Page last updated: 2024-11-11

lamellarin d

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Description

lamellarin D: a benzo-isoquinoline-coumarin [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID9892144
CHEMBL ID373114
SCHEMBL ID14106879
MeSH IDM0425729

Synonyms (17)

Synonym
CHEMBL373114
lamellarin d
lamellarin-d
97614-65-8
lamellarine d
unii-yef6xd93ve
yef6xd93ve ,
SCHEMBL14106879
3,11-dihydroxy-14-(4-hydroxy-3-methoxyphenyl)-2,12-dimethoxy-6h-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one
Q18344928
7,17-dihydroxy-12-(4-hydroxy-3-methoxyphenyl)-8,16-dimethoxy-4-oxa-1-azapentacyclo[11.8.0.02,11.05,10.014,19]henicosa-2(11),5,7,9,12,14,16,18,20-nonaen-3-one
7,17-dihydroxy-12-(4-hydroxy-3-methoxyphenyl)-8,16-dimethoxy-4-oxa-1-azapentacyclo[11.8.0.0{2,11}.0{5,10}.0{14,19}]henicosa-2(11),5(10),6,8,12,14,16,18,20-nonaen-3-one
6h-(1)benzopyrano(4',3':4,5)pyrrolo(2,1-a)isoquinolin-6-one, 3,11-dihydroxy-14-(4-hydroxy-3-methoxyphenyl)-2,12-dimethoxy-, (+/-)-
3,11-dihydroxy-14-(4-hydroxy-3-methoxyphenyl)-2,12-dimethoxy-6h-(1)benzopyrano(4',3':4,5)pyrrolo(2,1-a)isoquinolin-6-one
6h-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one, 3,11-dihydroxy-14-(4-hydroxy-3-methoxyphenyl)-2,12-dimethoxy-
DTXSID501031665
AKOS040752394

Research Excerpts

Overview

Lamellarin D (LamD) is a hexacyclic pyrole alkaloid isolated from marine invertebrates. Its biologic properties have been attributed to mitochondrial targeting. It is a marine alkaloids with a pronounced cytotoxicity against a large panel of cancer cell lines.

ExcerptReferenceRelevance
"Lamellarin D (LamD) is a marine alkaloid with broad spectrum antitumor activities. "( Another facet to the anticancer response to lamellarin D: induction of cellular senescence through inhibition of topoisomerase I and intracellular Ros production.
Ballot, C; Buche, S; Formstecher, P; Jendoubi, M; Kluza, J; Marchetti, P; Martoriati, A; Mortier, L, 2014
)
2.11
"Lamellarin D (Lam-D) is a hexacyclic pyrole alkaloid isolated from marine invertebrates, whose biologic properties have been attributed to mitochondrial targeting. "( Poisoning of mitochondrial topoisomerase I by lamellarin D.
Agama, K; Agrawal, S; Dalla Rosa, I; Fesen, K; Khiati, S; Neuman, KC; Pommier, Y; Seol, Y; Zhang, H, 2014
)
2.1
"Lamellarin D (LamD) is a marine alkaloid with a pronounced cytotoxicity against a large panel of cancer cells, affecting cell growth and inducing apoptosis. "( Inhibition effects of lamellarin D on human leukemia K562 cell proliferation and underlying mechanisms.
Lin, H; Wang, D; Wang, J; Zhang, N; Zhu, Y, 2014
)
2.16
"Lamellarin D (LAM-D) is a marine alkaloid endowed with potent cytotoxic activities against various tumor cells, in particular human prostate cancer cells and leukemia cells. "( Lamellarin D: a novel pro-apoptotic agent from marine origin insensitive to P-glycoprotein-mediated drug efflux.
Bailly, C; Cuevas, C; Kluza, J; Lansiaux, A; Otero, G; Tardy, C; Vanhuyse, M, 2005
)
3.21
"Lamellarin D is a marine alkaloid with a pronounced cytotoxicity against a large panel of cancer cell lines and is a potent inhibitor of topoisomerase I. "( Cancer cell mitochondria are direct proapoptotic targets for the marine antitumor drug lamellarin D.
Bailly, C; Beauvillain, JC; Cuevas, C; Gallego, MA; Kluza, J; Loyens, A; Marchetti, P; Sousa-Faro, JM, 2006
)
2
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (44)

Assay IDTitleYearJournalArticle
AID1515359Antiproliferative activity against human ACHN cells after 48 hrs by SRB assay2019Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2
Lamellarin-inspired potent topoisomerase I inhibitors with the unprecedented benzo[g][1]benzopyrano[4,3-b]indol-6(13H)-one scaffold.
AID1162581Antiproliferative activity against human MDA-MB-231 cells assessed as growth inhibition after 72 hrs by MTT assay2014European journal of medicinal chemistry, Oct-06, Volume: 85Design and total synthesis of Mannich derivatives of marine natural product lamellarin D as cytotoxic agents.
AID1515347Antiproliferative activity against human NCI-H522 cells after 48 hrs by SRB assay2019Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2
Lamellarin-inspired potent topoisomerase I inhibitors with the unprecedented benzo[g][1]benzopyrano[4,3-b]indol-6(13H)-one scaffold.
AID1162580Antiproliferative activity against human HT-29 cells assessed as growth inhibition after 72 hrs by MTT assay2014European journal of medicinal chemistry, Oct-06, Volume: 85Design and total synthesis of Mannich derivatives of marine natural product lamellarin D as cytotoxic agents.
AID1515334Antiproliferative activity against human U251 cells after 48 hrs by SRB assay2019Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2
Lamellarin-inspired potent topoisomerase I inhibitors with the unprecedented benzo[g][1]benzopyrano[4,3-b]indol-6(13H)-one scaffold.
AID1732036Cytotoxicity against human HGC-27 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay2021European journal of medicinal chemistry, Mar-15, Volume: 214Design, Synthesis and Structure-Activity Relationship Studies of Glycosylated Derivatives of Marine Natural Product Lamellarin D.
AID1162582Antiproliferative activity against human K562 cells assessed as growth inhibition after 72 hrs by MTT assay2014European journal of medicinal chemistry, Oct-06, Volume: 85Design and total synthesis of Mannich derivatives of marine natural product lamellarin D as cytotoxic agents.
AID1515366Antiproliferative activity against human DU145 cells after 48 hrs by SRB assay2019Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2
Lamellarin-inspired potent topoisomerase I inhibitors with the unprecedented benzo[g][1]benzopyrano[4,3-b]indol-6(13H)-one scaffold.
AID338960Cytotoxicity against human HeLa cells assessed as inhibition of colony formation after 5 to 8 days by colony assay2002Journal of natural products, Apr, Volume: 65, Issue:4
Synthesis and structure-activity relationship study of lamellarin derivatives.
AID1515352Antiproliferative activity against human LOXIMVI cells after 48 hrs by SRB assay2019Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2
Lamellarin-inspired potent topoisomerase I inhibitors with the unprecedented benzo[g][1]benzopyrano[4,3-b]indol-6(13H)-one scaffold.
AID338962Cytotoxicity against african green monkey Vero cells assessed as inhibition of colony formation after 5 to 8 days by colony assay2002Journal of natural products, Apr, Volume: 65, Issue:4
Synthesis and structure-activity relationship study of lamellarin derivatives.
AID644575Inhibition of human topoisomerase 1-mediated relaxation of supercoiled plasmid pUC19 DNA at 100 uM by agarose gel electrophoresis2012European journal of medicinal chemistry, Mar, Volume: 49Synthesis of chromeno[3,4-b]indoles as Lamellarin D analogues: a novel DYRK1A inhibitor class.
AID1732040Inhibition of topoisomerase 1 (unknown origin) assessed as reduction in relaxation of supercoiled plasmid pBR322 DNA at 10 uM incubated for 30 mins by agarose gel electrophoresis2021European journal of medicinal chemistry, Mar-15, Volume: 214Design, Synthesis and Structure-Activity Relationship Studies of Glycosylated Derivatives of Marine Natural Product Lamellarin D.
AID1732041Induction of cell cycle arrest in human MDA-MB-231 cells assessed as increase in accumulation of G2/M phase incubated for 24 hrs by PI staining based flow cytometry analysis2021European journal of medicinal chemistry, Mar-15, Volume: 214Design, Synthesis and Structure-Activity Relationship Studies of Glycosylated Derivatives of Marine Natural Product Lamellarin D.
AID265672Antiproliferative activity against human HT29 cell line after 72 hrs by SRB assay2006Journal of medicinal chemistry, Jun-01, Volume: 49, Issue:11
Synthesis and structure-activity relationship study of potent cytotoxic analogues of the marine alkaloid Lamellarin D.
AID644574Inhibition of human topoisomerase 1-mediated relaxation of supercoiled plasmid pUC19 DNA at 20 uM by agarose gel electrophoresis2012European journal of medicinal chemistry, Mar, Volume: 49Synthesis of chromeno[3,4-b]indoles as Lamellarin D analogues: a novel DYRK1A inhibitor class.
AID1732035Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay2021European journal of medicinal chemistry, Mar-15, Volume: 214Design, Synthesis and Structure-Activity Relationship Studies of Glycosylated Derivatives of Marine Natural Product Lamellarin D.
AID1732039Cytotoxicity against human HepG2 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay2021European journal of medicinal chemistry, Mar-15, Volume: 214Design, Synthesis and Structure-Activity Relationship Studies of Glycosylated Derivatives of Marine Natural Product Lamellarin D.
AID644576Cytotoxicity against human CEM cells2012European journal of medicinal chemistry, Mar, Volume: 49Synthesis of chromeno[3,4-b]indoles as Lamellarin D analogues: a novel DYRK1A inhibitor class.
AID338963Cytotoxicity against MDCK cells assessed as inhibition of colony formation after 5 to 8 days by colony assay2002Journal of natural products, Apr, Volume: 65, Issue:4
Synthesis and structure-activity relationship study of lamellarin derivatives.
AID1859462Cytotoxicity against human CEM cells assessed as cell growth inhibition2022European journal of medicinal chemistry, Jun-05, Volume: 236Topoisomerase I inhibitors: Challenges, progress and the road ahead.
AID1732037Cytotoxicity against human A549 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay2021European journal of medicinal chemistry, Mar-15, Volume: 214Design, Synthesis and Structure-Activity Relationship Studies of Glycosylated Derivatives of Marine Natural Product Lamellarin D.
AID248114Inhibitory concentration against CEM/C2 cell growth after incubation in liquid medium for 72 h2005Journal of medicinal chemistry, Jun-02, Volume: 48, Issue:11
Molecular determinants of topoisomerase I poisoning by lamellarins: comparison with camptothecin and structure-activity relationships.
AID612419Stimulation of human recombinant DNA topoisomerase 1-mediated 751-bp BamHI-EcoRV fragment of SV40 DNA cleavage at 1 to 50 uM after 30 mins by polyacrylamide gel-electrophoresis2011Bioorganic & medicinal chemistry, Aug-15, Volume: 19, Issue:16
Synthesis and topoisomerase I inhibitory activity of a novel diazaindeno[2,1-b]phenanthrene analogue of Lamellarin D.
AID1515357Antiproliferative activity against human SKOV3 cells after 48 hrs by SRB assay2019Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2
Lamellarin-inspired potent topoisomerase I inhibitors with the unprecedented benzo[g][1]benzopyrano[4,3-b]indol-6(13H)-one scaffold.
AID1515328Inhibition of calf thymus DNA topoisomerase 1 assessed as reduction in enzyme-mediated relaxation of supercoiled pBR322 plasmid DNA at 10 uM after 30 mins by ethidium bromide staining-based agarose gel electrophoresis2019Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2
Lamellarin-inspired potent topoisomerase I inhibitors with the unprecedented benzo[g][1]benzopyrano[4,3-b]indol-6(13H)-one scaffold.
AID612418Antiproliferative activity against human NCI-H460 cells after 72 hrs by coulter counter analysis2011Bioorganic & medicinal chemistry, Aug-15, Volume: 19, Issue:16
Synthesis and topoisomerase I inhibitory activity of a novel diazaindeno[2,1-b]phenanthrene analogue of Lamellarin D.
AID1515332Antiproliferative activity against human MCF7 cells after 48 hrs by SRB assay2019Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2
Lamellarin-inspired potent topoisomerase I inhibitors with the unprecedented benzo[g][1]benzopyrano[4,3-b]indol-6(13H)-one scaffold.
AID1859461Cytotoxicity against mouse P388 cells assessed as cell growth inhibition2022European journal of medicinal chemistry, Jun-05, Volume: 236Topoisomerase I inhibitors: Challenges, progress and the road ahead.
AID1515327Inhibition of calf thymus DNA topoisomerase 1 assessed as reduction in enzyme-mediated relaxation of supercoiled pBR322 plasmid DNA at 10 uM after 30 mins by agarose gel electrophoresis2019Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2
Lamellarin-inspired potent topoisomerase I inhibitors with the unprecedented benzo[g][1]benzopyrano[4,3-b]indol-6(13H)-one scaffold.
AID248046Inhibitory concentration against CEM cell growth after incubation in liquid medium for 72 h2005Journal of medicinal chemistry, Jun-02, Volume: 48, Issue:11
Molecular determinants of topoisomerase I poisoning by lamellarins: comparison with camptothecin and structure-activity relationships.
AID245764Ratio of IC50 against CPT-resistant cell line to that of CPT-sensitive cell line expressed as relative resistant index2005Journal of medicinal chemistry, Jun-02, Volume: 48, Issue:11
Molecular determinants of topoisomerase I poisoning by lamellarins: comparison with camptothecin and structure-activity relationships.
AID265674Antiproliferative activity against human MDA-MB-231 cell line after 72 hrs by SRB assay2006Journal of medicinal chemistry, Jun-01, Volume: 49, Issue:11
Synthesis and structure-activity relationship study of potent cytotoxic analogues of the marine alkaloid Lamellarin D.
AID338964Cytotoxicity against MDCK cells at 1 mM by MTT assay2002Journal of natural products, Apr, Volume: 65, Issue:4
Synthesis and structure-activity relationship study of lamellarin derivatives.
AID1515363Antiproliferative activity against human MKN28 cells after 48 hrs by SRB assay2019Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2
Lamellarin-inspired potent topoisomerase I inhibitors with the unprecedented benzo[g][1]benzopyrano[4,3-b]indol-6(13H)-one scaffold.
AID1732043Aqueous solubility of compound in deionized water by HPLC-HRMS analysis2021European journal of medicinal chemistry, Mar-15, Volume: 214Design, Synthesis and Structure-Activity Relationship Studies of Glycosylated Derivatives of Marine Natural Product Lamellarin D.
AID771148Inhibition of calf thymus DNA topoisomerase 1-mediated relaxation of supercoiled pBR322 plasmid DNA at 50 uM 30 mins by ethidium bromide staining2013Journal of medicinal chemistry, Sep-26, Volume: 56, Issue:18
Synthesis, resolution, and biological evaluation of atropisomeric (aR)- and (aS)-16-methyllamellarins N: unique effects of the axial chirality on the selectivity of protein kinases inhibition.
AID265670Antiproliferative activity against human A549 cell line after 72 hrs by SRB assay2006Journal of medicinal chemistry, Jun-01, Volume: 49, Issue:11
Synthesis and structure-activity relationship study of potent cytotoxic analogues of the marine alkaloid Lamellarin D.
AID612417Antiproliferative activity against human NCI-H460 cells after 1 hr by coulter counter analysis2011Bioorganic & medicinal chemistry, Aug-15, Volume: 19, Issue:16
Synthesis and topoisomerase I inhibitory activity of a novel diazaindeno[2,1-b]phenanthrene analogue of Lamellarin D.
AID1162583Antiproliferative activity against human HepG2 cells assessed as growth inhibition after 72 hrs by MTT assay2014European journal of medicinal chemistry, Oct-06, Volume: 85Design and total synthesis of Mannich derivatives of marine natural product lamellarin D as cytotoxic agents.
AID1515344Antiproliferative activity against human HCT116 cells after 48 hrs by SRB assay2019Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2
Lamellarin-inspired potent topoisomerase I inhibitors with the unprecedented benzo[g][1]benzopyrano[4,3-b]indol-6(13H)-one scaffold.
AID338961Cytotoxicity against rat XC cells assessed as inhibition of colony formation after 5 to 8 days by colony assay2002Journal of natural products, Apr, Volume: 65, Issue:4
Synthesis and structure-activity relationship study of lamellarin derivatives.
AID1162584Inhibition of calf thymus Topoisomerase 1-mediated relaxation of supercoiled pBR322 DNA at 100 uM after 30 mins by gel electrophoresis2014European journal of medicinal chemistry, Oct-06, Volume: 85Design and total synthesis of Mannich derivatives of marine natural product lamellarin D as cytotoxic agents.
AID1732038Cytotoxicity against human HCT-116 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay2021European journal of medicinal chemistry, Mar-15, Volume: 214Design, Synthesis and Structure-Activity Relationship Studies of Glycosylated Derivatives of Marine Natural Product Lamellarin D.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (40)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's16 (40.00)29.6817
2010's22 (55.00)24.3611
2020's2 (5.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.85

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index10.85 (24.57)
Research Supply Index3.71 (2.92)
Research Growth Index4.57 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.85)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (7.50%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other37 (92.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]