Manzamine A hydrochloride

• CAT Number: I045552
• CAS Number: 104264-80-4
• Molecular Formula: C36H45ClN4O
• Molecular Weight: 585.22
• Purity: ≥95%
• Synonyms: (1R,2R,4R,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;hydrochloride
• 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
• InChIKey: DIVWQABXFSWTEF-YTGAITGWSA-N
• SMILES: C1CCN2CCC3C(=CC(CCC=CC1)(C4C3(C2)CC5N4CCCCC=C5)O)C6=NC=CC7=C6NC8=CC=CC=C78.Cl

Manzamine A hydrochloride (Cat No.: I045552) is a marine-derived β-carboline alkaloid isolated from sponges, notable for its diverse antitumor, antimicrobial, antimalarial, and antiviral activities. It disrupts multiple cellular pathways, including inhibition of glycogen synthase kinase-3β (GSK-3β) and modulation of autophagy, contributing to its anticancer potential. Manzamine A also shows efficacy against Plasmodium spp. and certain viruses, highlighting its broad pharmacological profile. The hydrochloride salt form enhances solubility and stability, making it suitable for laboratory use. It serves as a valuable tool in natural product drug discovery.

Reference

[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.
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[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.
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[3]. Winkler JD, et al. Antimalarial activity of a new family of analogues of manzamine A. Org Lett. 2006;8(12):2591-2594.
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[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.
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[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.
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[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.
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[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.
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