SML4090
TH-Z93
≥98% (HPLC)
Synonym(s):
(((4-(Hexyloxy)pyridin-2-yl)amino)methylene)bis(phosphonic acid), P,P′-[[[4-(Hexyloxy)-2-pyridinyl]amino]methylene]bis[phosphonic acid]
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About This Item
Empirical Formula (Hill Notation):
C12H22N2O7P2
CAS Number:
Molecular Weight:
368.26
MDL number:
Quality Level
Assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
soluble (H2O + 1 drop 5M NaOH, 2 mg/mL, clear)
storage temp.
2-8°C
SMILES string
O=P(O)(C(P(O)(O)=O)NC1=NC=CC(OCCCCCC)=C1)O
Biochem/physiol Actions
Potent mevalonate (MVA) pathway farnesyl diphosphate synthase (FPPS) inhibitor that stimulates immune responses in vivo.
TH-Z93 is a potent farnesyl diphosphate synthase (FPPS) inhibitor (IC50 = 90 nM) that stimulates immune responses by blocking the mevalonate (MVA) pathway-mediated post-translational protein geranylgeranylation. When co-administered with antigen in mice in vivo, TH-Z93 triggers strong adjuvant responses, increasing OVA-specific antibody titres (in mice immunized with 100 μg OVA + 100 μg TH-Z93) and protects against death caused by live influenza virus PR8 challenge (in mice immunized with 5 μg PR8 HA1 subunit containing TH-Z93). TH-Z93 adjuvant efficacy is blocked by GGPP and synergized with HMG-CoA inhibitor simvastatin.
TH-Z93 is a potent farnesyl diphosphate synthase (FPPS) inhibitor (IC50 = 90 nM) that stimulates immune responses by blocking the mevalonate (MVA) pathway-mediated post-translational protein geranylgeranylation. When co-administered with antigen in mice in vivo, TH-Z93 triggers strong adjuvant responses, increasing OVA-specific antibody titres (in mice immunized with 100 μg OVA + 100 μg TH-Z93) and protects against death caused by live influenza virus PR8 challenge (in mice immunized with 5 μg PR8 HA1 subunit containing TH-Z93). TH-Z93 adjuvant efficacy is blocked by GGPP and synergized with HMG-CoA inhibitor simvastatin.
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Chenchen Guo et al.
Nature cancer, 3(5), 614-628 (2022-04-23)
Small cell lung cancer (SCLC) lacks effective treatments to overcome chemoresistance. Here we established multiple human chemoresistant xenograft models through long-term intermittent chemotherapy, mimicking clinically relevant therapeutic settings. We show that chemoresistant SCLC undergoes metabolic reprogramming relying on the mevalonate
Yun Xia et al.
Cell, 175(4), 1059-1073 (2018-10-03)
Motivated by the clinical observation that interruption of the mevalonate pathway stimulates immune responses, we hypothesized that this pathway may function as a druggable target for vaccine adjuvant discovery. We found that lipophilic statin drugs and rationally designed bisphosphonates that
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