Manzamine a

Product NameManzamine a
CAS104196-68-1
MFC36H44N4O
MW548.76
EINECS
MOL File104196-68-1.mol

Chemical Properties

Melting point	>240(disassembly)
Boiling point	756.6±60.0 °C(Predicted)
Density	1.26±0.1 g/cm3(Predicted)
storage temp.	-20°
solubility	Soluble in DMSO (up to 25 mg/ml).
pka	13.58±0.40(Predicted)
form	Off white to yellow solid.
color	Off-White to Pale Yellow
optical activity	+5020 (CHCl3)
Stability	Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.

Usage And Synthesis

Description

Manzamine A (104196-68-1) inhibits vacuolar ATPases and inhibits autophagy in pancreatic cancer cells1. Suppresses atherosclerosisin vivo2. Manzamine A displays neuritogenic activity3and suppresses tau hyperphosphorylation in human neuroblastoma cell lines4.

Uses

Manzamine A is a β-Carboline alkaloid with anti-inflammatory.

Definition

ChEBI: An alkaloid of the class of beta-carbolines isolated from Haliclona and Acanthostrongylophora. It exhibits inhibitory activity against Glycogen Synthase Kinase-3 (EC 2.7.11.26).

in vivo

Manzamine A (50 and 100 mol/kg, p.o. or i.p.) inhibits the growth of the rodent malaria parasitePlasmodium berghei in infected mice^[6].
Manzamine A (8 mg/kg, i.p., daily for 8 consecutive days) prolongs the survival of SW mice to 20 days^[7].

Animal Model:	Plasmodium berghei in infected mice^[6]
Dosage:	50 or 100 mol/kg
Administration:	Intraperitoneal injection (i.p.) or oral administration (p.o.)
Result:	Inhibited the growth of the rodent malaria parasite Plasmodium berghei. Prolonged the survival of highly parasitaemic mice.

IC 50

Plasmodium; GSK-3β: 10.2 μM (IC₅₀); CDK5: 1.5 μM (IC₅₀); vacuolar ATPases; Malaria; HSV-1

storage

+4°C

References

[1] GEORGIOS KALLIFATIDIS. The marine natural product manzamine A targets vacuolar ATPases and inhibits autophagy in pancreatic cancer cells.[J]. Marine Drugs, 2013, 11 9: 3500-3516. DOI:10.3390/md11093500
[2] KEISUKE EGUCHI . Manzamine A, a marine-derived alkaloid, inhibits accumulation of cholesterol ester in macrophages and suppresses hyperlipidemia and atherosclerosis in vivo[J]. Bioorganic & Medicinal Chemistry, 2013, 21 13: Pages 3831-3838. DOI:10.1016/j.bmc.2013.04.025
[3] BO ZHANG. Neuritogenic activity-guided isolation of a free base form manzamine A from a marine sponge, Acanthostrongylophora aff. ingens (Thiele, 1899).[J]. Chemical & pharmaceutical bulletin, 2008, 56 6: 866-869. DOI:10.1248/cpb.56.866
[4] MARK HAMANN. Glycogen Synthase Kinase-3 (GSK-3) Inhibitory Activity and Structure–Activity Relationship (SAR) Studies of the Manzamine Alkaloids. Potential for Alzheimer’s Disease[J]. Journal of Natural Products , 2007, 70 9: 1397-1405. DOI:10.1021/np060092r

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