4-Bromoresveratrol

4-Bromoresveratrol

Identifiers
IUPAC name 5-[(E)-2-(4-bromophenyl)ethenyl]benzene-1,3-diol
CAS Number	1224713-90-9
PubChem CID	18475115
ChemSpider	13447172
ChEMBL	ChEMBL2208038
ECHA InfoCard	100.236.378
Chemical and physical data
Formula	C14H11BrO2
Molar mass	291.144 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1=CC(=CC=C1/C=C/C2=CC(=CC(=C2)O)O)Br
InChI InChI=1S/C14H11BrO2/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h1-9,16-17H/b2-1+ Key:NCJVLKFAQIWASE-OWOJBTEDSA-N

4-Bromoresveratrol is an experimental drug which is a synthetic derivative of the natural product resveratrol, and has been investigated for anti-cancer properties. Unlike resveratrol itself which acts as a sirtuin activator, 4-bromoresveratrol acts as a selective inhibitor of the sirtuin enzymes SIRT1 and SIRT3. In animal models, it inhibits growth of melanomas and inhibited development of cancer stem cells in gastric cancer tissues. ^{[1] [2] [3] [4]}

References

1. Nguyen GT, Gertz M, Steegborn C (November 2013). "Crystal structures of Sirt3 complexes with 4'-bromo-resveratrol reveal binding sites and inhibition mechanism". Chemistry & Biology. 20 (11): 1375–1385. doi:10.1016/j.chembiol.2013.09.019. PMID   24211137.
2. George J, Nihal M, Singh CK, Ahmad N (October 2019). "4'-Bromo-resveratrol, a dual Sirtuin-1 and Sirtuin-3 inhibitor, inhibits melanoma cell growth through mitochondrial metabolic reprogramming". Molecular Carcinogenesis. 58 (10): 1876–1885. doi:10.1002/mc.23080. PMC   6721992 . PMID   31292999.
3. Tai YS, Ma YS, Chen CL, Tsai HY, Tsai CC, Wu MC, et al. (December 2021). "Resveratrol Analog 4-Bromo-Resveratrol Inhibits Gastric Cancer Stemness through the SIRT3-c-Jun N-Terminal Kinase Signaling Pathway". Current Issues in Molecular Biology. 44 (1): 63–72. doi: 10.3390/cimb44010005 . PMC   8929134 . PMID   35723384.
4. Chhabra G, Singh CK, Guzmán-Pérez G, Ndiaye MA, Iczkowski KA, Ahmad N (April 2022). "Antimelanoma Effects of Concomitant Inhibition of SIRT1 and SIRT3 in Braf^V600E/Pten^NULL Mice". The Journal of Investigative Dermatology. 142 (4): 1145–1157.e7. doi:10.1016/j.jid.2021.08.434. PMC   9199498 . PMID   34597611.