Page last updated: 2024-12-07
duocarmycin sa
Description
Research Excerpts
Clinical Trials
Roles
Classes
Pathways
Study Profile
Bioassays
Related Drugs
Related Conditions
Protein Interactions
Research Growth
Market Indicators
Description
duocarmycin SA: structure similar to CC-1065 and yatakemycin, composed of a pyrrolo-indole plus an indole; isolated from Streptomyces [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
Cross-References
ID Source | ID |
---|---|
PubMed CID | 115369 |
CHEMBL ID | 308086 |
SCHEMBL ID | 61916 |
MeSH ID | M0181506 |
Synonyms (14)
Synonym |
---|
duocarmycin sa |
antibiotic dc113 |
cyclopropa(c)pyrrolo(3,2-e)indole-6-carboxylic acid, 1,2,4,5,8,8a-hexahydro-4-oxo-2-((5,6,7-trimethoxy-1h-indol-2-yl)carbonyl)-, methyl ester, (7br)- |
(+)-duocarmycin sa |
CHEMBL308086 |
130288-24-3 |
SCHEMBL61916 |
DTXSID30926663 |
AKOS032946598 |
EX-A7932 |
methyl (1r,12s)-7-oxo-10-(5,6,7-trimethoxy-1h-indole-2-carbonyl)-5,10-diazatetracyclo[7.4.0.01,12.02,6]trideca-2(6),3,8-triene-4-carboxylate |
CS-0011400 |
HY-12456 |
duocarmycinsa |
Research Excerpts
Overview
Duocarmycin SA is a member of a growing class of interesting lead compounds for chemotherapy. It is distinguished by the manner in which they bind to and react with DNA substrates.
Excerpt | Reference | Relevance |
---|---|---|
"Duocarmycin SA is a member of a growing class of interesting lead compounds for chemotherapy, distinguished by the manner in which they bind to and react with DNA substrates. " | ( The structural basis for in situ activation of DNA alkylation by duocarmycin SA. Bifulco, G; Boger, DL; Case, DA; Chazin, WJ; Gomez-Paloma, L; Smith, JA, 2000) | 1.99 |
Effects
Excerpt | Reference | Relevance |
---|---|---|
"New duocarmycin SA derivatives have been synthesized and evaluated for in vitro anticellular activity against HeLa S3 cells, and in vivo antitumor activity against murine sarcoma 180 in mice. " | ( Studies on duocarmycin SA and its derivatives. Asai, A; Gomi, K; Kobayashi, E; Nagamura, S; Saito, H, 1997) | 1.24 |
Compound-Compound Interactions
Excerpt | Reference | Relevance |
---|---|---|
" Here, the lacZ-carrying vaccinia virus (VACV) strain GLV-1h68 was used in combination with a β-galactosidase-activatable prodrug derived from a seco-analog of the natural antibiotic duocarmycin SA." | ( Enhanced tumor therapy using vaccinia virus strain GLV-1h68 in combination with a β-galactosidase-activatable prodrug seco-analog of duocarmycin SA. Chen, N; Donat, U; Gentschev, I; Hess, M; Krewer, B; Seubert, CM; Stritzker, J; Sturm, JB; Szalay, AA; Tietze, LF; von Hof, JM, 2011) | 0.76 |
Dosage Studied
Excerpt | Relevance | Reference |
---|---|---|
" In vivo evaluation of the prodrug 6 showed that it exhibits extraordinary efficacy (T/C > 1500, L1210; 6/10 one year survivors), substantially exceeding that of the free drug, that its therapeutic window of activity is much larger, permitting a dosing ≥ 40-fold higher than the free drug, and yet that it displays a potency in vivo that approaches the free drug (within 3-fold)." | ( Efficacious cyclic N-acyl O-amino phenol duocarmycin prodrugs. Boger, DL; Brown, D; Duncan, KK; Parelkar, NK; Vielhauer, GA; Wolfe, AL, 2013) | 0.39 |
" This in turn permitted elevated dosing levels, leading to higher systemic exposure and a significantly improved response in tumor xenograft models." | ( A Novel Tumor-Activated Prodrug Strategy Targeting Ferrous Iron Is Effective in Multiple Preclinical Cancer Models. Fontaine, SD; Hann, B; Mattis, AN; Renslo, AR; Sambucetti, L; Shi, Y; Spangler, B; Wells, JA, 2016) | 0.43 |
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
Bioassays (35)
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID1395997 | Cytotoxicity against human U138MG cells assessed as cell survival at 0.5 nM after 72 hrs by trypan blue dye based assay | 2018 | Bioorganic & medicinal chemistry letters, 09-01, Volume: 28, Issue:16 | Duocarmycin SA, a potent antitumor antibiotic, sensitizes glioblastoma cells to proton radiation. |
AID537230 | Cytotoxicity against mouse L1210 cells | 2010 | Journal of medicinal chemistry, Nov-11, Volume: 53, Issue:21 | Design, synthesis, and evaluation of duocarmycin O-amino phenol prodrugs subject to tunable reductive activation. |
AID1396000 | Cytotoxicity against human U138MG cells assessed as dose enhancement ratio at 0.1 nM after 72 hrs in presence of 2 Gy dose of proton irradiation by trypan blue dye based assay | 2018 | Bioorganic & medicinal chemistry letters, 09-01, Volume: 28, Issue:16 | Duocarmycin SA, a potent antitumor antibiotic, sensitizes glioblastoma cells to proton radiation. |
AID512680 | Induction of thermal cleavage in protein free alpha satellite DNA 5'-GGAAAC-3' at 10 uM at 25 degC after 17 hrs by non-denaturating gel electrophoresis | 2006 | Nature chemical biology, Feb, Volume: 2, Issue:2 | Alkylation of duplex DNA in nucleosome core particles by duocarmycin SA and yatakemycin. |
AID1635392 | Induction of alkylation at Simian virus 40 150-bp DNA w794 after 24 hrs by PAGE and autoradiography method | 2016 | Bioorganic & medicinal chemistry, 10-15, Volume: 24, Issue:20 | Synthesis and evaluation of duocarmycin SA analogs incorporating the methyl 1,2,8,8a-tetrahydrocyclopropa[c]imidazolo[4,5-e]indol-4-one-6-carboxylate (CImI) alkylation subunit. |
AID1396011 | Anticlonogenic activity against human U138MG cells assessed as dose enhancement ratio pretreated for 2 hrs followed by 1 to 8 Gy dose of proton irradiation measured after 10 to 14 days by methylene blue staining based method | 2018 | Bioorganic & medicinal chemistry letters, 09-01, Volume: 28, Issue:16 | Duocarmycin SA, a potent antitumor antibiotic, sensitizes glioblastoma cells to proton radiation. |
AID431576 | Stability assessed as half life at pH 7 | 2009 | Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19 | Fundamental relationships between structure, reactivity, and biological activity for the duocarmycins and CC-1065. |
AID431574 | Cytotoxicity against mouse L1210 cells | 2009 | Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19 | Fundamental relationships between structure, reactivity, and biological activity for the duocarmycins and CC-1065. |
AID464157 | Alkylation of cell free 32p end labeled double stranded w794 DNA at 10 uM after 48 hrs by PAGE and autoradiography | 2010 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 20, Issue:6 | Synthesis and evaluation of duocarmycin SA analogs incorporating the methyl 1,2,8,8a-tetrahydrocyclopropa[c]oxazolo[2,3-e]indol-4-one-6-carboxylate (COI) alkylation subunit. |
AID1396009 | Anticlonogenic activity against human U138MG cells assessed as decrease in cell survival pretreated for 2 hrs followed by 1 to 8 Gy dose of proton irradiation measured after 10 to 14 days by methylene blue staining based method | 2018 | Bioorganic & medicinal chemistry letters, 09-01, Volume: 28, Issue:16 | Duocarmycin SA, a potent antitumor antibiotic, sensitizes glioblastoma cells to proton radiation. |
AID1395999 | Cytotoxicity against human U138MG cells assessed as decrease in cell viability after 72 hrs by trypan blue dye based assay | 2018 | Bioorganic & medicinal chemistry letters, 09-01, Volume: 28, Issue:16 | Duocarmycin SA, a potent antitumor antibiotic, sensitizes glioblastoma cells to proton radiation. |
AID512675 | Induction of thermal cleavage in alpha satellite DNA at 10 uM at 25 degC after 1 hr by non-denaturating gel electrophoresis | 2006 | Nature chemical biology, Feb, Volume: 2, Issue:2 | Alkylation of duplex DNA in nucleosome core particles by duocarmycin SA and yatakemycin. |
AID464156 | Cytotoxicity against mouse L1210 cells | 2010 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 20, Issue:6 | Synthesis and evaluation of duocarmycin SA analogs incorporating the methyl 1,2,8,8a-tetrahydrocyclopropa[c]oxazolo[2,3-e]indol-4-one-6-carboxylate (COI) alkylation subunit. |
AID1396010 | Anticlonogenic activity against human U138MG cells assessed as cell survival at 0.001 nM pretreated for 2 hrs followed by 1 to 8 Gy dose of proton irradiation measured after 10 to 14 days by methylene blue staining based method | 2018 | Bioorganic & medicinal chemistry letters, 09-01, Volume: 28, Issue:16 | Duocarmycin SA, a potent antitumor antibiotic, sensitizes glioblastoma cells to proton radiation. |
AID1635390 | Cytotoxicity against mouse L1210 cells assessed as cell growth inhibition | 2016 | Bioorganic & medicinal chemistry, 10-15, Volume: 24, Issue:20 | Synthesis and evaluation of duocarmycin SA analogs incorporating the methyl 1,2,8,8a-tetrahydrocyclopropa[c]imidazolo[4,5-e]indol-4-one-6-carboxylate (CImI) alkylation subunit. |
AID1396002 | Induction of apoptosis in human U138MG cells at 0.1 nM after 72 hrs by Annexin V staining based flow cytometry | 2018 | Bioorganic & medicinal chemistry letters, 09-01, Volume: 28, Issue:16 | Duocarmycin SA, a potent antitumor antibiotic, sensitizes glioblastoma cells to proton radiation. |
AID464158 | Alkylation of cell free 32p end labeled double stranded w794 DNA at 100 uM after 48 hrs by PAGE and autoradiography | 2010 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 20, Issue:6 | Synthesis and evaluation of duocarmycin SA analogs incorporating the methyl 1,2,8,8a-tetrahydrocyclopropa[c]oxazolo[2,3-e]indol-4-one-6-carboxylate (COI) alkylation subunit. |
AID98333 | In vitro cytotoxicity against L1210 cell line | 2000 | Bioorganic & medicinal chemistry letters, Mar-06, Volume: 10, Issue:5 | Bifunctional alkylating agents derived from duocarmycin SA: potent antitumor activity with altered sequence selectivity. |
AID1396003 | Induction of necrosis in human U138MG cells at 0.1 nM after 72 hrs by 7-AAD staining based flow cytometry | 2018 | Bioorganic & medicinal chemistry letters, 09-01, Volume: 28, Issue:16 | Duocarmycin SA, a potent antitumor antibiotic, sensitizes glioblastoma cells to proton radiation. |
AID1396005 | Induction of necrosis in human U138MG cells at 0.1 nM after 72 hrs in presence of 6 Gy dose of proton irradiation by 7-AAD staining based flow cytometry | 2018 | Bioorganic & medicinal chemistry letters, 09-01, Volume: 28, Issue:16 | Duocarmycin SA, a potent antitumor antibiotic, sensitizes glioblastoma cells to proton radiation. |
AID740033 | Cytotoxicity against mouse L1210 cells assessed as growth inhibition after 72 hrs by phosphatase assay | 2013 | Journal of medicinal chemistry, May-23, Volume: 56, Issue:10 | Efficacious cyclic N-acyl O-amino phenol duocarmycin prodrugs. |
AID470790 | Cytotoxicity against mouse L1210 cells | 2009 | Bioorganic & medicinal chemistry letters, Dec-15, Volume: 19, Issue:24 | Synthesis and evaluation of a thio analogue of duocarmycin SA. |
AID1396006 | Induction of apoptosis in human U138MG cells assessed as dose enhancement ratio at 0.1 nM after 72 hrs in presence of 2 Gy dose of proton irradiation by Annexin V staining based flow cytometry | 2018 | Bioorganic & medicinal chemistry letters, 09-01, Volume: 28, Issue:16 | Duocarmycin SA, a potent antitumor antibiotic, sensitizes glioblastoma cells to proton radiation. |
AID470791 | Induction of w794 DNA alkylation at 10 uM after 24 hrs by PAGE | 2009 | Bioorganic & medicinal chemistry letters, Dec-15, Volume: 19, Issue:24 | Synthesis and evaluation of a thio analogue of duocarmycin SA. |
AID1396004 | Induction of apoptosis in human U138MG cells at 0.1 nM after 72 hrs in presence of 6 Gy dose of proton irradiation by Annexin V staining based flow cytometry | 2018 | Bioorganic & medicinal chemistry letters, 09-01, Volume: 28, Issue:16 | Duocarmycin SA, a potent antitumor antibiotic, sensitizes glioblastoma cells to proton radiation. |
AID1395996 | Cytotoxicity against human U138MG cells assessed as cell survival at 0.1 nM after 72 hrs by trypan blue dye based assay | 2018 | Bioorganic & medicinal chemistry letters, 09-01, Volume: 28, Issue:16 | Duocarmycin SA, a potent antitumor antibiotic, sensitizes glioblastoma cells to proton radiation. |
AID1396007 | Induction of necrosis in human U138MG cells assessed as dose enhancement ratio at 0.1 nM after 72 hrs in presence of 2 Gy dose of proton irradiation by 7-AAD staining based flow cytometry | 2018 | Bioorganic & medicinal chemistry letters, 09-01, Volume: 28, Issue:16 | Duocarmycin SA, a potent antitumor antibiotic, sensitizes glioblastoma cells to proton radiation. |
AID512676 | Induction of thermal cleavage in alpha satellite DNA at 10 uM at 25 degC after 30 mins by non-denaturating gel electrophoresis | 2006 | Nature chemical biology, Feb, Volume: 2, Issue:2 | Alkylation of duplex DNA in nucleosome core particles by duocarmycin SA and yatakemycin. |
AID1395998 | Cytotoxicity against human U138MG cells assessed as cell survival at higher doses after 72 hrs by trypan blue dye based assay | 2018 | Bioorganic & medicinal chemistry letters, 09-01, Volume: 28, Issue:16 | Duocarmycin SA, a potent antitumor antibiotic, sensitizes glioblastoma cells to proton radiation. |
AID482107 | Cytotoxicity against mouse L1210 cells | 2010 | Bioorganic & medicinal chemistry letters, May-01, Volume: 20, Issue:9 | Synthesis and evaluation of a series of C5'-substituted duocarmycin SA analogs. |
AID431575 | Stability assessed as half life at pH 3 | 2009 | Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19 | Fundamental relationships between structure, reactivity, and biological activity for the duocarmycins and CC-1065. |
AID512677 | Binding affinity to alpha satellite DNA assessed as neucleosome reconstitution after 17 hrs at 25 degC by non-denaturating gel electrophoresis | 2006 | Nature chemical biology, Feb, Volume: 2, Issue:2 | Alkylation of duplex DNA in nucleosome core particles by duocarmycin SA and yatakemycin. |
AID1396001 | Cytotoxicity against human U138MG cells assessed as decrease in cell viability at 0.5 to 1 nM after 72 hrs in presence of 2 Gy dose of proton irradiation by trypan blue dye based assay | 2018 | Bioorganic & medicinal chemistry letters, 09-01, Volume: 28, Issue:16 | Duocarmycin SA, a potent antitumor antibiotic, sensitizes glioblastoma cells to proton radiation. |
AID690883 | Cytotoxicity against mouse L1210 cells | 2012 | Journal of medicinal chemistry, Jun-28, Volume: 55, Issue:12 | A novel, unusually efficacious duocarmycin carbamate prodrug that releases no residual byproduct. |
AID1396008 | Anticlonogenic activity against human U138MG cells assessed as decrease in cell survival after 14 days by methylene blue staining based method | 2018 | Bioorganic & medicinal chemistry letters, 09-01, Volume: 28, Issue:16 | Duocarmycin SA, a potent antitumor antibiotic, sensitizes glioblastoma cells to proton radiation. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Research
Studies (75)
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 0 (0.00) | 18.7374 |
1990's | 11 (14.67) | 18.2507 |
2000's | 44 (58.67) | 29.6817 |
2010's | 19 (25.33) | 24.3611 |
2020's | 1 (1.33) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Market Indicators
Research Demand Index: 19.61
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.
| This Compound (19.61) All Compounds (24.57) |
Study Types
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 5 (6.67%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 70 (93.33%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |