Lamellarin E

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 598245

CAS#: 115982-19-9

Description: Lamellarin E is an antineoplastic.


Chemical Structure

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Lamellarin E
CAS# 115982-19-9

Theoretical Analysis

MedKoo Cat#: 598245
Name: Lamellarin E
CAS#: 115982-19-9
Chemical Formula: C29H25NO9
Exact Mass: 531.1529
Molecular Weight: 531.51
Elemental Analysis: C, 65.53; H, 4.74; N, 2.64; O, 27.09

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.

Request quote for custom synthesis

Synonym: Lamellarin E;

IUPAC/Chemical Name: 3,10-dihydroxy-14-(3-hydroxy-4-methoxyphenyl)-2,11,12-trimethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one

InChi Key: JAYUXAMNSNMXCO-UHFFFAOYSA-N

InChi Code: InChI=1S/C29H25NO9/c1-35-19-6-5-13(9-17(19)31)23-24-16-11-21(36-2)18(32)12-20(16)39-29(34)26(24)30-8-7-14-15(25(23)30)10-22(37-3)28(38-4)27(14)33/h5-6,9-12,31-33H,7-8H2,1-4H3

SMILES Code: O=C1OC2=CC(O)=C(OC)C=C2C3=C1N(CCC4=C5C=C(OC)C(OC)=C4O)C5=C3C6=CC=C(OC)C(O)=C6

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: >3 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: 2934.99.03.00

Preparing Stock Solutions

The following data is based on the product molecular weight 531.51 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

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1: 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.

2: Tangdenpaisal K, Worayuthakarn R, Karnkla S, Ploypradith P, Intachote P, Sengsai S, Saimanee B, Ruchirawat S, Chittchang M. Designing new analogs for streamlining the structure of cytotoxic lamellarin natural products. Chem Asian J. 2015 Apr;10(4):925-37. doi: 10.1002/asia.201403361. Epub 2015 Feb 20. PubMed PMID: 25702829.

3: 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.

4: 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.

5: Huang XC, Xiao X, Zhang YK, Talele TT, Salim AA, Chen ZS, Capon RJ. Lamellarin O, a pyrrole alkaloid from an Australian marine sponge, Ianthella sp., reverses BCRP mediated drug resistance in cancer cells. Mar Drugs. 2014 Jun 27;12(7):3818-37. doi: 10.3390/md12073818. PubMed PMID: 24979269; PubMed Central PMCID: PMC4113800.

6: Gupton JT, Telang N, Patteson J, Lescalleet K, Yeudall S, Sobieski J, Harrison A, Curry W. The application of formyl group activation of bromopyrrole esters to formal syntheses of lycogarubin C, permethyl storniamide A and lamellarin G trimethyl ether. Tetrahedron. 2014 Dec 30;70(52):9759-9767. PubMed PMID: 25584014; PubMed Central PMCID: PMC4288030.

7: 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.

8: 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.

9: 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.

10: Kamiyama H, Kubo Y, Sato H, Yamamoto N, Fukuda T, Ishibashi F, Iwao M. Synthesis, structure-activity relationships, and mechanism of action of anti-HIV-1 lamellarin α 20-sulfate analogues. Bioorg Med Chem. 2011 Dec 15;19(24):7541-50. doi: 10.1016/j.bmc.2011.10.030. Epub 2011 Oct 20. PubMed PMID: 22071527.

11: Imbri D, Tauber J, Opatz T. A high-yielding modular access to the lamellarins: synthesis of lamellarin G trimethyl ether, lamellarin η and dihydrolamellarin η. Chemistry. 2013 Nov 4;19(45):15080-3. doi: 10.1002/chem.201303563. Epub 2013 Oct 7. PubMed PMID: 24123481.

12: Kluza J, Gallego MA, Loyens A, Beauvillain JC, Sousa-Faro JM, Cuevas C, Marchetti P, Bailly C. Cancer cell mitochondria are direct proapoptotic targets for the marine antitumor drug lamellarin D. Cancer Res. 2006 Mar 15;66(6):3177-87. PubMed PMID: 16540669.

13: Ridley CP, Reddy MV, Rocha G, Bushman FD, Faulkner DJ. Total synthesis and evaluation of lamellarin alpha 20-Sulfate analogues. Bioorg Med Chem. 2002 Oct;10(10):3285-90. PubMed PMID: 12150874.

14: Reddy MV, Rao MR, Rhodes D, Hansen MS, Rubins K, Bushman FD, Venkateswarlu Y, Faulkner DJ. Lamellarin alpha 20-sulfate, an inhibitor of HIV-1 integrase active against HIV-1 virus in cell culture. J Med Chem. 1999 Jun 3;42(11):1901-7. PubMed PMID: 10354398.

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: 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.

17: Krishnaiah P, Reddy VL, Venkataramana G, Ravinder K, Srinivasulu M, Raju TV, Ravikumar K, Chandrasekar D, Ramakrishna S, Venkateswarlu Y. New lamellarin alkaloids from the Indian ascidian Didemnum obscurum and their antioxidant properties. J Nat Prod. 2004 Jul;67(7):1168-71. PubMed PMID: 15270574.

18: Pungkham H, Swatdipakdi N, Theerasilp M, Karnkla S, Chittchang M, Ploypradith P, Nasongkla N. PEG-b-PCL and PEG-b-PLA polymeric micelles as nanocarrieres for lamellarin N delivery. Conf Proc IEEE Eng Med Biol Soc. 2011;2011:3245-8. doi: 10.1109/IEMBS.2011.6090882. PubMed PMID: 22255031.

19: 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.

20: Davis RA, Carroll AR, Pierens GK, Quinn RJ. New lamellarin alkaloids from the australian ascidian, didemnum chartaceum . J Nat Prod. 1999 Mar;62(3):419-24. PubMed PMID: 10096849.