Arotinoid acid

Arotinoid acid

Identifiers
IUPAC name 4-[(E)-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-1-enyl]benzoic acid
CAS Number	71441-28-6
PubChem CID	5289501
DrugBank	DB02877
UNII	673M8C29UR
KEGG	C15634
ChEBI	CHEBI:75261
ChEMBL	ChEMBL275311
CompTox Dashboard (EPA)	DTXSID6040743
ECHA InfoCard	100.150.879
Chemical and physical data
Formula	C24H28O2
Molar mass	348.486 g·mol−1
3D model (JSmol)	Interactive image
SMILES C/C(=C\C1=CC=C(C=C1)C(=O)O)/C2=CC3=C(C=C2)C(CCC3(C)C)(C)C
InChI InChI=1S/C24H28O2/c1-16(14-17-6-8-18(9-7-17)22(25)26)19-10-11-20-21(15-19)24(4,5)13-12-23(20,2)3/h6-11,14-15H,12-13H2,1-5H3,(H,25,26)/b16-14+ Key:FOIVPCKZDPCJJY-JQIJEIRASA-N

Arotinoid acid (TTNPB, Ro 13-7410) is an experimental drug which is a synthetic retinoid derivative. It was originally developed for potential medical applications in cancer treatment, but was not adopted due to potent teratogenic activity. However it has since been found to be useful as part of a cocktail of signalling factors used for cellular reprogramming in order to produce pluripotent stem cells. ^{[1] [2] [3]}

References

1. Pignatello MA, Kauffman FC, Levin AA (September 1999). "Multiple factors contribute to the toxicity of the aromatic retinoid TTNPB (Ro 13-7410): interactions with the retinoic acid receptors". Toxicology and Applied Pharmacology. 159 (2): 109–116. Bibcode:1999ToxAP.159..109P. doi:10.1006/taap.1999.8726. PMID   10495774.
2. Hu Y, Yang Y, Tan P, Zhang Y, Han M, Yu J, et al. (May 2023). "Induction of mouse totipotent stem cells by a defined chemical cocktail". Nature. 617 (7962): 792–797. Bibcode:2023Natur.617..792H. doi:10.1038/s41586-022-04967-9. PMID   35728625.
3. Nath SC, Babaei-Abraki S, Meng G, Heale KA, Hsu CY, Rancourt DE (February 2024). "A retinoid analogue, TTNPB, promotes clonal expansion of human pluripotent stem cells by upregulating CLDN2 and HoxA1". Communications Biology. 7 (1): 190. doi:10.1038/s42003-024-05812-7. PMC   10873380 . PMID   38365890.