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Manzamine A

Manzamine A

Product ID M0255
Cas No. 104196-68-1
Purity ≥98%
Product Unit SizeCostQuantityStock
1 mg $337.40 In stock
5 mg $1,230.70 Please Inquire
10 mg $1,795.80 Please Inquire
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  • Description
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Description

Manzamine A is an alkaloid found in marine sponges. Manzamine A exhibits neuroprotective, anticancer, anti-hyperlipidemic, anti-atherosclerotic, antibiotic, and antiviral activities. In vitro, manzamine A uncouples vacuolar ATPases, inhibiting autophagy and tumor growth. Manzamine A inhibits foam cell formation in macrophages, a hallmark of atherosclerosis. Additionally, manzamine A inhibits cholesterol ester formation and acyl-CoA:cholesterol acyl-transferase (ACAT) activity in vitro and decreases total cholesterol, triglycerides, and LDL levels in vivo. This compound displays antibacterial activity against gram positive and gram negative bacteria; it may also exhibit anti-parasitic activity. In corneal cells, manzamine A inhibits viral replication and infection of herpes simplex virus a (HSV-1), inhibiting HSV-1 virion host shutoff activity. In neuroblastoma cells, manzamine A displays potential benefit in the treatment of Alzheimer’s disease by decreasing tau hyperphosphorylation and inhibiting glycogen synthase kinase 3 (GSK3).

Product Info

Cas No.

104196-68-1

Purity

≥98%

Formula

C36H44N4O

Formula Wt.

548.76

Chemical Name

(1R,2R,5Z,12R,13S,16Z)-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

IUPAC Name

(1R,2R,5Z,12R,13S,16Z)-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

Synonym

Keramamine A

Appearance

White Crystal Powder

Shipping and Storage

Store Temp

-20°C

Ship Temp

Ambient

Downloads

MSDS

M0255 MSDS PDF

Info Sheet

M0255 Info Sheet PDF

References

Lin LC, Kuo TT, Chang HY, et al. Manzamine A Exerts Anticancer Activity against Human Colorectal Cancer Cells. Mar Drugs. 2018 Jul 29;16(8):252. doi: 10.3390/md16080252. PMID: 30060617.

Guzmán EA, Johnson JD, Linley PA, et. al. A novel activity from an old compound: Manzamine A reduces the metastatic potential of AsPC-1 pancreatic cancer cells and sensitizes them to TRAIL-induced apoptosis.
Invest New Drugs. 2011 Oct;29(5):777-85. doi: 10.1007/s10637-010-9422-6. Epub 2010 Mar 30. PMID: 20352293

Kallifatidis G, Hoepfner D, Jaeg T, et al. The marine natural product manzamine A targets vacuolar ATPases and inhibits autophagy in pancreatic cancer cells. Mar Drugs. 2013 Sep 17;11(9):3500-16. PMID: 24048269.

Eguchi K, Fujiwara Y, Hayashida A, et al. Manzamine A, a marine-derived alkaloid, inhibits accumulation of cholesterol ester in macrophages and suppresses hyperlipidemia and atherosclerosis in vivo. Bioorg Med Chem. 2013 Jul 1;21(13):3831-8. PMID: 23665143.

Aqil F, Zahin M, El Sayed KA, et al. Antimicrobial, antioxidant, and antimutagenic activities of selected marine natural products and tobacco cembranoids. Drug Chem Toxicol. 2011 Apr;34(2):167-79. PMID: 21314466.

Palem JR, Bedadala GR, El Sayed KA, et al. Manzamine A as a novel inhibitor of herpes simplex virus type-1 replication in cultured corneal cells. Planta Med. 2011 Jan;77(1):46-51. PMID: 20645244.

Hamann M, Alonso D, Martín-Aparicio E, 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 Sep;70(9):1397-405. PMID: 17708655.

Winkler JD, Londregan AT, Hamann MT. Antimalarial activity of a new family of analogues of manzamine A. Org Lett. 2006 Jun 8;8(12):2591-4. PMID: 16737321.

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