Compounds > arc111
Page last updated: 2024-11-11

arc111

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Description

topovale: topoisomerase I-targeting anticancer drug; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID9888428
CHEMBL ID70790
SCHEMBL ID241242
MeSH IDM0461456

Synonyms (19)

Synonym
8,9-dimethoxy-2,3-methylenedioxy-5-[2-(n,n-dimethylamino)ethyl]-5h-dibenzo[c,h]1,6-naphthyridin-6-one
CHEMBL70790
arc-111
topovale
SCHEMBL241242
benzo(c)(1,3)benzodioxolo(5,6-h)(1,6)naphthyridin-13(12h)-one, 12-(2-(dimethylamino)ethyl)-2,3-dimethoxy-
unii-7gl8k930u6
500214-53-9
topoval
7gl8k930u6 ,
8,9-dimethoxy-2,3-methylenedioxy-5-[2-(n,n- dimethylamino)ethyl]-5h-dibenzo[c,h]1,6-naphthyridin-6-one
UVXCXZBZPFCAAJ-UHFFFAOYSA-N
12-(2-(dimethylamino)ethyl)-2,3-dimethoxy-[1,3]dioxolo[4',5':4,5]benzo[1,2-h]benzo[c][1,6]naphthyridin-13(12h)-one ,
21-[2-(dimethylamino)ethyl]-16,17-dimethoxy-5,7-dioxa-11,21-diazapentacyclo[11.8.0.02,10.04,8.014,19]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-one
Q27268255
arc-111topoval
arc 111
arc111
AKOS040759660
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
DNA topoisomerase 1Homo sapiens (human)IC10 (µMol)0.00030.00020.00030.0003AID362301
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (11)

Processvia Protein(s)Taxonomy
DNA topological changeDNA topoisomerase 1Homo sapiens (human)
chromatin remodelingDNA topoisomerase 1Homo sapiens (human)
circadian rhythmDNA topoisomerase 1Homo sapiens (human)
response to xenobiotic stimulusDNA topoisomerase 1Homo sapiens (human)
programmed cell deathDNA topoisomerase 1Homo sapiens (human)
phosphorylationDNA topoisomerase 1Homo sapiens (human)
peptidyl-serine phosphorylationDNA topoisomerase 1Homo sapiens (human)
circadian regulation of gene expressionDNA topoisomerase 1Homo sapiens (human)
embryonic cleavageDNA topoisomerase 1Homo sapiens (human)
chromosome segregationDNA topoisomerase 1Homo sapiens (human)
DNA replicationDNA topoisomerase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (13)

Processvia Protein(s)Taxonomy
RNA polymerase II cis-regulatory region sequence-specific DNA bindingDNA topoisomerase 1Homo sapiens (human)
DNA bindingDNA topoisomerase 1Homo sapiens (human)
chromatin bindingDNA topoisomerase 1Homo sapiens (human)
double-stranded DNA bindingDNA topoisomerase 1Homo sapiens (human)
single-stranded DNA bindingDNA topoisomerase 1Homo sapiens (human)
RNA bindingDNA topoisomerase 1Homo sapiens (human)
DNA topoisomerase type I (single strand cut, ATP-independent) activityDNA topoisomerase 1Homo sapiens (human)
protein serine/threonine kinase activityDNA topoisomerase 1Homo sapiens (human)
protein bindingDNA topoisomerase 1Homo sapiens (human)
ATP bindingDNA topoisomerase 1Homo sapiens (human)
DNA binding, bendingDNA topoisomerase 1Homo sapiens (human)
protein domain specific bindingDNA topoisomerase 1Homo sapiens (human)
supercoiled DNA bindingDNA topoisomerase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
nuclear chromosomeDNA topoisomerase 1Homo sapiens (human)
P-bodyDNA topoisomerase 1Homo sapiens (human)
fibrillar centerDNA topoisomerase 1Homo sapiens (human)
male germ cell nucleusDNA topoisomerase 1Homo sapiens (human)
nucleusDNA topoisomerase 1Homo sapiens (human)
nucleoplasmDNA topoisomerase 1Homo sapiens (human)
nucleolusDNA topoisomerase 1Homo sapiens (human)
perikaryonDNA topoisomerase 1Homo sapiens (human)
protein-DNA complexDNA topoisomerase 1Homo sapiens (human)
nucleolusDNA topoisomerase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (87)

Assay IDTitleYearJournalArticle
AID362303Cytotoxicity against human camptothecin-resistant CPT-K5 cells after 4 days by MTT assay2008Bioorganic & medicinal chemistry, Aug-15, Volume: 16, Issue:16
Syntheses and biological evaluation of topoisomerase I-targeting agents related to 11-[2-(N,N-dimethylamino)ethyl]-2,3-dimethoxy-8,9-methylenedioxy-11H-isoquino[4,3-c]cinnolin-12-one (ARC-31).
AID414754Cytotoxicity against human RPMI8402 cells after 4 days by MTT method2009Bioorganic & medicinal chemistry, Apr-01, Volume: 17, Issue:7
12-Substituted 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridines as novel topoisomerase I-targeting antitumor agents.
AID409906Cytotoxicity against human KB3-1 cells by MTT method2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
11-Substituted 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine derivatives as novel topoisomerase I-targeting agents.
AID1708527Growth inhibition of human HCT-116 cells by Cell-titer96 assay2021Journal of medicinal chemistry, 02-11, Volume: 64, Issue:3
Copper(I)-Catalyzed Nitrile-Addition/
AID1708541Resistance index, ratio of GI50 for growth inhibition of ARC-111-resistant human HA6n cells to GI50 for growth inhibition of human HCT-116 cells2021Journal of medicinal chemistry, 02-11, Volume: 64, Issue:3
Copper(I)-Catalyzed Nitrile-Addition/
AID110875In vivo antitumor activity in NCR-nude-nude mice inoculated with 1.2 E6 -1.5 E6 MDA-MB-435 cells after day 7 with an average dose of 0.73 mg/mouse (ip)2002Bioorganic & medicinal chemistry letters, Nov-18, Volume: 12, Issue:22
Diaza- and triazachrysenes: potent topoisomerase-targeting agents with exceptional antitumor activity against the human tumor xenograft, MDA-MB-435.
AID433914Effect on human topoisomerase 1 expressed in Sf9 insect cells assessed as effective concentration required for 10% cleavage of plasmid DNA relative to topotecan2009European journal of medicinal chemistry, Sep, Volume: 44, Issue:9
Novel topoisomerase I-targeting antitumor agents synthesized from the N,N,N-trimethylammonium derivative of ARC-111, 5H-2,3-dimethoxy-8,9-methylenedioxy-5-[(2-N,N,N-trimethylammonium)ethyl]dibenzo[c,h][1,6]naphthyridin-6-one iodide.
AID247768Inhibitory concentration against KB/V-1 cells overexpress MDR12005Journal of medicinal chemistry, Feb-10, Volume: 48, Issue:3
5-(2-aminoethyl)dibenzo[c,h][1,6]naphthyridin-6-ones: variation of n-alkyl substituents modulates sensitivity to efflux transporters associated with multidrug resistance.
AID434074Cytotoxicity against multidrug resistant human KBH5.0 cells overexpressing BCRP after 4 days by MTT assay2009European journal of medicinal chemistry, Sep, Volume: 44, Issue:9
Novel topoisomerase I-targeting antitumor agents synthesized from the N,N,N-trimethylammonium derivative of ARC-111, 5H-2,3-dimethoxy-8,9-methylenedioxy-5-[(2-N,N,N-trimethylammonium)ethyl]dibenzo[c,h][1,6]naphthyridin-6-one iodide.
AID251002Relative topoisomerase I-mediated plasmid DNA cleavage compared to topotecan2005Journal of medicinal chemistry, Feb-10, Volume: 48, Issue:3
5-(2-aminoethyl)dibenzo[c,h][1,6]naphthyridin-6-ones: variation of n-alkyl substituents modulates sensitivity to efflux transporters associated with multidrug resistance.
AID56880Effective concentration required to cleave DNA, mediated by human DNA topoisomerase I (TOP1) reported as REC i.e. concentration relative to topotecan (assumed as 1)2003Journal of medicinal chemistry, May-22, Volume: 46, Issue:11
Nitro and amino substitution in the D-ring of 5-(2-dimethylaminoethyl)- 2,3-methylenedioxy-5H-dibenzo[c,h][1,6]naphthyridin-6-ones: effect on topoisomerase-I targeting activity and cytotoxicity.
AID248382Concentration required to inhibit cell proliferation in P388/CPT-45 tumor cell line; camptothecin resistant2004Bioorganic & medicinal chemistry letters, Nov-15, Volume: 14, Issue:22
Dimethoxybenzo[i]phenanthridine-12-carboxylic acid derivatives and 6H-dibenzo[c,h][2,6]naphthyridin-5-ones with potent topoisomerase I-targeting activity and cytotoxicity.
AID409905Cytotoxicity against camptothecin-resistant mouse P388 cells by MTT method2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
11-Substituted 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine derivatives as novel topoisomerase I-targeting agents.
AID433915Cytotoxicity against human RPMI8402 cells after 4 days by MTT assay2009European journal of medicinal chemistry, Sep, Volume: 44, Issue:9
Novel topoisomerase I-targeting antitumor agents synthesized from the N,N,N-trimethylammonium derivative of ARC-111, 5H-2,3-dimethoxy-8,9-methylenedioxy-5-[(2-N,N,N-trimethylammonium)ethyl]dibenzo[c,h][1,6]naphthyridin-6-one iodide.
AID46871Cytotoxic activity against human lymphoblast tumor cell line CPT-K5 after 4 days of treatment2003Journal of medicinal chemistry, May-22, Volume: 46, Issue:11
Nitro and amino substitution in the D-ring of 5-(2-dimethylaminoethyl)- 2,3-methylenedioxy-5H-dibenzo[c,h][1,6]naphthyridin-6-ones: effect on topoisomerase-I targeting activity and cytotoxicity.
AID409902Inhibition of human topoisomerase 1 expressed in Escherichia coli assessed as drug level causing 10% mediated DNA cleavage relative to topotecan2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
11-Substituted 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine derivatives as novel topoisomerase I-targeting agents.
AID409903Cytotoxicity against camptothecin-resistant human CPT-K5 cells by MTT method2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
11-Substituted 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine derivatives as novel topoisomerase I-targeting agents.
AID46874Cytotoxicity using camptothecin-resistant variant of RPM18402 (CPT-K5) possessing functional, but mutant TOP-12002Bioorganic & medicinal chemistry letters, Nov-18, Volume: 12, Issue:22
Diaza- and triazachrysenes: potent topoisomerase-targeting agents with exceptional antitumor activity against the human tumor xenograft, MDA-MB-435.
AID331453Cytotoxicity against human camptothecin-resistant P388/CPT45 cells2008Bioorganic & medicinal chemistry letters, Jun-15, Volume: 18, Issue:12
Facile formation of hydrophilic derivatives of 5H-8,9-dimethoxy-5-[2-(N,N-dimethylamino)ethyl]-2,3-methylenedioxydibenzo[c,h] [1,6]naphthyridin-6-one (ARC-111) and its 12-aza analog via quaternary ammonium intermediates.
AID110872In vivo antitumor activity in NCR-nude-nude mice inoculated with 1.2 E6 -1.5 E6 MDA-MB-435 cells after day 21 with an average dose of 0.78 mg/mouse(po)2002Bioorganic & medicinal chemistry letters, Nov-18, Volume: 12, Issue:22
Diaza- and triazachrysenes: potent topoisomerase-targeting agents with exceptional antitumor activity against the human tumor xenograft, MDA-MB-435.
AID248502Inhibitory concentration against camptothecin-resistant variant of P388 cell line was determined2005Journal of medicinal chemistry, Feb-10, Volume: 48, Issue:3
5-(2-aminoethyl)dibenzo[c,h][1,6]naphthyridin-6-ones: variation of n-alkyl substituents modulates sensitivity to efflux transporters associated with multidrug resistance.
AID166892Cytotoxicity against human lymphoblast tumor cell line RPM184022002Bioorganic & medicinal chemistry letters, Nov-18, Volume: 12, Issue:22
Diaza- and triazachrysenes: potent topoisomerase-targeting agents with exceptional antitumor activity against the human tumor xenograft, MDA-MB-435.
AID331451Cytotoxicity against human camptothecin-resistant CPT-K5 cells2008Bioorganic & medicinal chemistry letters, Jun-15, Volume: 18, Issue:12
Facile formation of hydrophilic derivatives of 5H-8,9-dimethoxy-5-[2-(N,N-dimethylamino)ethyl]-2,3-methylenedioxydibenzo[c,h] [1,6]naphthyridin-6-one (ARC-111) and its 12-aza analog via quaternary ammonium intermediates.
AID247760Concentration required to inhibit cell proliferation in KB3-1 tumor cell line2004Bioorganic & medicinal chemistry letters, Nov-15, Volume: 14, Issue:22
Dimethoxybenzo[i]phenanthridine-12-carboxylic acid derivatives and 6H-dibenzo[c,h][2,6]naphthyridin-5-ones with potent topoisomerase I-targeting activity and cytotoxicity.
AID389687Cytotoxicity against camptothecin-resistant and TOP1 deficient mouse P388/CPT45 cells after MTT assay2008Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20
Synthesis of N-substituted 5-[2-(N-alkylamino)ethyl]dibenzo[c,h][1,6]naphthyridines as novel topoisomerase I-targeting antitumor agents.
AID247785Inhibitory concentration against KBH5.0 cells overexpress BCRP2005Journal of medicinal chemistry, Feb-10, Volume: 48, Issue:3
5-(2-aminoethyl)dibenzo[c,h][1,6]naphthyridin-6-ones: variation of n-alkyl substituents modulates sensitivity to efflux transporters associated with multidrug resistance.
AID247815Concentration required to inhibit cell proliferation in RPM18402 tumor cell line2004Bioorganic & medicinal chemistry letters, Nov-15, Volume: 14, Issue:22
Dimethoxybenzo[i]phenanthridine-12-carboxylic acid derivatives and 6H-dibenzo[c,h][2,6]naphthyridin-5-ones with potent topoisomerase I-targeting activity and cytotoxicity.
AID389685Cytotoxicity against camptothecin-resistant human CPT-K5 cells after MTT assay2008Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20
Synthesis of N-substituted 5-[2-(N-alkylamino)ethyl]dibenzo[c,h][1,6]naphthyridines as novel topoisomerase I-targeting antitumor agents.
AID409908Cytotoxicity against human KBH5.0 cells by MTT method2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
11-Substituted 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine derivatives as novel topoisomerase I-targeting agents.
AID247613Cytotoxicity against camptothecin-resistant RPMI 84022005Journal of medicinal chemistry, Feb-10, Volume: 48, Issue:3
5-(2-aminoethyl)dibenzo[c,h][1,6]naphthyridin-6-ones: variation of n-alkyl substituents modulates sensitivity to efflux transporters associated with multidrug resistance.
AID433919Cytotoxicity against human KB3-1 cells after 4 days after MTT assay2009European journal of medicinal chemistry, Sep, Volume: 44, Issue:9
Novel topoisomerase I-targeting antitumor agents synthesized from the N,N,N-trimethylammonium derivative of ARC-111, 5H-2,3-dimethoxy-8,9-methylenedioxy-5-[(2-N,N,N-trimethylammonium)ethyl]dibenzo[c,h][1,6]naphthyridin-6-one iodide.
AID389689Cytotoxicity against multidrug resistant human KBV-1 cells overexpressing MDR1 after MTT assay2008Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20
Synthesis of N-substituted 5-[2-(N-alkylamino)ethyl]dibenzo[c,h][1,6]naphthyridines as novel topoisomerase I-targeting antitumor agents.
AID239852Relative effective concentration to cleave plasmid DNA with human topoisomerase I; compared to camptothecin=12004Bioorganic & medicinal chemistry letters, Nov-15, Volume: 14, Issue:22
Dimethoxybenzo[i]phenanthridine-12-carboxylic acid derivatives and 6H-dibenzo[c,h][2,6]naphthyridin-5-ones with potent topoisomerase I-targeting activity and cytotoxicity.
AID409901Cytotoxicity against human RPMI8402 cells by MTT method2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
11-Substituted 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine derivatives as novel topoisomerase I-targeting agents.
AID362305Cytotoxicity against human multidrug resistant MDR1 overexpressing human KBV1 cells after 4 days by MTT assay2008Bioorganic & medicinal chemistry, Aug-15, Volume: 16, Issue:16
Syntheses and biological evaluation of topoisomerase I-targeting agents related to 11-[2-(N,N-dimethylamino)ethyl]-2,3-dimethoxy-8,9-methylenedioxy-11H-isoquino[4,3-c]cinnolin-12-one (ARC-31).
AID414755Cytotoxicity against camptothecin-resistant human CPT-K5 cells after 4 days by MTT method2009Bioorganic & medicinal chemistry, Apr-01, Volume: 17, Issue:7
12-Substituted 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridines as novel topoisomerase I-targeting antitumor agents.
AID331452Cytotoxicity against human P388 cells2008Bioorganic & medicinal chemistry letters, Jun-15, Volume: 18, Issue:12
Facile formation of hydrophilic derivatives of 5H-8,9-dimethoxy-5-[2-(N,N-dimethylamino)ethyl]-2,3-methylenedioxydibenzo[c,h] [1,6]naphthyridin-6-one (ARC-111) and its 12-aza analog via quaternary ammonium intermediates.
AID414758Cytotoxicity against human KB3-1 cells after 4 days by MTT method2009Bioorganic & medicinal chemistry, Apr-01, Volume: 17, Issue:7
12-Substituted 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridines as novel topoisomerase I-targeting antitumor agents.
AID331450Cytotoxicity against human RPMI-8240 cells2008Bioorganic & medicinal chemistry letters, Jun-15, Volume: 18, Issue:12
Facile formation of hydrophilic derivatives of 5H-8,9-dimethoxy-5-[2-(N,N-dimethylamino)ethyl]-2,3-methylenedioxydibenzo[c,h] [1,6]naphthyridin-6-one (ARC-111) and its 12-aza analog via quaternary ammonium intermediates.
AID433920Cytotoxicity against multidrug resistant human KBV1 cells overexpressing MDR1 after 4 days by MTT assay2009European journal of medicinal chemistry, Sep, Volume: 44, Issue:9
Novel topoisomerase I-targeting antitumor agents synthesized from the N,N,N-trimethylammonium derivative of ARC-111, 5H-2,3-dimethoxy-8,9-methylenedioxy-5-[(2-N,N,N-trimethylammonium)ethyl]dibenzo[c,h][1,6]naphthyridin-6-one iodide.
AID389688Cytotoxicity against human KB3-1 cells after MTT assay2008Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20
Synthesis of N-substituted 5-[2-(N-alkylamino)ethyl]dibenzo[c,h][1,6]naphthyridines as novel topoisomerase I-targeting antitumor agents.
AID110876In vivo antitumor activity in NCR-nude-nude mice inoculated with 1.2 E6 -1.5 E6 MDA-MB-435 cells after day 7 with an average dose of 0.78 mg/mouse (po)2002Bioorganic & medicinal chemistry letters, Nov-18, Volume: 12, Issue:22
Diaza- and triazachrysenes: potent topoisomerase-targeting agents with exceptional antitumor activity against the human tumor xenograft, MDA-MB-435.
AID247812Inhibitory concentration against KB3-1 cell line was determined2005Journal of medicinal chemistry, Feb-10, Volume: 48, Issue:3
5-(2-aminoethyl)dibenzo[c,h][1,6]naphthyridin-6-ones: variation of n-alkyl substituents modulates sensitivity to efflux transporters associated with multidrug resistance.
AID414756Cytotoxicity against mouse P388 cells after 4 days by MTT method2009Bioorganic & medicinal chemistry, Apr-01, Volume: 17, Issue:7
12-Substituted 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridines as novel topoisomerase I-targeting antitumor agents.
AID110869In vivo antitumor activity in NCR-nude-nude mice inoculated with 1.2 E6 -1.5 E6 MDA-MB-435 cells after day 13 with an average dose of 0.73 mg/mouse (ip)2002Bioorganic & medicinal chemistry letters, Nov-18, Volume: 12, Issue:22
Diaza- and triazachrysenes: potent topoisomerase-targeting agents with exceptional antitumor activity against the human tumor xenograft, MDA-MB-435.
AID389885Antitumor activity against human MDA-MB-231 cells xenografted in NCR/NU NU mouse assessed as tumor volume measured on day 49 initially dosed at 1.5 mg/kg, ip qd x 3/5 days schedule2008Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20
Synthesis of N-substituted 5-[2-(N-alkylamino)ethyl]dibenzo[c,h][1,6]naphthyridines as novel topoisomerase I-targeting antitumor agents.
AID414753Inhibition of human topoisomerase 1 expressed in sf9 cells assessed as drug level causing 10% mediated DNA cleavage relative to topotecan2009Bioorganic & medicinal chemistry, Apr-01, Volume: 17, Issue:7
12-Substituted 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridines as novel topoisomerase I-targeting antitumor agents.
AID362304Cytotoxicity against human KB3-1 cells after 4 days by MTT assay2008Bioorganic & medicinal chemistry, Aug-15, Volume: 16, Issue:16
Syntheses and biological evaluation of topoisomerase I-targeting agents related to 11-[2-(N,N-dimethylamino)ethyl]-2,3-dimethoxy-8,9-methylenedioxy-11H-isoquino[4,3-c]cinnolin-12-one (ARC-31).
AID389690Cytotoxicity against multidrug resistant human KBH5.0 cells overexpressing BCRP after MTT assay2008Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20
Synthesis of N-substituted 5-[2-(N-alkylamino)ethyl]dibenzo[c,h][1,6]naphthyridines as novel topoisomerase I-targeting antitumor agents.
AID409904Cytotoxicity against mouse P388 cells by MTT method2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
11-Substituted 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine derivatives as novel topoisomerase I-targeting agents.
AID56881TOP-1 mediated DNA cleavage measured as effective concentration relative to topotecan = 12002Bioorganic & medicinal chemistry letters, Nov-18, Volume: 12, Issue:22
Diaza- and triazachrysenes: potent topoisomerase-targeting agents with exceptional antitumor activity against the human tumor xenograft, MDA-MB-435.
AID56879Concentration relative to topotecan for topoisomerase DNA topoisomerase I cleavage2003Bioorganic & medicinal chemistry letters, Oct-20, Volume: 13, Issue:20
5H-8,9-dimethoxy-5-(2-N,N-dimethylaminoethyl)dibenzo[c,h][1,6]naphthyridin-6-ones and related compounds as TOP1-targeting agents: influence of structure on the ternary cleavable complex formation.
AID389684Cytotoxicity against human RPMI8402 cells after MTT assay2008Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20
Synthesis of N-substituted 5-[2-(N-alkylamino)ethyl]dibenzo[c,h][1,6]naphthyridines as novel topoisomerase I-targeting antitumor agents.
AID110873In vivo antitumor activity in NCR-nude-nude mice inoculated with 1.2 E6 -1.5 E6 MDA-MB-435 cells after day 31 with an average dose of 0.73 mg/mouse (ip)2002Bioorganic & medicinal chemistry letters, Nov-18, Volume: 12, Issue:22
Diaza- and triazachrysenes: potent topoisomerase-targeting agents with exceptional antitumor activity against the human tumor xenograft, MDA-MB-435.
AID414757Cytotoxicity against camptothecin-resistant mouse P388 cells after 4 days by MTT method2009Bioorganic & medicinal chemistry, Apr-01, Volume: 17, Issue:7
12-Substituted 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridines as novel topoisomerase I-targeting antitumor agents.
AID248146Inhibitory concentration against lymphoblast RPMI 8402 cell line was determined2005Journal of medicinal chemistry, Feb-10, Volume: 48, Issue:3
5-(2-aminoethyl)dibenzo[c,h][1,6]naphthyridin-6-ones: variation of n-alkyl substituents modulates sensitivity to efflux transporters associated with multidrug resistance.
AID389883Antitumor activity against human MDA-MB-231 cells xenografted in NCR/NU NU mouse assessed as tumor volume measured on day 35 initially dosed at 1.5 mg/kg, ip qd x 3/5 days schedule2008Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20
Synthesis of N-substituted 5-[2-(N-alkylamino)ethyl]dibenzo[c,h][1,6]naphthyridines as novel topoisomerase I-targeting antitumor agents.
AID362300Cytotoxicity against mouse CPT45-resistant topoisomerase 1-deficient P388 cells after 4 days by MTT assay2008Bioorganic & medicinal chemistry, Aug-15, Volume: 16, Issue:16
Syntheses and biological evaluation of topoisomerase I-targeting agents related to 11-[2-(N,N-dimethylamino)ethyl]-2,3-dimethoxy-8,9-methylenedioxy-11H-isoquino[4,3-c]cinnolin-12-one (ARC-31).
AID57214TOP-2 mediated DNA cleavage measured as effective concentration relative to VM262002Bioorganic & medicinal chemistry letters, Nov-18, Volume: 12, Issue:22
Diaza- and triazachrysenes: potent topoisomerase-targeting agents with exceptional antitumor activity against the human tumor xenograft, MDA-MB-435.
AID389683Inhibition of human topoisomerase 1 mediated DNA cleavage assessed as effective drug concentration causing 10% YepG plasmid cleavage relative to camptothecin2008Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20
Synthesis of N-substituted 5-[2-(N-alkylamino)ethyl]dibenzo[c,h][1,6]naphthyridines as novel topoisomerase I-targeting antitumor agents.
AID433917Cytotoxicity against mouse P388 cells after 4 days by MTT assay2009European journal of medicinal chemistry, Sep, Volume: 44, Issue:9
Novel topoisomerase I-targeting antitumor agents synthesized from the N,N,N-trimethylammonium derivative of ARC-111, 5H-2,3-dimethoxy-8,9-methylenedioxy-5-[(2-N,N,N-trimethylammonium)ethyl]dibenzo[c,h][1,6]naphthyridin-6-one iodide.
AID389879Antitumor activity against human MDA-MB-231 cells xenografted in NCR/NU NU mouse assessed as tumor volume measured on day 7 initially dosed at 1.5 mg/kg, ip qd x 3/5 days schedule2008Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20
Synthesis of N-substituted 5-[2-(N-alkylamino)ethyl]dibenzo[c,h][1,6]naphthyridines as novel topoisomerase I-targeting antitumor agents.
AID389884Antitumor activity against human MDA-MB-231 cells xenografted in NCR/NU NU mouse assessed as tumor volume measured on day 42 initially dosed at 1.5 mg/kg, ip qd x 3/5 days schedule2008Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20
Synthesis of N-substituted 5-[2-(N-alkylamino)ethyl]dibenzo[c,h][1,6]naphthyridines as novel topoisomerase I-targeting antitumor agents.
AID389880Antitumor activity against human MDA-MB-231 cells xenografted in NCR/NU NU mouse assessed as tumor volume measured on day 14 initially dosed at 1.5 mg/kg, ip qd x 3/5 days schedule2008Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20
Synthesis of N-substituted 5-[2-(N-alkylamino)ethyl]dibenzo[c,h][1,6]naphthyridines as novel topoisomerase I-targeting antitumor agents.
AID248252Concentration required to inhibit cell proliferation in CPT-K5 tumor cell line; camptothecin resistant2004Bioorganic & medicinal chemistry letters, Nov-15, Volume: 14, Issue:22
Dimethoxybenzo[i]phenanthridine-12-carboxylic acid derivatives and 6H-dibenzo[c,h][2,6]naphthyridin-5-ones with potent topoisomerase I-targeting activity and cytotoxicity.
AID409907Cytotoxicity against human KBV1 cells by MTT method2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
11-Substituted 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine derivatives as novel topoisomerase I-targeting agents.
AID389882Antitumor activity against human MDA-MB-231 cells xenografted in NCR/NU NU mouse assessed as tumor volume measured on day 28 initially dosed at 1.5 mg/kg, ip qd x 3/5 days schedule2008Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20
Synthesis of N-substituted 5-[2-(N-alkylamino)ethyl]dibenzo[c,h][1,6]naphthyridines as novel topoisomerase I-targeting antitumor agents.
AID414759Cytotoxicity against MDR1 overexpressing human KBV1 cells after 4 days by MTT method2009Bioorganic & medicinal chemistry, Apr-01, Volume: 17, Issue:7
12-Substituted 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridines as novel topoisomerase I-targeting antitumor agents.
AID433916Cytotoxicity against human CPT-K5 cells after 4 days by MTT assay2009European journal of medicinal chemistry, Sep, Volume: 44, Issue:9
Novel topoisomerase I-targeting antitumor agents synthesized from the N,N,N-trimethylammonium derivative of ARC-111, 5H-2,3-dimethoxy-8,9-methylenedioxy-5-[(2-N,N,N-trimethylammonium)ethyl]dibenzo[c,h][1,6]naphthyridin-6-one iodide.
AID110870In vivo antitumor activity in NCR-nude-nude mice inoculated with 1.2 E6 -1.5 E6 MDA-MB-435 cells after day 13 with an average dose of 0.78 mg/mouse (po)2002Bioorganic & medicinal chemistry letters, Nov-18, Volume: 12, Issue:22
Diaza- and triazachrysenes: potent topoisomerase-targeting agents with exceptional antitumor activity against the human tumor xenograft, MDA-MB-435.
AID331449Effect on human topoisomerase 1-mediated plasmid DNA cleavage relative to topotecan2008Bioorganic & medicinal chemistry letters, Jun-15, Volume: 18, Issue:12
Facile formation of hydrophilic derivatives of 5H-8,9-dimethoxy-5-[2-(N,N-dimethylamino)ethyl]-2,3-methylenedioxydibenzo[c,h] [1,6]naphthyridin-6-one (ARC-111) and its 12-aza analog via quaternary ammonium intermediates.
AID248143Inhibitory concentration against P388 cell line in mouse leukemia was determine2005Journal of medicinal chemistry, Feb-10, Volume: 48, Issue:3
5-(2-aminoethyl)dibenzo[c,h][1,6]naphthyridin-6-ones: variation of n-alkyl substituents modulates sensitivity to efflux transporters associated with multidrug resistance.
AID248159Concentration required to inhibit cell proliferation in KBH5.0 tumor cell line; overexpress BCRP2004Bioorganic & medicinal chemistry letters, Nov-15, Volume: 14, Issue:22
Dimethoxybenzo[i]phenanthridine-12-carboxylic acid derivatives and 6H-dibenzo[c,h][2,6]naphthyridin-5-ones with potent topoisomerase I-targeting activity and cytotoxicity.
AID248138Concentration required to inhibit cell proliferation in KBV-1 tumor cell line; overexpress MDR12004Bioorganic & medicinal chemistry letters, Nov-15, Volume: 14, Issue:22
Dimethoxybenzo[i]phenanthridine-12-carboxylic acid derivatives and 6H-dibenzo[c,h][2,6]naphthyridin-5-ones with potent topoisomerase I-targeting activity and cytotoxicity.
AID433918Cytotoxicity against mouse P388/CPT45 cells after 4 days by MTT assay2009European journal of medicinal chemistry, Sep, Volume: 44, Issue:9
Novel topoisomerase I-targeting antitumor agents synthesized from the N,N,N-trimethylammonium derivative of ARC-111, 5H-2,3-dimethoxy-8,9-methylenedioxy-5-[(2-N,N,N-trimethylammonium)ethyl]dibenzo[c,h][1,6]naphthyridin-6-one iodide.
AID414760Cytotoxicity against BCRP overexpressing human KBH5.0 cells after 4 days by MTT method2009Bioorganic & medicinal chemistry, Apr-01, Volume: 17, Issue:7
12-Substituted 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridines as novel topoisomerase I-targeting antitumor agents.
AID110874In vivo antitumor activity in NCR-nude-nude mice inoculated with 1.2 E6 -1.5 E6 MDA-MB-435 cells after day 31 with an average dose of 0.78 mg/mouse (po)2002Bioorganic & medicinal chemistry letters, Nov-18, Volume: 12, Issue:22
Diaza- and triazachrysenes: potent topoisomerase-targeting agents with exceptional antitumor activity against the human tumor xenograft, MDA-MB-435.
AID110871In vivo antitumor activity in NCR-nude-nude mice inoculated with 1.2 E6 -1.5 E6 MDA-MB-435 cells after day 21 with an average dose of 0.73 mg/mouse (ip)2002Bioorganic & medicinal chemistry letters, Nov-18, Volume: 12, Issue:22
Diaza- and triazachrysenes: potent topoisomerase-targeting agents with exceptional antitumor activity against the human tumor xenograft, MDA-MB-435.
AID247744Concentration required to inhibit cell proliferation in P388 tumor cell line2004Bioorganic & medicinal chemistry letters, Nov-15, Volume: 14, Issue:22
Dimethoxybenzo[i]phenanthridine-12-carboxylic acid derivatives and 6H-dibenzo[c,h][2,6]naphthyridin-5-ones with potent topoisomerase I-targeting activity and cytotoxicity.
AID362306Cytotoxicity against human multidrug resistant BCRP overexpressing human KBH5.0 cells after 4 days by MTT assay2008Bioorganic & medicinal chemistry, Aug-15, Volume: 16, Issue:16
Syntheses and biological evaluation of topoisomerase I-targeting agents related to 11-[2-(N,N-dimethylamino)ethyl]-2,3-dimethoxy-8,9-methylenedioxy-11H-isoquino[4,3-c]cinnolin-12-one (ARC-31).
AID362301Inhibition of human topoisomerase 1 expressed in Escherichia coli assessed as YepG plasmid DNA cleavage2008Bioorganic & medicinal chemistry, Aug-15, Volume: 16, Issue:16
Syntheses and biological evaluation of topoisomerase I-targeting agents related to 11-[2-(N,N-dimethylamino)ethyl]-2,3-dimethoxy-8,9-methylenedioxy-11H-isoquino[4,3-c]cinnolin-12-one (ARC-31).
AID167217Cytotoxic activity against human lymphoblast tumor cell line RPMI8402 after 4 days of treatment2003Journal of medicinal chemistry, May-22, Volume: 46, Issue:11
Nitro and amino substitution in the D-ring of 5-(2-dimethylaminoethyl)- 2,3-methylenedioxy-5H-dibenzo[c,h][1,6]naphthyridin-6-ones: effect on topoisomerase-I targeting activity and cytotoxicity.
AID1708540Growth inhibition of ARC-111-resistant human HA6n cells by Cell-titer96 assay2021Journal of medicinal chemistry, 02-11, Volume: 64, Issue:3
Copper(I)-Catalyzed Nitrile-Addition/
AID362302Cytotoxicity against human RPMI8402 cells after 4 days by MTT assay2008Bioorganic & medicinal chemistry, Aug-15, Volume: 16, Issue:16
Syntheses and biological evaluation of topoisomerase I-targeting agents related to 11-[2-(N,N-dimethylamino)ethyl]-2,3-dimethoxy-8,9-methylenedioxy-11H-isoquino[4,3-c]cinnolin-12-one (ARC-31).
AID389686Cytotoxicity against mouse P388 cells after MTT assay2008Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20
Synthesis of N-substituted 5-[2-(N-alkylamino)ethyl]dibenzo[c,h][1,6]naphthyridines as novel topoisomerase I-targeting antitumor agents.
AID362299Cytotoxicity against mouse P388 cells after 4 days by MTT assay2008Bioorganic & medicinal chemistry, Aug-15, Volume: 16, Issue:16
Syntheses and biological evaluation of topoisomerase I-targeting agents related to 11-[2-(N,N-dimethylamino)ethyl]-2,3-dimethoxy-8,9-methylenedioxy-11H-isoquino[4,3-c]cinnolin-12-one (ARC-31).
AID389881Antitumor activity against human MDA-MB-231 cells xenografted in NCR/NU NU mouse assessed as tumor volume measured on day 21 initially dosed at 1.5 mg/kg, ip qd x 3/5 days schedule2008Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20
Synthesis of N-substituted 5-[2-(N-alkylamino)ethyl]dibenzo[c,h][1,6]naphthyridines as novel topoisomerase I-targeting antitumor agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's14 (87.50)29.6817
2010's1 (6.25)24.3611
2020's1 (6.25)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 39.31

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index39.31 (24.57)
Research Supply Index2.83 (2.92)
Research Growth Index4.61 (4.65)
Search Engine Demand Index50.58 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (39.31)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other16 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
camptothecin
NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source		3.75100delta-lactone;
pyranoindolizinoquinoline;
quinoline alkaloid;
tertiary alcohol		antineoplastic agent;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
genotoxin;
plant metabolite
topotecan
Topotecan: An antineoplastic agent used to treat ovarian cancer. It works by inhibiting DNA TOPOISOMERASES, TYPE I.. topotecan : A pyranoindolizinoquinoline used as an antineoplastic agent. It is a derivative of camptothecin and works by binding to the topoisomerase I-DNA complex and preventing religation of these 328 single strand breaks.		3.5380pyranoindolizinoquinolineantineoplastic agent;
EC 5.99.1.2 (DNA topoisomerase) inhibitor
irinotecan
[no description available]		2.9540carbamate ester;
delta-lactone;
N-acylpiperidine;
pyranoindolizinoquinoline;
ring assembly;
tertiary alcohol;
tertiary amino compound		antineoplastic agent;
apoptosis inducer;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
prodrug
sn 38
SN-38 : A member of the class of pyranoindolizinoquinolines that is (4S)-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione bearing two additional ethyl substituents at positions 4 and 11 as well as two additional hydroxy substituents at positions 4 and 9. It is the active metabolite of irinotecan and is ~1000 times more active than irinotecan itself.		2.5220delta-lactone;
phenols;
pyranoindolizinoquinoline;
tertiary alcohol		antineoplastic agent;
apoptosis inducer;
drug metabolite;
EC 5.99.1.2 (DNA topoisomerase) inhibitor
teniposide
[no description available]		2.4220aromatic ether;
beta-D-glucoside;
cyclic acetal;
furonaphthodioxole;
gamma-lactone;
monosaccharide derivative;
phenols;
thiophenes		antineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
arc 31
[no description available]		3.1250
genz-644282
Genz-644282: topoisomerase I-targeting anticancer drug; structure in first source		2.0210
piperidines
Piperidines: A family of hexahydropyridines.		2.0210
ConditionIndicatedRelationship StrengthStudiesTrials
Experimental Neoplasms
[description not available]		02.0110
Breast Cancer
[description not available]		02.0410
Benign Neoplasms
[description not available]		02.0410
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.0410
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		02.0410
Leukemia, Lymphocytic
[description not available]		02.0410
Leukemia, Lymphoid
Leukemia associated with HYPERPLASIA of the lymphoid tissues and increased numbers of circulating malignant LYMPHOCYTES and lymphoblasts.		02.0410
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		02.0410
Weight Reduction
[description not available]		02.0410
Weight Loss
Decrease in existing BODY WEIGHT.		02.0410
Cancer of Colon
[description not available]		02.0110
Bilateral Wilms Tumor
[description not available]		02.0110
Colonic Neoplasms
Tumors or cancer of the COLON.		02.0110
Wilms Tumor
A malignant kidney tumor, caused by the uncontrolled multiplication of renal stem (blastemal), stromal (STROMAL CELLS), and epithelial (EPITHELIAL CELLS) elements. However, not all three are present in every case. Several genes or chromosomal areas have been associated with Wilms tumor which is usually found in childhood as a firm lump in a child's side or ABDOMEN.		02.0110
Anoxemia
[description not available]		02.0310
Hypoxia
Sub-optimal OXYGEN levels in the ambient air of living organisms.		07.0310