Compounds > dsb 120
Page last updated: 2024-11-11

dsb 120

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Cross-References

ID SourceID
PubMed CID9849976
CHEMBL ID279754
SCHEMBL ID16804809
MeSH IDM0236867

Synonyms (6)

Synonym
CHEMBL279754
dsb-120
140676-21-7
(s-(r*,r*))-8,8'-(1,3-propanediylbis(oxy))bis(1,2,3,11a-tetrahydro-7-methoxy-5h-pyrrolo(2,1-c)(1,4)benzodiazepin-5-one
SCHEMBL16804809
(6as)-3-[3-[[(6as)-2-methoxy-11-oxo-6a,7,8,9-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-3-yl]oxy]propoxy]-2-methoxy-6a,7,8,9-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-11-one
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (57)

Assay IDTitleYearJournalArticle
AID41579Compound was tested for inhibition of restriction endonuclease BamH1 enzyme at a concentration of 25 uM;Inhibited2004Journal of medicinal chemistry, Feb-26, Volume: 47, Issue:5
Linker length modulates DNA cross-linking reactivity and cytotoxic potency of C8/C8' ether-linked C2-exo-unsaturated pyrrolo[2,1-c][1,4]benzodiazepine (PBD) dimers.
AID366083Binding affinity to calf thymus DNA assessed as helix melting temperature at 20 uM after 18 hrs by thermal denaturation assay2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Remarkable DNA binding affinity and potential anticancer activity of pyrrolo[2,1-c][1,4]benzodiazepine-naphthalimide conjugates linked through piperazine side-armed alkane spacers.
AID10016Dose of required to inhibit growth of cisplatin resistant human ovarian carcinoma (A2780 cisR) cell line with compound free controls as measured by the sulforhodamine B growth delay assay2001Bioorganic & medicinal chemistry letters, Nov-05, Volume: 11, Issue:21
Synthesis of the first example of a C2-C3/C2'-C3'-endo unsaturated pyrrolo[2,1-c][1,4]benzodiazepine dimer.
AID10018Growth inhibition in human ovarian carcinoma cell line (A2780cisR,cisplatin-resistant) using the 96 hour exposure sulforhodamine B (SRB) growth delay assay2001Journal of medicinal chemistry, Mar-01, Volume: 44, Issue:5
Design, synthesis, and evaluation of a novel pyrrolobenzodiazepine DNA-interactive agent with highly efficient cross-linking ability and potent cytotoxicity.
AID67626In vitro cellular toxicity against murine mammary carcinoma EMT6 cell line after 4 hr of compound exposure2003Journal of medicinal chemistry, May-22, Volume: 46, Issue:11
Unsymmetrical DNA cross-linking agents: combination of the CBI and PBD pharmacophores.
AID47512Inhibition of cell growth in human ovarian carcinoma cell line (CH1) was determined using the 96 hour continuous exposure sulforhodamine B (SRB) growth delay assay.2001Journal of medicinal chemistry, Mar-01, Volume: 44, Issue:5
Design, synthesis, and evaluation of a novel pyrrolobenzodiazepine DNA-interactive agent with highly efficient cross-linking ability and potent cytotoxicity.
AID54323Thermal stabilization of duplex form of calf thymus DNA after incubation for 0 hours2004Journal of medicinal chemistry, Feb-26, Volume: 47, Issue:5
Linker length modulates DNA cross-linking reactivity and cytotoxic potency of C8/C8' ether-linked C2-exo-unsaturated pyrrolo[2,1-c][1,4]benzodiazepine (PBD) dimers.
AID45978Thermal denaturation measured for calf thymus DNA after incubation at 37 degree at 18 h.2002Journal of medicinal chemistry, Oct-10, Volume: 45, Issue:21
Design, synthesis, and evaluation of new noncross-linking pyrrolobenzodiazepine dimers with efficient DNA binding ability and potent antitumor activity.
AID94817Inhibitory concentration against human K562 leukemia cells following incubation for 1 hour2004Journal of medicinal chemistry, Feb-26, Volume: 47, Issue:5
Linker length modulates DNA cross-linking reactivity and cytotoxic potency of C8/C8' ether-linked C2-exo-unsaturated pyrrolo[2,1-c][1,4]benzodiazepine (PBD) dimers.
AID54420DNA binding ability by thermal denaturation studies using calf thymus DNA after incubation at 37 degree C for 18 hour2004Bioorganic & medicinal chemistry letters, May-17, Volume: 14, Issue:10
The effect of C2-fluoro group on the biological activity of DC-81 and its dimers.
AID54325Thermal stabilization of duplex form of calf thymus DNA after incubation for 4 hours2004Journal of medicinal chemistry, Feb-26, Volume: 47, Issue:5
Linker length modulates DNA cross-linking reactivity and cytotoxic potency of C8/C8' ether-linked C2-exo-unsaturated pyrrolo[2,1-c][1,4]benzodiazepine (PBD) dimers.
AID249981Increase in melting point temperature after 36 hr of incubation [1:5] as measurement of DNA binding affinity using calf thymus DNA2004Bioorganic & medicinal chemistry letters, Nov-15, Volume: 14, Issue:22
Synthesis of fluorinated analogues of SJG-136 and their DNA-binding potential.
AID305370Binding affinity to calf thymus DNA at 1:5 (compound:DNA) molar ratio in pH 7.0, 37 degC after 18 hrs by thermal denaturation study2007Bioorganic & medicinal chemistry letters, Feb-01, Volume: 17, Issue:3
Synthesis and DNA-binding ability of C2R-fluoro substituted DC-81 and its dimers.
AID46317Effect on thermal denaturation temperature of CT-DNA after incubation for 18 hours with the compound1999Journal of medicinal chemistry, Oct-07, Volume: 42, Issue:20
Design, synthesis, and evaluation of a novel sequence-selective epoxide-containing DNA cross-linking agent based on the pyrrolo[2, 1-c][1,4]benzodiazepine system.
AID249980Increase in melting point temperature after 18 hr of incubation [1:5] as measurement of DNA binding affinity using calf thymus DNA2004Bioorganic & medicinal chemistry letters, Nov-15, Volume: 14, Issue:22
Synthesis of fluorinated analogues of SJG-136 and their DNA-binding potential.
AID203351In vitro cytotoxicity against human tumor SiHa cell line was measured as concentration to reduce [3H]thymidine uptake to 50% of that of the controls2003Journal of medicinal chemistry, May-22, Volume: 46, Issue:11
Unsymmetrical DNA cross-linking agents: combination of the CBI and PBD pharmacophores.
AID305371Binding affinity to calf thymus DNA at 1:5 (compound:DNA) molar ratio in pH 7.0, 37 degC after 18 hrs by thermal denaturation study2007Bioorganic & medicinal chemistry letters, Feb-01, Volume: 17, Issue:3
Synthesis and DNA-binding ability of C2R-fluoro substituted DC-81 and its dimers.
AID84448In vitro cytotoxicity against human tumor HT-29 cell line was measured as concentration to reduce [3H]thymidine uptake to 50% of that of the controls2003Journal of medicinal chemistry, May-22, Volume: 46, Issue:11
Unsymmetrical DNA cross-linking agents: combination of the CBI and PBD pharmacophores.
AID224921Tested for its ability to cross-link linearized plasmid DNA pcDNA3 following 18 hr of exposure at 37 degree celsius2003Journal of medicinal chemistry, May-22, Volume: 46, Issue:11
Unsymmetrical DNA cross-linking agents: combination of the CBI and PBD pharmacophores.
AID47506In vitro cytotoxicity against ovarian carcinoma cell line CH1.1999Journal of medicinal chemistry, Oct-07, Volume: 42, Issue:20
Design, synthesis, and evaluation of a novel sequence-selective epoxide-containing DNA cross-linking agent based on the pyrrolo[2, 1-c][1,4]benzodiazepine system.
AID46318Effect on thermal denaturation temperature of CT-DNA after incubation for 36 hours with the compound1999Journal of medicinal chemistry, Oct-07, Volume: 42, Issue:20
Design, synthesis, and evaluation of a novel sequence-selective epoxide-containing DNA cross-linking agent based on the pyrrolo[2, 1-c][1,4]benzodiazepine system.
AID202838Inhibition of cell growth in human ovarian carcinoma cell line(SKOV-3) using the 96 hour continuous exposure sulforhodamine B (SRB) growth delay assay2001Journal of medicinal chemistry, Mar-01, Volume: 44, Issue:5
Design, synthesis, and evaluation of a novel pyrrolobenzodiazepine DNA-interactive agent with highly efficient cross-linking ability and potent cytotoxicity.
AID258718Cytotoxicity against LS174T human colon cell line after continuous exposure2006Bioorganic & medicinal chemistry letters, Jan-15, Volume: 16, Issue:2
Synthesis and biological evaluation of novel pyrrolo[2,1-c][1,4]benzodiazepine prodrugs for use in antibody-directed enzyme prodrug therapy.
AID392957Binding affinity to calf thymus DNA assessed as change in melting temperature at a compound to DNA molar ratio of 1:5 at pH 7 by thermal denaturation assay2009Bioorganic & medicinal chemistry, Feb-15, Volume: 17, Issue:4
Remarkable enhancement in the DNA-binding ability of C2-fluoro substituted pyrrolo[2,1-c][1,4]benzodiazepines and their anticancer potential.
AID47507In vitro cytotoxicity against. ovarian carcinoma cell line CH1cisR (cisplatin resistant counter part of CH1).1999Journal of medicinal chemistry, Oct-07, Volume: 42, Issue:20
Design, synthesis, and evaluation of a novel sequence-selective epoxide-containing DNA cross-linking agent based on the pyrrolo[2, 1-c][1,4]benzodiazepine system.
AID54280DNA binding ability by thermal denaturation studies using calf thymus DNA after incubation at 37 degree C for 0 hour2004Bioorganic & medicinal chemistry letters, May-17, Volume: 14, Issue:10
The effect of C2-fluoro group on the biological activity of DC-81 and its dimers.
AID1367554Antiproliferative activity against human NCI-H226 cells after 72 hrs by MTS assay2017Bioorganic & medicinal chemistry letters, 12-01, Volume: 27, Issue:23
Macrocyclic pyrrolobenzodiazepine dimers as antibody-drug conjugate payloads.
AID202972In vitro cytotoxicity against. ovarian carcinoma cell line SKOV-3.1999Journal of medicinal chemistry, Oct-07, Volume: 42, Issue:20
Design, synthesis, and evaluation of a novel sequence-selective epoxide-containing DNA cross-linking agent based on the pyrrolo[2, 1-c][1,4]benzodiazepine system.
AID1367555Antiproliferative activity against human NCI-N87 cells after 72 hrs by MTS assay2017Bioorganic & medicinal chemistry letters, 12-01, Volume: 27, Issue:23
Macrocyclic pyrrolobenzodiazepine dimers as antibody-drug conjugate payloads.
AID46319Effect on thermal denaturation temperature of CT-DNA after incubation for 4 hours with the compound1999Journal of medicinal chemistry, Oct-07, Volume: 42, Issue:20
Design, synthesis, and evaluation of a novel sequence-selective epoxide-containing DNA cross-linking agent based on the pyrrolo[2, 1-c][1,4]benzodiazepine system.
AID9821Inhibition of cell growth in human ovarian carcinoma cell line (A2780) using the 96 hour continuous exposure sulforhodamine B (SRB) growth delay assay2001Journal of medicinal chemistry, Mar-01, Volume: 44, Issue:5
Design, synthesis, and evaluation of a novel pyrrolobenzodiazepine DNA-interactive agent with highly efficient cross-linking ability and potent cytotoxicity.
AID47514Inhibition of cell growth in human ovarian carcinoma cell line (CH1-cis-R,cisplatin resistant) using the 96 hour continuous exposure sulforhodamine B (SRB) growth delay assay2001Journal of medicinal chemistry, Mar-01, Volume: 44, Issue:5
Design, synthesis, and evaluation of a novel pyrrolobenzodiazepine DNA-interactive agent with highly efficient cross-linking ability and potent cytotoxicity.
AID230366Resistance factor (IC50 resistant/ parent)2001Bioorganic & medicinal chemistry letters, Nov-05, Volume: 11, Issue:21
Synthesis of the first example of a C2-C3/C2'-C3'-endo unsaturated pyrrolo[2,1-c][1,4]benzodiazepine dimer.
AID9648In vitro cellular toxicity against chinese hamster AA8 cell line after 4 hr of compound exposure2003Journal of medicinal chemistry, May-22, Volume: 46, Issue:11
Unsymmetrical DNA cross-linking agents: combination of the CBI and PBD pharmacophores.
AID115127In vivo maximum tolerated dose for single intraperitoneal injection in non tumor-bearing C3H/HeN mice2003Journal of medicinal chemistry, May-22, Volume: 46, Issue:11
Unsymmetrical DNA cross-linking agents: combination of the CBI and PBD pharmacophores.
AID10172In vitro cytotoxicity against. ovarian carcinoma cell line A2780cisR (cisplatin resistant counter part of A2780).1999Journal of medicinal chemistry, Oct-07, Volume: 42, Issue:20
Design, synthesis, and evaluation of a novel sequence-selective epoxide-containing DNA cross-linking agent based on the pyrrolo[2, 1-c][1,4]benzodiazepine system.
AID224602Compound dose required to induce 50 percent cross linking in naked plasmid pBR322 DNA following incubation with agent for 2 hours at 37 degree C2004Journal of medicinal chemistry, Feb-26, Volume: 47, Issue:5
Linker length modulates DNA cross-linking reactivity and cytotoxic potency of C8/C8' ether-linked C2-exo-unsaturated pyrrolo[2,1-c][1,4]benzodiazepine (PBD) dimers.
AID54324Thermal stabilization of duplex form of calf thymus DNA after incubation for 18 hours2004Journal of medicinal chemistry, Feb-26, Volume: 47, Issue:5
Linker length modulates DNA cross-linking reactivity and cytotoxic potency of C8/C8' ether-linked C2-exo-unsaturated pyrrolo[2,1-c][1,4]benzodiazepine (PBD) dimers.
AID10017Dose of required to inhibit growth of human ovarian carcinoma (A2780) cell line with compound free controls as measured by the sulforhodamine B growth delay assay2001Bioorganic & medicinal chemistry letters, Nov-05, Volume: 11, Issue:21
Synthesis of the first example of a C2-C3/C2'-C3'-endo unsaturated pyrrolo[2,1-c][1,4]benzodiazepine dimer.
AID10171In vitro cytotoxicity against. ovarian carcinoma cell line A2780.1999Journal of medicinal chemistry, Oct-07, Volume: 42, Issue:20
Design, synthesis, and evaluation of a novel sequence-selective epoxide-containing DNA cross-linking agent based on the pyrrolo[2, 1-c][1,4]benzodiazepine system.
AID94467Inhibition of cell growth by 50% in human leukemia cell line (K562) was determined using microculture tetrazolium (MTT) assay.2001Journal of medicinal chemistry, Mar-01, Volume: 44, Issue:5
Design, synthesis, and evaluation of a novel pyrrolobenzodiazepine DNA-interactive agent with highly efficient cross-linking ability and potent cytotoxicity.
AID46316Effect on thermal denaturation temperature of CT-DNA after incubation for 0 hours with the compound1999Journal of medicinal chemistry, Oct-07, Volume: 42, Issue:20
Design, synthesis, and evaluation of a novel sequence-selective epoxide-containing DNA cross-linking agent based on the pyrrolo[2, 1-c][1,4]benzodiazepine system.
AID216590In vitro cytotoxicity against human tumor WiDr cell line was measured as concentration to reduce [3H]thymidine uptake to 50% of that of the controls2003Journal of medicinal chemistry, May-22, Volume: 46, Issue:11
Unsymmetrical DNA cross-linking agents: combination of the CBI and PBD pharmacophores.
AID232613Ratio of IC50 against human ovarian carcinoma cell line (CH1)cisR (cisplatin resistant) to the IC50 of parent2001Journal of medicinal chemistry, Mar-01, Volume: 44, Issue:5
Design, synthesis, and evaluation of a novel pyrrolobenzodiazepine DNA-interactive agent with highly efficient cross-linking ability and potent cytotoxicity.
AID115128In vivo maximum tolerated dose for single intravenous injection in non-tumor-bearing C3H/HeN mice2003Journal of medicinal chemistry, May-22, Volume: 46, Issue:11
Unsymmetrical DNA cross-linking agents: combination of the CBI and PBD pharmacophores.
AID232609Ratio of IC50 against A2780cisR (cisplatin resistant) to the IC50 of parent2001Journal of medicinal chemistry, Mar-01, Volume: 44, Issue:5
Design, synthesis, and evaluation of a novel pyrrolobenzodiazepine DNA-interactive agent with highly efficient cross-linking ability and potent cytotoxicity.
AID258717Cytotoxicity against LS174T human colon cell line after 1 hour of exposure2006Bioorganic & medicinal chemistry letters, Jan-15, Volume: 16, Issue:2
Synthesis and biological evaluation of novel pyrrolo[2,1-c][1,4]benzodiazepine prodrugs for use in antibody-directed enzyme prodrug therapy.
AID200302In vitro cellular toxicity against human ovarian carcinoma SKOV3 cell line after 4 hr of compound exposure2003Journal of medicinal chemistry, May-22, Volume: 46, Issue:11
Unsymmetrical DNA cross-linking agents: combination of the CBI and PBD pharmacophores.
AID228929Ratio of maximum tolerated dose of intravenous to intraperitoneal injection in mice2003Journal of medicinal chemistry, May-22, Volume: 46, Issue:11
Unsymmetrical DNA cross-linking agents: combination of the CBI and PBD pharmacophores.
AID52526In vitro cytotoxicity against human tumor COLO 205 cell line was measured as concentration to reduce [3H]thymidine uptake to 50% of that of the controls2003Journal of medicinal chemistry, May-22, Volume: 46, Issue:11
Unsymmetrical DNA cross-linking agents: combination of the CBI and PBD pharmacophores.
AID45977Thermal denaturation measured for calf thymus DNA after incubation at 37 degree at 0h.2002Journal of medicinal chemistry, Oct-10, Volume: 45, Issue:21
Design, synthesis, and evaluation of new noncross-linking pyrrolobenzodiazepine dimers with efficient DNA binding ability and potent antitumor activity.
AID1367556Antiproliferative activity against human OVCAR3 cells after 72 hrs by MTS assay2017Bioorganic & medicinal chemistry letters, 12-01, Volume: 27, Issue:23
Macrocyclic pyrrolobenzodiazepine dimers as antibody-drug conjugate payloads.
AID225423The concentration of compound required for 50% cross linking of plasmid pBR322 DNA was investigated using an assay involving linear double stranded DNA2001Journal of medicinal chemistry, Mar-01, Volume: 44, Issue:5
Design, synthesis, and evaluation of a novel pyrrolobenzodiazepine DNA-interactive agent with highly efficient cross-linking ability and potent cytotoxicity.
AID249982Increase in melting point temperature after 0h of incubation [1:5 ratio] as measurement of DNA binding affinity using calf thymus DNA2004Bioorganic & medicinal chemistry letters, Nov-15, Volume: 14, Issue:22
Synthesis of fluorinated analogues of SJG-136 and their DNA-binding potential.
AID122476Average time for WiDr tumor xenograft to reach a diameter of 17 mm following single intravenous injection at day 0 where tumor diameter was 8 mm in mice2003Journal of medicinal chemistry, May-22, Volume: 46, Issue:11
Unsymmetrical DNA cross-linking agents: combination of the CBI and PBD pharmacophores.
AID200303In vitro cytotoxicity against human tumor SKOV3 cell line was measured as concentration to reduce [3H]thymidine uptake to 50% of that of the controls2003Journal of medicinal chemistry, May-22, Volume: 46, Issue:11
Unsymmetrical DNA cross-linking agents: combination of the CBI and PBD pharmacophores.
AID215308In vitro cellular toxicity against chinese hamster UV4 cell line after 4 hr of compound exposure2003Journal of medicinal chemistry, May-22, Volume: 46, Issue:11
Unsymmetrical DNA cross-linking agents: combination of the CBI and PBD pharmacophores.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (7.69)18.2507
2000's11 (84.62)29.6817
2010's1 (7.69)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 23.36

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

MetricThis Compound (vs All)
Research Demand Index23.36 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index5.41 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (23.36)

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%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
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		3.1150
melphalan
Melphalan: An alkylating nitrogen mustard that is used as an antineoplastic in the form of the levo isomer - MELPHALAN, the racemic mixture - MERPHALAN, and the dextro isomer - MEDPHALAN; toxic to bone marrow, but little vesicant action; potential carcinogen.. melphalan : A phenylalanine derivative comprising L-phenylalanine having [bis(2-chloroethyl)amino group at the 4-position on the phenyl ring.		210L-phenylalanine derivative;
nitrogen mustard;
non-proteinogenic L-alpha-amino acid;
organochlorine compound		alkylating agent;
antineoplastic agent;
carcinogenic agent;
drug allergen;
immunosuppressive agent
anthramycin
[no description available]		2.0210
ConditionIndicatedRelationship StrengthStudiesTrials
Cancer of Colon
[description not available]		02.0310
Colonic Neoplasms
Tumors or cancer of the COLON.		02.0310