Lamellarin D

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MedKoo CAT#: 525211

CAS#: 97614-65-8

Description: Lamellarin D is a natural product related to Lamellarins, which are a group of pyrrole alkaloids first isolated in 1985 from the marine mollusk Lamellaria in the waters of Palau. Over 70 lamellarins and similar compounds were subsequently isolated. Other similar compounds include ningalins, lukianols, polycitones, and storniamides. These compounds have shown a wide variety of biological activity, including reversal of multidrug resistance, HIV-1 integrase inhibition, and antibiotic activity. Lamellarin D, for example, displays strong cytotoxic activity against tumor cell lines, and is a potent topoisomerase I inhibitor.

Chemical Structure

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Lamellarin D
CAS# 97614-65-8
Instruction

Theoretical Analysis

MedKoo Cat#: 525211
Name: Lamellarin D
CAS#: 97614-65-8
Chemical Formula: C28H21NO8
Exact Mass: 499.13
Molecular Weight: 499.475
Elemental Analysis: C, 67.33; H, 4.24; N, 2.80; O, 25.63

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Lamellarin D

IUPAC/Chemical Name: 3,11-Dihydroxy-14-(4-hydroxy-3-methoxyphenyl)-2,12-dimethoxy-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one

InChi Key: ATHLLZUXVPNPAW-UHFFFAOYSA-N

InChi Code: InChI=1S/C28H21NO8/c1-34-21-9-14(4-5-17(21)30)24-25-16-11-23(36-3)19(32)12-20(16)37-28(33)27(25)29-7-6-13-8-18(31)22(35-2)10-15(13)26(24)29/h4-12,30-32H,1-3H3

SMILES Code: O=C1OC2=C(C3=C1N(C=CC4=C5C=C(OC)C(O)=C4)C5=C3C6=CC=C(O)C(OC)=C6)C=C(OC)C(O)=C2

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 499.48 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: Lade DM, Pawar AB, Mainkar PS, Chandrasekhar S. Total Synthesis of Lamellarin D Trimethyl Ether, Lamellarin D, and Lamellarin H. J Org Chem. 2017 May 5;82(9):4998-5004. doi: 10.1021/acs.joc.7b00636. Epub 2017 Apr 24. PubMed PMID: 28421766.

2: Colligs V, Hansen SP, Imbri D, Seo EJ, Kadioglu O, Efferth T, Opatz T. Synthesis and biological evaluation of a D-ring-contracted analogue of lamellarin D. Bioorg Med Chem. 2017 Feb 9. pii: S0968-0896(16)31109-9. doi: 10.1016/j.bmc.2017.02.005. [Epub ahead of print] PubMed PMID: 28233677.

3: Dahmane N, Gadelle D, Delmas S, Criscuolo A, Eberhard S, Desnoues N, Collin S, Zhang H, Pommier Y, Forterre P, Sezonov G. topIb, a phylogenetic hallmark gene of Thaumarchaeota encodes a functional eukaryote-like topoisomerase IB. Nucleic Acids Res. 2016 Apr 7;44(6):2795-805. doi: 10.1093/nar/gkw097. Epub 2016 Feb 22. PubMed PMID: 26908651; PubMed Central PMCID: PMC4824112.

4: Manjappa KB, Syu JR, Yang DY. Visible-Light-Promoted and Yb(OTf)3-Catalyzed Constructions of Coumarin-Pyrrole-(Iso)quinoline-Fused Pentacycles: Synthesis of Lamellarin Core, Lamellarin D Trimethyl Ether, and Lamellarin H. Org Lett. 2016 Jan 15;18(2):332-5. doi: 10.1021/acs.orglett.5b03524. Epub 2016 Jan 7. PubMed PMID: 26741300.

5: Dialer C, Imbri D, Hansen SP, Opatz T. Synthesis of Lamellarin D Trimethyl Ether and Lamellarin H via 6π-Electrocyclization. J Org Chem. 2015 Nov 20;80(22):11605-10. doi: 10.1021/acs.joc.5b02194. Epub 2015 Oct 29. PubMed PMID: 26473557.

6: Seol Y, Zhang H, Agama K, Lorence N, Pommier Y, Neuman KC. Single-Molecule Supercoil Relaxation Assay as a Screening Tool to Determine the Mechanism and Efficacy of Human Topoisomerase IB Inhibitors. Mol Cancer Ther. 2015 Nov;14(11):2552-9. doi: 10.1158/1535-7163.MCT-15-0454. Epub 2015 Sep 8. PubMed PMID: 26351326; PubMed Central PMCID: PMC4636450.

7: Bailly C. Anticancer properties of lamellarins. Mar Drugs. 2015 Feb 19;13(3):1105-23. doi: 10.3390/md13031105. Review. PubMed PMID: 25706633; PubMed Central PMCID: PMC4377975.

8: Zhang N, Wang D, Zhu Y, Wang J, Lin H. Inhibition effects of lamellarin D on human leukemia K562 cell proliferation and underlying mechanisms. Asian Pac J Cancer Prev. 2014;15(22):9915-9. PubMed PMID: 25520128.

9: Shen L, Xie N, Yang B, Hu Y, Zhang Y. Design and total synthesis of Mannich derivatives of marine natural product lamellarin D as cytotoxic agents. Eur J Med Chem. 2014 Oct 6;85:807-17. doi: 10.1016/j.ejmech.2014.08.038. Epub 2014 Aug 12. PubMed PMID: 25189362.

10: Khiati S, Seol Y, Agama K, Dalla Rosa I, Agrawal S, Fesen K, Zhang H, Neuman KC, Pommier Y. Poisoning of mitochondrial topoisomerase I by lamellarin D. Mol Pharmacol. 2014 Aug;86(2):193-9. doi: 10.1124/mol.114.092833. Epub 2014 Jun 2. PubMed PMID: 24890608; PubMed Central PMCID: PMC4127927.

11: Jakubík J, Zimčík P, Randáková A, Fuksová K, El-Fakahany EE, Doležal V. Molecular mechanisms of methoctramine binding and selectivity at muscarinic acetylcholine receptors. Mol Pharmacol. 2014 Aug;86(2):180-92. doi: 10.1124/mol.114.093310. Epub 2014 May 28. PubMed PMID: 24870405.

12: Ballot C, Martoriati A, Jendoubi M, Buche S, Formstecher P, Mortier L, Kluza J, Marchetti P. Another facet to the anticancer response to lamellarin D: induction of cellular senescence through inhibition of topoisomerase I and intracellular Ros production. Mar Drugs. 2014 Jan 27;12(2):779-98. doi: 10.3390/md12020779. PubMed PMID: 24473175; PubMed Central PMCID: PMC3944515.

13: Menna M. Important classes of bioactive alkaloids from marine ascidians: structures, isolation and bioactivity. Curr Top Med Chem. 2014;14(2):207-23. Review. PubMed PMID: 24359200.

14: Neagoie C, Vedrenne E, Buron F, Mérour JY, Rosca S, Bourg S, Lozach O, Meijer L, Baldeyrou B, Lansiaux A, Routier S. Synthesis of chromeno[3,4-b]indoles as Lamellarin D analogues: a novel DYRK1A inhibitor class. Eur J Med Chem. 2012 Mar;49:379-96. doi: 10.1016/j.ejmech.2012.01.040. Epub 2012 Jan 25. PubMed PMID: 22305342.

15: Cananzi S, Merlini L, Artali R, Beretta GL, Zaffaroni N, Dallavalle S. Synthesis and topoisomerase I inhibitory activity of a novel diazaindeno[2,1-b]phenanthrene analogue of Lamellarin D. Bioorg Med Chem. 2011 Aug 15;19(16):4971-84. doi: 10.1016/j.bmc.2011.06.056. Epub 2011 Jul 2. PubMed PMID: 21783369.

16: Li Q, Jiang J, Fan A, Cui Y, Jia Y. Total synthesis of lamellarins D, H, and R and ningalin B. Org Lett. 2011 Jan 21;13(2):312-5. doi: 10.1021/ol1027877. Epub 2010 Dec 17. PubMed PMID: 21175172.

17: Bayet-Robert M, Lim S, Barthomeuf C, Morvan D. Biochemical disorders induced by cytotoxic marine natural products in breast cancer cells as revealed by proton NMR spectroscopy-based metabolomics. Biochem Pharmacol. 2010 Oct 15;80(8):1170-9. doi: 10.1016/j.bcp.2010.07.007. Epub 2010 Jul 15. PubMed PMID: 20637732.

18: Ballot C, Kluza J, Lancel S, Martoriati A, Hassoun SM, Mortier L, Vienne JC, Briand G, Formstecher P, Bailly C, Nevière R, Marchetti P. Inhibition of mitochondrial respiration mediates apoptosis induced by the anti-tumoral alkaloid lamellarin D. Apoptosis. 2010 Jul;15(7):769-81. doi: 10.1007/s10495-010-0471-2. PubMed PMID: 20151196.

19: Ballot C, Kluza J, Martoriati A, Nyman U, Formstecher P, Joseph B, Bailly C, Marchetti P. Essential role of mitochondria in apoptosis of cancer cells induced by the marine alkaloid Lamellarin D. Mol Cancer Ther. 2009 Dec;8(12):3307-17. doi: 10.1158/1535-7163.MCT-09-0639. PubMed PMID: 19952118.

20: Shen L, Yang X, Yang B, He Q, Hu Y. Novel hybrids from lamellarin D and combretastatin A 4 as cytotoxic agents. Eur J Med Chem. 2010 Jan;45(1):11-8. doi: 10.1016/j.ejmech.2009.09.017. Epub 2009 Sep 16. PubMed PMID: 19815316.