ChemicalBook CAS DataBase List 466-75-1

466-75-1

Name	NSC403140
CAS	466-75-1
Molecular Formula	C17H19NO4
MDL Number	MFCD30834689
Molecular Weight	301.337
MOL File	466-75-1.mol

Chemical Properties

storage temp.	Store at -20°C
solubility	DMSO : 100 mg/mL (331.85 mM; Need ultrasonic)
form	Solid
color	White to off-white

Hazard Information

Uses

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].

Definition

ChEBI: Haemanthamine is an alkaloid.

Biological Activity

Haemanthamine is a rhodophylline-like alkaloid isolated from the Amaryllidaceae plant with potent anticancer activity. It targets the ribosome to inhibit protein biosynthesis during the elongation phase of translation, and has proapoptotic, antioxidant, antiviral, antimalarial and anticonvulsant activities.

in vitro

Haemanthamine (1-100 μM; 24-48 hours; A2780 cells) treatment shows a time- and dose-dependent decrease in cell viability.
Haemanthamine (10 μM; 24-72 hours; A2780 cells) treatment leads to a significant inhibition of A2780 cell proliferation.
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.

Cell Viability Assay

< td class="col1"> 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

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.

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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.

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. DOI:10.1016/j.str.2018.01.009
[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. DOI:10.1016/j.phymed.2017.08.019

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