Manzamine A
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MedKoo CAT#: 540279

CAS#: 104196-68-1

Description: Manzamine A is a vacuolar ATPase uncoupler and GSK-3 inhibitor found in marine sponges. It inhibits autophagy and tumor growth in cancer models, suppresses foam cell formation in macrophages, prevents growth of gram positive and gram negative bacteria, and decreases tau hyperphosphorylation.

Chemical Structure

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Manzamine A
CAS# 104196-68-1
Instruction

Theoretical Analysis

MedKoo Cat#: 540279
Name: Manzamine A
CAS#: 104196-68-1
Chemical Formula: C36H44N4O
Exact Mass: 548.35
Molecular Weight: 548.770
Elemental Analysis: C, 78.79; H, 8.08; N, 10.21; O, 2.92

Price and Availability

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1mg USD 450 2 weeks
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Synonym: Keramamine A; Manzamine A;

IUPAC/Chemical Name: (1R,4S,9Z,13S,13aR,20aR,21aR)-2,3,5,6,7,8,11,12,15,16,17,18,20a,21-tetradecahydro-24-(9H-pyrido[3,4-b]indol-1-yl)-1,13-etheno-4,21a-methano-1H-azocino[1',2':1,5]pyrrolo[3,2-e]azacyclopentadecin-13(13aH)-ol

InChi Key: FUCSLKWLLSEMDQ-SHIWRGCWSA-N

InChi Code: InChI=1S/C36H44N4O/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/b4-1+,13-7-/t26-,30-,34+,35-,36-/m0/s1

SMILES Code: [H][C@@]1(N2CCCC/C=C\1)C[C@@]3(C4)[C@]2([H])[C@]5(O)CC/C=C/CCCC[N@@]4CC[C@@]3([H])C(C6=C(NC7=C8C=CC=C7)C8=CC=N6)=C5

Appearance: Solid powder

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

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 548.77 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Pathak RB, Dobson BC, Ghosh N, Ageel KA, Alshawish MR, Saruengkhanphasit R, Coldham I. Synthesis of the tricyclic core of manzamine A. Org Biomol Chem. 2015 Mar 21;13(11):3331-40. doi: 10.1039/c4ob02582b. PubMed PMID: 25647730.

2: Kallifatidis G, Hoepfner D, Jaeg T, Guzmán EA, Wright AE. 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. doi: 10.3390/md11093500. Erratum in: Mar Drugs. 2014;12(4):2305-7. PubMed PMID: 24048269; PubMed Central PMCID: PMC3806460.

3: Furusato A, Kato H, Nehira T, Eguchi K, Kawabata T, Fujiwara Y, Losung F, Mangindaan RE, de Voogd NJ, Takeya M, Yokosawa H, Tsukamoto S. Acanthomanzamines A-E with new manzamine frameworks from the marine sponge Acanthostrongylophora ingens. Org Lett. 2014 Aug 1;16(15):3888-91. doi: 10.1021/ol5015569. Epub 2014 Jun 26. PubMed PMID: 24967948.

4: Eguchi K, Fujiwara Y, Hayashida A, Horlad H, Kato H, Rotinsulu H, Losung F, Mangindaan RE, de Voogd NJ, Takeya M, Tsukamoto S. 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. doi: 10.1016/j.bmc.2013.04.025. Epub 2013 Apr 21. PubMed PMID: 23665143.

5: Kubota T, Kamijyo Y, Takahashi-Nakaguchi A, Fromont J, Gonoi T, Kobayashi J. Zamamiphidin A, a new manzamine related alkaloid from an Okinawan marine sponge Amphimedon sp. Org Lett. 2013 Feb 1;15(3):610-2. doi: 10.1021/ol3034274. Epub 2013 Jan 23. PubMed PMID: 23343122.

6: Jakubec P, Hawkins A, Felzmann W, Dixon DJ. Total synthesis of manzamine A and related alkaloids. J Am Chem Soc. 2012 Oct 24;134(42):17482-5. doi: 10.1021/ja308826x. Epub 2012 Oct 16. PubMed PMID: 23039372.

7: Palem JR, Bedadala GR, El Sayed KA, Hsia SC. 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. doi: 10.1055/s-0030-1250093. Epub 2010 Jul 19. PubMed PMID: 20645244.

8: Radwan M, Hanora A, Khalifa S, Abou-El-Ela SH. Manzamines: a potential for novel cures. Cell Cycle. 2012 May 1;11(9):1765-72. doi: 10.4161/cc.20135. Epub 2012 May 1. Review. PubMed PMID: 22510565.

9: Shulga DA, Osolodkin DI, Palyulin VA, Zefirov NS. Simulation of intramolecular hydrogen bond dynamics in manzamine A as a sensitive test for charge distribution quality. Nat Prod Commun. 2012 Mar;7(3):295-9. PubMed PMID: 22545399.

10: Guzmán EA, Johnson JD, Linley PA, Gunasekera SE, Wright AE. 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. PubMed PMID: 20352293; PubMed Central PMCID: PMC3085053.

11: Waters AL, Peraud O, Kasanah N, Sims JW, Kothalawala N, Anderson MA, Abbas SH, Rao KV, Jupally VR, Kelly M, Dass A, Hill RT, Hamann MT. An analysis of the sponge Acanthostrongylophora igens' microbiome yields an actinomycete that produces the natural product manzamine A. Front Mar Sci. 2014 Oct;1. pii: 54. Epub 2014 Oct 17. PubMed PMID: 27785452; PubMed Central PMCID: PMC5076551.

12: El-Desoky AH, Kato H, Eguchi K, Kawabata T, Fujiwara Y, Losung F, Mangindaan RE, de Voogd NJ, Takeya M, Yokosawa H, Tsukamoto S. Acantholactam and pre-neo-kauluamine, manzamine-related alkaloids from the Indonesian marine sponge Acanthostrongylophora ingens. J Nat Prod. 2014 Jun 27;77(6):1536-40. doi: 10.1021/np500290a. Epub 2014 Jun 5. PubMed PMID: 24902064.

13: Zhang B, Higuchi R, Miyamoto T, Van Soest RW. Neuritogenic activity-guided isolation of a free base form manzamine A from a marine sponge, Acanthostrongylophora aff. ingens (Thiele, 1899). Chem Pharm Bull (Tokyo). 2008 Jun;56(6):866-9. PubMed PMID: 18520099.

14: Samoylenko V, Khan SI, Jacoba MR, Tekwani BL, Walker LA, Hufford CD, Muhammad I. Bioactive (+)-manzamine A and (+)-8-hydroxymanzamine A tertiary bases and salts from Acanthostrongylophora ingens and their preparations. Nat Prod Commun. 2009 Feb;4(2):185-92. PubMed PMID: 19370920; PubMed Central PMCID: PMC3709442.

15: Herdemann M, Al-Mourabit A, Martin MT, Marazano C. From a biogenetic scenario to a synthesis of the ABC ring of manzamine A. J Org Chem. 2002 Mar 22;67(6):1890-7. PubMed PMID: 11895407.

16: 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. PubMed PMID: 16737321; PubMed Central PMCID: PMC4918909.

17: Ibrahim MA, Shilabin AG, Prasanna S, Jacob M, Khan SI, Doerksen RJ, Hamann MT. 2-N-Methyl modifications and SAR studies of manzamine A. Bioorg Med Chem. 2008 Jul 15;16(14):6702-6. doi: 10.1016/j.bmc.2008.05.079. Epub 2008 Jun 5. PubMed PMID: 18595720; PubMed Central PMCID: PMC2547340.

18: Toma T, Kita Y, Fukuyama T. Total synthesis of (+)-manzamine A. J Am Chem Soc. 2010 Aug 4;132(30):10233-5. doi: 10.1021/ja103721s. PubMed PMID: 20662499.

19: Sayed KA, Khalil AA, Yousaf M, Labadie G, Kumar GM, Franzblau SG, Mayer AM, Avery MA, Hamann MT. Semisynthetic studies on the manzamine alkaloids. J Nat Prod. 2008 Mar;71(3):300-8. doi: 10.1021/np0703702. Epub 2008 Jan 17. PubMed PMID: 18198837; PubMed Central PMCID: PMC4895205.

20: Rao KV, Donia MS, Peng J, Garcia-Palomero E, Alonso D, Martinez A, Medina M, Franzblau SG, Tekwani BL, Khan SI, Wahyuono S, Willett KL, Hamann MT. Manzamine B and E and ircinal A related alkaloids from an Indonesian Acanthostrongylophora sponge and their activity against infectious, tropical parasitic, and Alzheimer's diseases. J Nat Prod. 2006 Jul;69(7):1034-40. PubMed PMID: 16872140; PubMed Central PMCID: PMC4917200.