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466-75-1

466-75-1 structure
466-75-1 structure
  • Name: Haemanthamine
  • Chemical Name: Haemanthamin
  • CAS Number: 466-75-1
  • Molecular Formula: C17H19NO4
  • Molecular Weight: 301.33700
  • Catalog: Signaling Pathways Anti-infection Influenza Virus
  • Create Date: 2017-12-16 17:30:58
  • Modify Date: 2024-01-09 20:53:12
  • Haemanthamine is a crinine-type alkaloid isolated from the Amaryllidaceae plants with potent anticancer activity. Haemanthamine targets ribosomal that inhibits protein biosynthesis during the elongation stage of translation. Haemanthamine has pro-apoptotic, antioxidant, antiviral, antimalarial and anticonvulsant activities[1][2].

Name Haemanthamin
Synonyms Epihaemanthamin
Haemanthanin
Natalensin
3-Epicrinamine
Natalensine
Description Haemanthamine is a crinine-type alkaloid isolated from the Amaryllidaceae plants with potent anticancer activity. Haemanthamine targets ribosomal that inhibits protein biosynthesis during the elongation stage of translation. Haemanthamine has pro-apoptotic, antioxidant, antiviral, antimalarial and anticonvulsant activities[1][2].
Related Catalog
In Vitro Haemanthamine (1-100 µM; 24-48 hours; A2780 cells) treatment shows a time- and dose-dependent decrease in cell viability[2]. Haemanthamine (10 µM; 24-72 hours; A2780 cells) treatment leads to a significant inhibition of A2780 cell proliferation[2]. Haemanthamine binds at the A-site cleft of the peptidyl transferase center on the large ribosomal subunit, creating unique molecular interactions with the 25S rRNA. Haemanthamine has a highly specific inhibitory effect on pre-rRNA processing, leading to the activation of a p53-dependent antitumoral surveillance pathway known as nucleolar stress[1]. Cell Viability Assay[2] Cell Line: A2780 ovarian cancer cells Concentration: 1 µM, 10 µM, 50 µM, 100 µM Incubation Time: 24 hours, 48 hours Result: Showed a time- and dose-dependent decrease in cell viability. Cell Proliferation Assay[2] Cell Line: A2780 ovarian cancer cells Concentration: 10 µM Incubation Time: 24 hours, 48 hours, 72 hours Result: Led to a significant inhibition of A2780 cell proliferation.
In Vivo A pharmacokinetic study of Haemanthamine in rats shows a rapid distribution phase of 30 min, a half-life of 70.4 min, and a major clearance through renal elimination. The high distribution volume of 13.7 L/kg suggests a high intracellular penetration, and its plasmatic concentration remains higher than 1 μM for at least 1 hr after a single 10-mg/kg administration[1].
References

[1]. Pellegrino S, et al. The Amaryllidaceae Alkaloid Haemanthamine Binds the Eukaryotic Ribosome to Repress Cancer Cell Growth. Structure. 2018 Mar 6;26(3):416-425.e4.

[2]. Seifrtová M, et al. Haemanthamine alters sodium butyrate-induced histone acetylation, p21WAF1/Cip1 expression, Chk1 and Chk2 activation and leads to increased growth inhibition and death in A2780 ovarian cancer cells. Phytomedicine. 2017 Nov 15;35:1-10.

Density 1.42g/cm3
Boiling Point 467.5ºC at 760 mmHg
Molecular Formula C17H19NO4
Molecular Weight 301.33700
Flash Point 236.5ºC
Exact Mass 301.13100
PSA 51.16000
LogP 1.12460
Vapour Pressure 1.53E-09mmHg at 25°C
Index of Refraction 1.679
Storage condition -20°C
Precursor  0

DownStream  1