Compounds > gwl 78
Page last updated: 2024-11-12

gwl 78

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Cross-References

ID SourceID
PubMed CID16082652
CHEMBL ID215032
SCHEMBL ID22272525
MeSH IDM0523987

Synonyms (11)

Synonym
CHEMBL215032
gwl-78
SCHEMBL22272525
methyl 1-methyl-4-(((1-methyl-4-((1-oxo-4-(((11as)-2,3,5,11a-tetrahydro-7-methoxy-5-oxo-1h-pyrrolo(2,1-c)(1,4)benzodiazepin-8-yl)oxy)butyl)amino)-1h-pyrrol-2-yl)carbonyl)amino)-1h-pyrrole-2-carboxylate
(+)-gwl-78
ahj9fj6lhp ,
1h-pyrrole-2-carboxylic acid, 1-methyl-4-(((1-methyl-4-((1-oxo-4-(((11as)-2,3,5,11a-tetrahydro-7-methoxy-5-oxo-1h-pyrrolo(2,1-c)(1,4)benzodiazepin-8-yl)oxy)butyl)amino)-1h-pyrrol-2-yl)carbonyl)amino)-, methyl ester
unii-ahj9fj6lhp
909415-27-6
gwl78
methyl 4-[[4-[4-[[(6as)-2-methoxy-11-oxo-6a,7,8,9-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-3-yl]oxy]butanoylamino]-1-methylpyrrole-2-carbonyl]amino]-1-methylpyrrole-2-carboxylate
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (55)

Assay IDTitleYearJournalArticle
AID606053Binding affinity to ICB1 site of human topoisomerase 2alpha promoter after 17 hrs by DNase 1 footprinting assay2011Bioorganic & medicinal chemistry letters, Jun-15, Volume: 21, Issue:12
Novel C8-linked pyrrolobenzodiazepine (PBD)-heterocycle conjugates that recognize DNA sequences containing an inverted CCAAT box.
AID688922Binding affinity to 5'-TATA-TGA-TTT-TCA-TATA at 200 uM by HPLC/MS analysis2010ACS medicinal chemistry letters, Nov-11, Volume: 1, Issue:8
DNA Sequence Preference and Adduct Orientation of Pyrrolo[2,1-c][1,4]benzodiazepine Antitumor Agents.
AID270012Cytotoxicity against human K562 cell line after 96 hrs by MTT assay2006Journal of medicinal chemistry, Sep-07, Volume: 49, Issue:18
Design, synthesis, and biophysical and biological evaluation of a series of pyrrolobenzodiazepine-poly(N-methylpyrrole) conjugates.
AID270009Inhibition of DNA transcription at 5 uM2006Journal of medicinal chemistry, Sep-07, Volume: 49, Issue:18
Design, synthesis, and biophysical and biological evaluation of a series of pyrrolobenzodiazepine-poly(N-methylpyrrole) conjugates.
AID728943Cytotoxicity against human primary CLL cells after 96 hrs by annexin V/propidium iodide staining-based FACS flow cytometric analysis2013Journal of medicinal chemistry, Apr-11, Volume: 56, Issue:7
GC-targeted C8-linked pyrrolobenzodiazepine-biaryl conjugates with femtomolar in vitro cytotoxicity and in vivo antitumor activity in mouse models.
AID688924Binding affinity to 5'-TGT-TATA-TTT-TATA-ACA at 200 uM by HPLC/MS analysis2010ACS medicinal chemistry letters, Nov-11, Volume: 1, Issue:8
DNA Sequence Preference and Adduct Orientation of Pyrrolo[2,1-c][1,4]benzodiazepine Antitumor Agents.
AID728854Cytotoxicity against human A431 cells after 96 hrs by MTT assay2013Journal of medicinal chemistry, Apr-11, Volume: 56, Issue:7
GC-targeted C8-linked pyrrolobenzodiazepine-biaryl conjugates with femtomolar in vitro cytotoxicity and in vivo antitumor activity in mouse models.
AID728942Cytotoxicity against human MIAPaCa2 cells after 96 hrs by MTT assay2013Journal of medicinal chemistry, Apr-11, Volume: 56, Issue:7
GC-targeted C8-linked pyrrolobenzodiazepine-biaryl conjugates with femtomolar in vitro cytotoxicity and in vivo antitumor activity in mouse models.
AID1853116Binding affinity to AT-rich 5'-fluoro and 3'-TAMRA tagged 5'-TAT-ATA-TAG-ATA-TTT-TTT-TAT-CTA-TAT-ATA-3' hairpin DNA(unknown origin) assessed as thermal stabilization by measuring change in melting temperature at 1 uM incubated for 24 hrs by FRET analysis2022RSC medicinal chemistry, Dec-14, Volume: 13, Issue:12
Mechanistic insight into the repair of C8-linked pyrrolobenzodiazepine monomer-mediated DNA damage.
AID688921Binding affinity to 5'-TATA-AGT-TTT-ACT-TATA at 200 uM by HPLC/MS analysis2010ACS medicinal chemistry letters, Nov-11, Volume: 1, Issue:8
DNA Sequence Preference and Adduct Orientation of Pyrrolo[2,1-c][1,4]benzodiazepine Antitumor Agents.
AID1652597Antimicrobial activity against Klebsiella pneumoniae M6 by microdilution broth method
AID270008Cytotoxicity against human NCI60 cell line by MTT assay2006Journal of medicinal chemistry, Sep-07, Volume: 49, Issue:18
Design, synthesis, and biophysical and biological evaluation of a series of pyrrolobenzodiazepine-poly(N-methylpyrrole) conjugates.
AID728855Cytotoxicity against human A549 cells after 96 hrs by MTT assay2013Journal of medicinal chemistry, Apr-11, Volume: 56, Issue:7
GC-targeted C8-linked pyrrolobenzodiazepine-biaryl conjugates with femtomolar in vitro cytotoxicity and in vivo antitumor activity in mouse models.
AID1652595Antimicrobial activity against multidrug-resistant Acinetobacter baumannii AYE by microdilution broth method
AID1652600Antimicrobial activity against Pseudomonas aeruginosa PAO1 by microdilution broth method
AID606055Cytotoxicity against human NCI60 cells2011Bioorganic & medicinal chemistry letters, Jun-15, Volume: 21, Issue:12
Novel C8-linked pyrrolobenzodiazepine (PBD)-heterocycle conjugates that recognize DNA sequences containing an inverted CCAAT box.
AID1652607Antibacterial activity against methicillin sensitive Staphylococcus aureus NCTC 6571 by microdilution broth method
AID728851Binding affinity to AT-rich FAM-TATAAGATTTTCTTATA-TAMRA DNA (unknown origin) assessed as change in melting temperature at 1 uM by FRET assay2013Journal of medicinal chemistry, Apr-11, Volume: 56, Issue:7
GC-targeted C8-linked pyrrolobenzodiazepine-biaryl conjugates with femtomolar in vitro cytotoxicity and in vivo antitumor activity in mouse models.
AID1853118Binding affinity to GC-rich 5'-fluoro and 3'-TAMRA tagged 5'-TAT-AGG-GAC-AGC-CCT-ATA-3' hairpin DNA (unknown origin) assessed as thermal stabilization by measuring change in melting temperature at 1 uM incubated for 24 hrs by FRET analysis2022RSC medicinal chemistry, Dec-14, Volume: 13, Issue:12
Mechanistic insight into the repair of C8-linked pyrrolobenzodiazepine monomer-mediated DNA damage.
AID606052Binding affinity to calf thymus DNA assessed as change in melting temperature at 5 uM at pH 7 after 18 hrs by thermal denaturation assay2011Bioorganic & medicinal chemistry letters, Jun-15, Volume: 21, Issue:12
Novel C8-linked pyrrolobenzodiazepine (PBD)-heterocycle conjugates that recognize DNA sequences containing an inverted CCAAT box.
AID728857Binding affinity to AT-rich TATA-AGA-TTT-TCT-TATA DNA (unknown origin) after 5 mins by HPLC-MS analysis (Rvb = 70 %)2013Journal of medicinal chemistry, Apr-11, Volume: 56, Issue:7
GC-targeted C8-linked pyrrolobenzodiazepine-biaryl conjugates with femtomolar in vitro cytotoxicity and in vivo antitumor activity in mouse models.
AID1652606Antibacterial activity against methicillin resistant Staphylococcus aureus NCTC 13277 by microdilution broth method
AID1652687Stabilization of 5'-FAM-TAT-AGA-TAT-AGA-TAT-TTT-ATA-TCT-ATA-TCT-ATA-3'-TAMRA DNA (unknown origin) assessed as reduction in change in melting temperature at 1:1 to 5:1 ligand to DNA ratio measured after 3 hrs by FRET-based assay relative to control
AID728939Cytotoxicity against human WI38 cells after 96 hrs by MTT assay2013Journal of medicinal chemistry, Apr-11, Volume: 56, Issue:7
GC-targeted C8-linked pyrrolobenzodiazepine-biaryl conjugates with femtomolar in vitro cytotoxicity and in vivo antitumor activity in mouse models.
AID1614600Cytotoxicity against human JJN-3 cells assessed as cell death after 48 hrs by annexin V/propidium iodide-staining based flow cytometry2019Journal of medicinal chemistry, 02-28, Volume: 62, Issue:4
Effects of Systematic Shortening of Noncovalent C8 Side Chain on the Cytotoxicity and NF-κB Inhibitory Capacity of Pyrrolobenzodiazepines (PBDs).
AID766124Binding affinity to topo 2-alpha ICB1 (5'-CAGGGATTGGCTGGT-3') in mouse NIH/3T3 cells nuclear extract assessed as inhibition of NF-Y transcription factor binding at 5 uM preincubated for 1.5 hrs and by electrophoretic mobility shift assay2013Journal of medicinal chemistry, Aug-22, Volume: 56, Issue:16
An extended pyrrolobenzodiazepine-polyamide conjugate with selectivity for a DNA sequence containing the ICB2 transcription factor binding site.
AID1652686Stabilization of 5'-FAM-TAT-ATA-TAG-ATA-TTT-TTT-TAT-CTA-TAT-ATA-3'-TAMRA DNA (unknown origin) assessed as reduction in change in melting temperature at 1:1 to 5:1 ligand to DNA ratio measured after 3 hrs by FRET-based assay relative to control
AID688925Binding affinity to 5'-AGT-TATA-TTT-TATA-ACT at 200 uM by HPLC/MS analysis2010ACS medicinal chemistry letters, Nov-11, Volume: 1, Issue:8
DNA Sequence Preference and Adduct Orientation of Pyrrolo[2,1-c][1,4]benzodiazepine Antitumor Agents.
AID1652603Antibacterial activity against vancomycin resistant Enterococcus faecalis NCTC 12201 by microdilution broth method
AID1652604Antibacterial activity against vancomycin sensitive Enterococcus faecalis NCTC 775 by microdilution broth method
AID1853115Binding affinity to AT-rich 5'-fluoro and 3'-TAMRA tagged 5'-TAT-ATA-TAG-ATA-TTT-TTT-TAT-CTA-TAT-ATA-3' hairpin DNA (unknown origin) assessed as thermal stabilization by measuring change in melting temperature at 1 uM incubated for 3 hrs by FRET analysis2022RSC medicinal chemistry, Dec-14, Volume: 13, Issue:12
Mechanistic insight into the repair of C8-linked pyrrolobenzodiazepine monomer-mediated DNA damage.
AID688807Binding affinity to 5'-TATA-AGA-TTT-TCT-TATA at 200 uM by HPLC/MS analysis2010ACS medicinal chemistry letters, Nov-11, Volume: 1, Issue:8
DNA Sequence Preference and Adduct Orientation of Pyrrolo[2,1-c][1,4]benzodiazepine Antitumor Agents.
AID1652599Antimicrobial activity against multidrug-resistant Klebsiella pneumoniae NCTC 13368 by microdilution broth method
AID728852Binding affinity to GC-rich GCGC-AGA-TTT-TCT-GCGC DNA (unknown origin) after 5 mins by HPLC-MS analysis (Rvb = 12 %)2013Journal of medicinal chemistry, Apr-11, Volume: 56, Issue:7
GC-targeted C8-linked pyrrolobenzodiazepine-biaryl conjugates with femtomolar in vitro cytotoxicity and in vivo antitumor activity in mouse models.
AID766127Binding affinity to 170 bp human DNA topoisomerase 2-alpha promoter ICB2 site at 1 uM after 17 hrs by DNase 1 footprinting assay2013Journal of medicinal chemistry, Aug-22, Volume: 56, Issue:16
An extended pyrrolobenzodiazepine-polyamide conjugate with selectivity for a DNA sequence containing the ICB2 transcription factor binding site.
AID688808Binding affinity to 5'-TATA-TGT-TTT-ACA-TATA at 200 uM by HPLC/MS analysis2010ACS medicinal chemistry letters, Nov-11, Volume: 1, Issue:8
DNA Sequence Preference and Adduct Orientation of Pyrrolo[2,1-c][1,4]benzodiazepine Antitumor Agents.
AID728940Cytotoxicity against human MCF7 cells after 96 hrs by MTT assay2013Journal of medicinal chemistry, Apr-11, Volume: 56, Issue:7
GC-targeted C8-linked pyrrolobenzodiazepine-biaryl conjugates with femtomolar in vitro cytotoxicity and in vivo antitumor activity in mouse models.
AID766125Binding affinity to topo 2-alpha ICB2 (5'-CTACGATTGGTTCTT-3') in mouse NIH/3T3 cells nuclear extract assessed as inhibition of NF-Y transcription factor binding at 5 uM preincubated for 1.5 hrs by electrophoretic mobility shift assay2013Journal of medicinal chemistry, Aug-22, Volume: 56, Issue:16
An extended pyrrolobenzodiazepine-polyamide conjugate with selectivity for a DNA sequence containing the ICB2 transcription factor binding site.
AID1652594Antimicrobial activity against Acinetobacter baumannii ATCC 17978 by microdilution broth method
AID1652602Antibacterial activity against vancomycin resistant Enterococcus faecium NCTC 12204 by microdilution broth method
AID688923Binding affinity to 5'-AGA-TATA-TTT-TATA-TCT at 200 uM by HPLC/MS analysis2010ACS medicinal chemistry letters, Nov-11, Volume: 1, Issue:8
DNA Sequence Preference and Adduct Orientation of Pyrrolo[2,1-c][1,4]benzodiazepine Antitumor Agents.
AID728944Cytotoxicity against human A2780 cells after 96 hrs by MTT assay2013Journal of medicinal chemistry, Apr-11, Volume: 56, Issue:7
GC-targeted C8-linked pyrrolobenzodiazepine-biaryl conjugates with femtomolar in vitro cytotoxicity and in vivo antitumor activity in mouse models.
AID606054Binding affinity to ICB2 site of human topoisomerase 2alpha promoter after 17 hrs by DNase 1 footprinting assay2011Bioorganic & medicinal chemistry letters, Jun-15, Volume: 21, Issue:12
Novel C8-linked pyrrolobenzodiazepine (PBD)-heterocycle conjugates that recognize DNA sequences containing an inverted CCAAT box.
AID766122Binding affinity to 170 bp human DNA topoisomerase 2-alpha promoter ICB1 site at 1 uM after 17 hrs by DNase 1 footprinting assay2013Journal of medicinal chemistry, Aug-22, Volume: 56, Issue:16
An extended pyrrolobenzodiazepine-polyamide conjugate with selectivity for a DNA sequence containing the ICB2 transcription factor binding site.
AID1853117Binding affinity to GC-rich 5'-fluoro and 3'-TAMRA tagged 5'-TAT-AGG-GAC-AGC-CCT-ATA-3' hairpin DNA (unknown origin) assessed as thermal stabilization by measuring change in melting temperature at 1 uM incubated for 3 hrs by FRET analysis2022RSC medicinal chemistry, Dec-14, Volume: 13, Issue:12
Mechanistic insight into the repair of C8-linked pyrrolobenzodiazepine monomer-mediated DNA damage.
AID270010Uptake in human MCF7 cells at 100 uM after 24 hrs2006Journal of medicinal chemistry, Sep-07, Volume: 49, Issue:18
Design, synthesis, and biophysical and biological evaluation of a series of pyrrolobenzodiazepine-poly(N-methylpyrrole) conjugates.
AID728850Binding affinity to GC-rich FAM-GCGCAGATTTTCTGCGC-TAMRA DNA (unknown origin) assessed as change in melting temperature at 1 uM by FRET assay2013Journal of medicinal chemistry, Apr-11, Volume: 56, Issue:7
GC-targeted C8-linked pyrrolobenzodiazepine-biaryl conjugates with femtomolar in vitro cytotoxicity and in vivo antitumor activity in mouse models.
AID606051Binding affinity to calf thymus DNA assessed as change in melting temperature at 5 uM at pH 7 after 4 hrs by thermal denaturation assay2011Bioorganic & medicinal chemistry letters, Jun-15, Volume: 21, Issue:12
Novel C8-linked pyrrolobenzodiazepine (PBD)-heterocycle conjugates that recognize DNA sequences containing an inverted CCAAT box.
AID728853Selectivity ratio of deltaTm for GC-rich FAM-GCGCAGATTTTCTGCGC-TAMRA DNA (unknown origin) to deltaTm for AT-rich FAM-TATAAGATTTTCTTATA-TAMRA DNA (unknown origin)2013Journal of medicinal chemistry, Apr-11, Volume: 56, Issue:7
GC-targeted C8-linked pyrrolobenzodiazepine-biaryl conjugates with femtomolar in vitro cytotoxicity and in vivo antitumor activity in mouse models.
AID1614599Cytotoxicity against human primary CLL cells assessed as cell death after 48 hrs by annexin V/propidium iodide-staining based flow cytometry2019Journal of medicinal chemistry, 02-28, Volume: 62, Issue:4
Effects of Systematic Shortening of Noncovalent C8 Side Chain on the Cytotoxicity and NF-κB Inhibitory Capacity of Pyrrolobenzodiazepines (PBDs).
AID1652605Antibacterial activity against methicillin resistant Staphylococcus aureus NCTC 13616 by microdilution broth method
AID728941Cytotoxicity against human MDA-MB-231 cells after 96 hrs by MTT assay2013Journal of medicinal chemistry, Apr-11, Volume: 56, Issue:7
GC-targeted C8-linked pyrrolobenzodiazepine-biaryl conjugates with femtomolar in vitro cytotoxicity and in vivo antitumor activity in mouse models.
AID1652601Antimicrobial activity against multidrug-resistant Pseudomonas aeruginosa NCTC 13437 by microdilution broth method
AID1652688Cytotoxicity against human WI38 cells assessed as cell viability at 20 uM measured after 24 hrs by MTT assay relative to control
AID688926Binding affinity to 5'-TGA-TATA-TTT-TATA-TCA at 200 uM by HPLC/MS analysis2010ACS medicinal chemistry letters, Nov-11, Volume: 1, Issue:8
DNA Sequence Preference and Adduct Orientation of Pyrrolo[2,1-c][1,4]benzodiazepine Antitumor Agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (12.50)29.6817
2010's5 (62.50)24.3611
2020's2 (25.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
methyl methanesulfonate
[no description available]		2.4110methanesulfonate esteralkylating agent;
apoptosis inducer;
carcinogenic agent;
genotoxin;
mutagen
norfloxacin
Norfloxacin: A synthetic fluoroquinolone (FLUOROQUINOLONES) with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin inhibits bacterial DNA GYRASE.. norfloxacin : A quinolinemonocarboxylic acid with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase.		2.4110fluoroquinolone antibiotic;
N-arylpiperazine;
quinolinemonocarboxylic acid;
quinolone antibiotic;
quinolone		antibacterial drug;
DNA synthesis inhibitor;
environmental contaminant;
xenobiotic
mitomycin
Mitomycin: An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional ALKYLATING AGENTS causing cross-linking of DNA and inhibition of DNA synthesis.. mitomycin : A family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.		2.4110mitomycinalkylating agent;
antineoplastic agent
sjg 136
1,1'-((propane-1,3-diyl)dioxy)bis(7-methoxy-2-methylidene-1,2,3,10,11,11a-hexahydro-5H-pyrrolo(2,1-c)(1,4)benzodiazepin-5,11-dione): structure in first source		2.0310
ConditionIndicatedRelationship StrengthStudiesTrials
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.0810