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Merck

SML2061

ST1926

≥98% (HPLC)

Synonym(s):

(2E)-3-(4′-Hydroxy-3′-tricyclo[3.3.1.13,7]dec-1-yl[1,1′-biphenyl]-4-yl)-2-propenoic acid, Adarotene, ST 1926

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About This Item

Empirical Formula (Hill Notation):
C25H26O3
CAS Number:
496868-77-0
Molecular Weight:
374.47
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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Product Name

ST1926, ≥98% (HPLC)

SMILES string

Oc1c(cc(cc1)c5ccc(cc5)\C=C\C(=O)O)C32CC4CC(C3)CC(C2)C4

InChI key

QAWBIEIZDDIEMW-FPYGCLRLSA-N

InChI

1S/C25H26O3/c26-23-7-6-21(20-4-1-16(2-5-20)3-8-24(27)28)12-22(23)25-13-17-9-18(14-25)11-19(10-17)15-25/h1-8,12,17-19,26H,9-11,13-15H2,(H,27,28)/b8-3+

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Biochem/physiol Actions

ST1926 is an atypical retinoid that is able to overcome resistance to ATRA. ST1926 appears to induce apoptosis by production of DNA double-strand breaks (DSB) and chromosomal lesions during the S phase of the cell cycle.
ST1926 is considered to be more apoptotic than CD437. It is much effective in mobilizing calcium than CD437. ST1926 repress toll-like receptor 4 (TLR4)/myeloid differentiation factor 88 (MyD88) signal pathway to disable the actions of nuclear factor-κB (NF-κB). It has the ability to repress inflammation response and ROS synthesis in lung epithelial cells in vitro.
atypical retinoid

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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ST1926, a novel and orally active retinoid-related molecule inducing apoptosis in myeloid leukemia cells: modulation of intracellular calcium homeostasis
Garattini E et al.
Blood, 103(1), 194-207 (2004)
Valentina Zuco et al.
International journal of cancer, 126(5), 1246-1255 (2009-08-14)
The synthetic atypical retinoids containing an adamantyl group exhibit antiproliferative or proapoptotic activities. Apoptosis induction is a dose-dependent effect independent of retinoid receptors. We have reported that induction of apoptosis by the atypical retinoid, ST1926, is associated with early manifestations
Accelerated inflammation and oxidative stress induced by LPS in acute lung injury: Inhibition by ST1926
Dong Z and Yuan Y
International Journal of Molecular Medicine, 41(6), 3405-3421 (2018)
Edoardo Parrella et al.
Molecular pharmacology, 70(3), 909-924 (2006-06-22)
The retinoid-related molecules (RRMs) ST1926 [(E)-3-(4'-hydroxy-3'-adamantylbiphenyl-4-yl)acrylic acid] and CD437 (6-[3-(1-adamantyl)-4-hydroxyphenyl]-2-naphthalene carboxylic acid) are promising anticancer agents. We compared the retinoic acid receptor (RAR) trans-activating properties of the two RRMs and all-trans-retinoic acid (ATRA). ST1926 and CD437 are better RARgamma agonists
Leeanna El-Houjeiri et al.
Molecular cancer therapeutics, 16(10), 2047-2057 (2017-06-18)
Acute myeloid leukemia (AML) is one of the most frequent types of blood malignancies. It is a complex disorder of undifferentiated hematopoietic progenitor cells. The majority of patients generally respond to intensive therapy. Nevertheless, relapse is the major cause of

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