ML221

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ML221
Identifiers
  • 4-oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate
CAS Number
PubChem CID
Chemical and physical data
FormulaC17H11N3O6S
Molar mass385.35 g·mol−1
3D model (JSmol)
  • C1=CN=C(N=C1)SCC2=CC(=O)C(=CO2)OC(=O)C3=CC=C(C=C3)[N+](=O)[O-]
  • InChI=1S/C17H11N3O6S/c21-14-8-13(10-27-17-18-6-1-7-19-17)25-9-15(14)26-16(22)11-2-4-12(5-3-11)20(23)24/h1-9H,10H2
  • Key:UASIRTUMPRQVFY-UHFFFAOYSA-N

ML221 is a drug which is a selective, small-molecule antagonist for the apelin receptor. It is primarily used for research into the function of this receptor pathway, but also has potential medical applications.[1][2][3][4][5][6][7][8][9]

References

[edit]
  1. ^ Maloney PR, Khan P, Hedrick M, Gosalia P, Milewski M, Li L, et al. (November 2012). "Discovery of 4-oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate (ML221) as a functional antagonist of the apelin (APJ) receptor". Bioorganic & Medicinal Chemistry Letters. 22 (21): 6656–6660. doi:10.1016/j.bmcl.2012.08.105. PMC 3729231. PMID 23010269.
  2. ^ Hall C, Ehrlich L, Venter J, O'Brien A, White T, Zhou T, et al. (February 2017). "Inhibition of the apelin/apelin receptor axis decreases cholangiocarcinoma growth". Cancer Letters. 386: 179–188. doi:10.1016/j.canlet.2016.11.025. PMC 5510601. PMID 27894959.
  3. ^ Rak A, Drwal E, Rame C, Knapczyk-Stwora K, Słomczyńska M, Dupont J, et al. (July 2017). "Expression of apelin and apelin receptor (APJ) in porcine ovarian follicles and in vitro effect of apelin on steroidogenesis and proliferation through APJ activation and different signaling pathways". Theriogenology. 96: 126–135. doi:10.1016/j.theriogenology.2017.04.014. PMID 28532828.
  4. ^ Ishimaru Y, Shibagaki F, Yamamuro A, Yoshioka Y, Maeda S (November 2017). "An apelin receptor antagonist prevents pathological retinal angiogenesis with ischemic retinopathy in mice". Scientific Reports. 7 (1) 15062. Bibcode:2017NatSR...715062I. doi:10.1038/s41598-017-15602-3. PMC 5678128. PMID 29118394.
  5. ^ Neelakantan D, Dogra S, Devapatla B, Jaiprasart P, Mukashyaka MC, Janknecht R, et al. (June 2019). "Multifunctional APJ Pathway Promotes Ovarian Cancer Progression and Metastasis". Molecular Cancer Research. 17 (6): 1378–1390. doi:10.1158/1541-7786.MCR-18-0989. PMC 6548659. PMID 30858172.
  6. ^ Song K, Yang X, An G, Xia X, Zhao J, Xu X, et al. (November 2022). "Targeting APLN/APJ restores blood-testis barrier and improves spermatogenesis in murine and human diabetic models". Nature Communications. 13 (1) 7335. Bibcode:2022NatCo..13.7335S. doi:10.1038/s41467-022-34990-3. PMC 9705293. PMID 36443325.
  7. ^ Das M, Gurusubramanian G, Roy VK (October 2023). "Apelin receptor antagonist (ML221) treatment has a stimulatory effect on the testicular proliferation, antioxidants system and steroidogenesis in adult mice". Neuropeptides. 101 102354. doi:10.1016/j.npep.2023.102354. PMID 37379791.
  8. ^ Wang Q, Wang B, Zhang W, Zhang T, Liu Q, Jiao X, et al. (May 2024). "APLN promotes the proliferation, migration, and glycolysis of cervical cancer through the PI3K/AKT/mTOR pathway". Archives of Biochemistry and Biophysics. 755 109983. doi:10.1016/j.abb.2024.109983. PMID 38561035.
  9. ^ Bist G, Elsheikh A, Kim S, Huang RY, Ruszaj D, Woo S, et al. (December 2025). "Novel small molecule analogs for advancing apelin receptor antagonism with enhanced plasma and microsomal stability". Bioorganic & Medicinal Chemistry Letters. 129 130367. doi:10.1016/j.bmcl.2025.130367. PMID 40784515.
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