxooxacyclododec-4-en-6-yl acetate
CAS Number	2598242-04-5
PubChem CID	9915974
ChemSpider	8091622
ChEBI	CHEBI:226528
Chemical and physical data
Formula	C₃₁H₅₀O₉
Molar mass	566.732 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CO[C@@H](CC)[C@@H](C)[C@H]1O[C@@H]1[C@@H](O)[C@H](C)\C=C\C=C(/C)[C@@H]1OC(=O)C[C@H](O)CC[C@@](C)(O)[C@@H](OC(C)=O)\C=C\[C@@H]1C
InChI InChI=1S/C31H50O9/c1-9-24(37-8)21(5)29-30(40-29)27(35)18(2)11-10-12-19(3)28-20(4)13-14-25(38-22(6)32)31(7,36)16-15-23(33)17-26(34)39-28/h10-14,18,20-21,23-25,27-30,33,35-36H,9,15-17H2,1-8H3/b11-10+,14-13+,19-12+ Key:LDCZLUDGHYDTHV-FPZDJJGISA-N

Rebecsinib

See also

References