Manzamine A hydrochloride

Manzamine A hydrochloride, a member of the manzamine alkaloids, is a potent, orally active GSK-3β inhibitor (IC50=10.2 μM). Manzamine A hydrochloride shows potent activity against HSV-1 via targeting the viral gene ICP0. Manzamine A hydrochloride targets vacuolar ATPases and inhibits autophagy in pancreatic cancer cells. Manzamine A hydrochloride has antimalarial and anticancer activities.

Product information

CAS Number: 104264-80-4

Molecular Weight: 585.22

Formula: C36H45ClN4O

Chemical Name: (1R,2R,4R,5Z,12R,13S,16Z,22S)-1,4,12-trihydrogenio-25-{9H-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-trien-13-ol hydrochloride

Smiles: Cl.O[C@]12CCC=CCCCC[N@@]3C[C@@]4(C[C@@H]5C=CCCCCN5[C@H]41)[C@@H](CC3)C(=C2)C1N=CC=C2C=1NC1=CC=CC=C12 |c:4,15|

InChiKey: DIVWQABXFSWTEF-YTGAITGWSA-N

InChi: InChI=1S/C36H44N4O.ClH/c41-36-18-10-4-1-2-5-11-20-39-22-17-30(35(25-39)23-26-13-7-3-6-12-21-40(26)34(35)36)29(24-36)32-33-28(16-19-37-32)27-14-8-9-15-31(27)38-33;/h1,4,7-9,13-16,19,24,26,30,34,38,41H,2-3,5-6,10-12,17-18,20-23,25H2;1H/b4-1-,13-7-;/t26-,30-,34+,35-,36-;/m0./s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : 5.88 mg/mL (10.05 mM; Need ultrasonic)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Manzamine A increases acidity in pancreatic cancer cells and non-malignant Vero cells. manzamine A is a potential inhibitor of autophagy by preventing autophagosome turnover. Manzamine A (10 µM; 2 hours; AsPC-1 cells) clearly induced an accumulation of p62 confirming an inhibition of autophagosome turnover. Manzamine A represents an important lead structure for the development of novel antimalarial chemotherapies.

References:

1. Hamann M, et al. Glycogen synthase kinase-3 (GSK-3) inhibitory activity and structure-activity relationship (SAR) studies of the manzamine alkaloids. Potential for Alzheimer's disease. J Nat Prod. 2007;70(9):1397-1405.
2. Kallifatidis G, et al. The marine natural product manzamine A targets vacuolar ATPases and inhibits autophagy in pancreatic cancer cells [published correction appears in Mar Drugs. 2014;12(4):2305-7]. Mar Drugs. 2013;11(9):3500-3516. Published 2013 Sep 17.
3. Winkler JD, et al. Antimalarial activity of a new family of analogues of manzamine A. Org Lett. 2006;8(12):2591-2594.

Products are for research use only. Not for human use.