Manzamine A

Manzamine A, an orally active beta-carboline alkaloid, inhibits specifically GSK-3β and CDK-5 with IC50s of 10.2 μM and 1.5 μM, respectively. Manzamine A targets vacuolar ATPases and inhibits autophagy in pancreatic cancer cells. Manzamine A has antimalarial and anticancer activities. Manzamine A also shows potent activity against HSV-1[1][2][3][4].

Product Specifications

CAS Number

[104196-68-1]

Product Name Alternative

Keramamine A

UNSPSC

12352005

Hazard Statement

H302

Target

Autophagy; CDK; GSK-3; HSV; Parasite; Proton Pump

Type

Natural Products

Related Pathways

Anti-infection; Autophagy; Cell Cycle/DNA Damage; Membrane Transporter/Ion Channel; PI3K/Akt/mTOR; Stem Cell/Wnt

Applications

COVID-19-anti-virus

Field of Research

Cancer; Infection; Neurological Disease

Assay Protocol

https://www.medchemexpress.com/manzamine-a.html

Purity

98.2

Solubility

DMSO : 10 mg/mL (ultrasonic)

Smiles

O[C@]1(CC/C=C\CCCC2)[C@@]3([H])[C@@](C[C@@]4([H])N3CCCC/C=C\4)(C[N@@]2CC5)[C@]5([H])C(C6=C(NC7=CC=CC=C87)C8=CC=N6)=C1

Molecular Formula

C36H44N4O

Molecular Weight

548.76

Precautions

H302

References & Citations

[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. |[4]Palem JR, et al. Manzamine A as a novel inhibitor of herpes simplex virus type-1 replication in cultured corneal cells. Planta Med. 2011;77 (1) :46-51. |[5]Wahba AE, et al. Structure-activity relationship studies of manzamine A: amidation of positions 6 and 8 of the beta-carboline moiety. Bioorg Med Chem. 2009 Nov 15;17 (22) :7775-82. |[6]Donia M, et al. Marine natural products and their potential applications as anti-infective agents. Lancet Infect Dis. 2003 Jun;3 (6) :338-48. |[7]El Sayed KA, et al. New manzamine alkaloids with potent activity against infectious diseases. J Am Chem Soc. 2001 Mar 7;123 (9) :1804-8.