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Merck
CN

SML4208

STING agonist C53

≥98% (HPLC), powder, STING agonist

Synonym(s):

1-[(2-Chloro-6-fluorophenyl)methyl]-2,3-dihydro-3,3-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-1H-indole-6-carboxamide, hSTING agonist C53, C53

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About This Item

Empirical Formula (Hill Notation):
C25H19ClF4N2O2
CAS Number:
Molecular Weight:
490.88
MDL number:
NACRES:
NA.21
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
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SMILES string

O=C(C1=CC=C2C(N(CC3=C(Cl)C=CC=C3F)C(C2(C)C)=O)=C1)NCC4=C(F)C=C(F)C=C4F

Quality Level

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

-10 to -25°C

Application

STING agonist C53 may be used: in promoting STING activation by binding to cryptic pocket in its transmembrane domain, enhancing oligomerization, immune signaling and in antitumor response.

Biochem/physiol Actions

STING agonist C53 (Compound 53), is a potent STING agonist with an EC50 of 185 nM for human STING activation. C53 modestly promotes STING oligomerization by binding to the transmembrane domain (TMD), acting orthogonally to cGAMP, which binds to the ligand-binding domain (LBD). In combination with cGAMP, C53 enhances STING activation (EC50 of 100 nM) and further promotes oligomerization, leading to stronger phosphorylation of STING, TANK-binding kinase 1 (TBK1), and interferon regulatory factor 3 (IRF3) than either compound alone. Uniquely, C53 also inhibits STING′s proton channel activity in the Golgi, blocking processes such as microtubule-associated protein 1A/1B light chain 3 beta (LC3B) lipidation and nucleotide-binding domain, leucine-rich–containing family, pyrin domain–containing-3 (NLRP3) inflammasome activation, while preserving its ability to induce interferon production. Although C53 activates human STING efficiently, it is inactive against mouse STING. In in vivo studies, C53 induces cytokine production and dendritic cell maturation, with increased expression of activation markers CD86 and CD83.

Regulatory Information

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Bingxu Liu et al.
Science (New York, N.Y.), 381(6657), 508-514 (2023-08-03)
Proton leakage from organelles is a common signal for noncanonical light chain 3B (LC3B) lipidation and inflammasome activation, processes induced upon stimulator of interferon genes (STING) activation. On the basis of structural analysis, we hypothesized that human STING is a
Defen Lu et al.
Nature, 604(7906), 557-562 (2022-04-08)
Stimulator of interferon genes (STING) is an adaptor protein in innate immunity against DNA viruses or bacteria1-5. STING-mediated immunity could be exploited in the development of vaccines or cancer immunotherapies. STING is a transmembrane dimeric protein that is located in
Sourav Basu et al.
European journal of medicinal chemistry, 229, 114087-114087 (2022-01-09)
STING mediates innate immune responses that are triggered by the presence of cytosolic DNA. Activation of STING to boost antigen recognition is a therapeutic modality that is currently being tested in cancer patients using nucleic-acid based macrocyclic STING ligands. We

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