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dc 107

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Description

leinamycin: a thiazole containing macrolide characterized by an unusual 1,3-dioxo-1,2-dithiolane moiety that is spiro fused to an 18 member macrolactam ring; isolated from Streptomyces; MF C22-H26-N2-O6-S3; possible DNA alkylator; the leinamycin biosynthetic gene cluster from Streptomyces atroolivaceus S-140 consists of two polyketide synthases genes [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID9849230
CHEMBL ID360089
CHEBI ID80015
MeSH IDM0164297

Synonyms (12)

Synonym
NSC645777 ,
streptomyces antibiotic dc-107
nsc-645777
leinamycin
120500-15-4
CHEMBL360089
chebi:80015 ,
dc-107
Q25323729
dc107
(2r,4'r,6r,9e,11r,13e,15z)-4',11-dihydroxy-2,4',9-trimethyl-1'-oxospiro[19-thia-3,20-diazabicyclo[15.2.1]icosa-1(20),9,13,15,17-pentaene-6,5'-dithiolane]-3',4,12-trione
gtpl11041
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
dithiolanes
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (31)

Assay IDTitleYearJournalArticle
AID331133Cytotoxicity against human HeLa S3 cells2008Bioorganic & medicinal chemistry letters, May-15, Volume: 18, Issue:10
Possible chemical mechanisms underlying the antitumor activity of S-deoxyleinamycin.
AID716724Cytotoxicity against chinese hamster kU86-mutant Xrs-5 cells assessed as cell survival by clonogenic survival assay2012Bioorganic & medicinal chemistry, Jul-15, Volume: 20, Issue:14
DNA cleavage induced by antitumor antibiotic leinamycin and its biological consequences.
AID716720Ratio for chinese hamster AA8 cells to chinese hamster BER-mutant EM9 cells2012Bioorganic & medicinal chemistry, Jul-15, Volume: 20, Issue:14
DNA cleavage induced by antitumor antibiotic leinamycin and its biological consequences.
AID1249584Cytotoxicity against human A375 cells after 4 days by MTT assay2015Bioorganic & medicinal chemistry letters, Nov-01, Volume: 25, Issue:21
Synthesis and evaluation of 8,4'-dideshydroxy-leinamycin revealing new insights into the structure-activity relationship of the anticancer natural product leinamycin.
AID712885Induction of DNA cleavage in 32P-labeled oligomer duplex Sp25 DNA at 2 ug/ml to 100 ug/ml after 24 hrs by PAGE analysis without hot piperidine treatment2012Bioorganic & medicinal chemistry, Jul-15, Volume: 20, Issue:14
DNA cleavage induced by antitumor antibiotic leinamycin and its biological consequences.
AID121812In vivo antitumor activity against sarcoma 180 infected mice was determined as treated versus control of tumor volume1999Journal of medicinal chemistry, Apr-22, Volume: 42, Issue:8
Synthesis and antitumor activity of novel thioester derivatives of leinamycin.
AID1249587Cytotoxicity against human T47D cells after 4 days by MTT assay2015Bioorganic & medicinal chemistry letters, Nov-01, Volume: 25, Issue:21
Synthesis and evaluation of 8,4'-dideshydroxy-leinamycin revealing new insights into the structure-activity relationship of the anticancer natural product leinamycin.
AID99264In vivo antitumor activity of compound was tested as maximal increase in life span (ILSmax) against lymphocytic leukemia P388 in mice1998Bioorganic & medicinal chemistry letters, Apr-21, Volume: 8, Issue:8
Synthesis and antitumor activity of leinamycin derivatives: modifications of C-8 hydroxy and C-9 keto groups.
AID1249589Cytotoxicity against human MDA-MB-231 cells after 4 days by MTT assay2015Bioorganic & medicinal chemistry letters, Nov-01, Volume: 25, Issue:21
Synthesis and evaluation of 8,4'-dideshydroxy-leinamycin revealing new insights into the structure-activity relationship of the anticancer natural product leinamycin.
AID671221Half life of the compound at 100 uM in HEPES buffer (250 mM, pH 7.0) at 24 degC containing no organic solvent2012Bioorganic & medicinal chemistry letters, Jun-01, Volume: 22, Issue:11
The macrocycle of leinamycin imparts hydrolytic stability to the thiol-sensing 1,2-dithiolan-3-one 1-oxide unit of the natural product.
AID712889Cytotoxicity against chinese hamster NER-mutant UV5 cells assessed as cell survival by clonogenic survival assay2012Bioorganic & medicinal chemistry, Jul-15, Volume: 20, Issue:14
DNA cleavage induced by antitumor antibiotic leinamycin and its biological consequences.
AID1249588Cytotoxicity against human SKBR cells after 4 days by MTT assay2015Bioorganic & medicinal chemistry letters, Nov-01, Volume: 25, Issue:21
Synthesis and evaluation of 8,4'-dideshydroxy-leinamycin revealing new insights into the structure-activity relationship of the anticancer natural product leinamycin.
AID26136Half-life determined by HPLC (330 nM)1999Journal of medicinal chemistry, Apr-22, Volume: 42, Issue:8
Synthesis and antitumor activity of novel thioester derivatives of leinamycin.
AID712888Induction of DNA cleavage in 32P-labeled oligomer duplex Sp25 DNA after 8 hrs by PAGE analysis with hot piperidine treatment2012Bioorganic & medicinal chemistry, Jul-15, Volume: 20, Issue:14
DNA cleavage induced by antitumor antibiotic leinamycin and its biological consequences.
AID716726Cytotoxicity against chinese hamster NER-mutant UV41 cells assessed as cell survival by clonogenic survival assay2012Bioorganic & medicinal chemistry, Jul-15, Volume: 20, Issue:14
DNA cleavage induced by antitumor antibiotic leinamycin and its biological consequences.
AID87749In vitro antiproliferative activity against human uterine carcinoma HeLa S3 cells.1998Bioorganic & medicinal chemistry letters, Apr-21, Volume: 8, Issue:8
Synthesis and antitumor activity of leinamycin derivatives: modifications of C-8 hydroxy and C-9 keto groups.
AID712886Induction of DNA cleavage in 32P-labeled oligomer duplex Sp25 DNA at 2 ug/ml to 100 ug/ml after 24 hrs by PAGE analysis followed by hot piperidine treatment2012Bioorganic & medicinal chemistry, Jul-15, Volume: 20, Issue:14
DNA cleavage induced by antitumor antibiotic leinamycin and its biological consequences.
AID716730Cytotoxicity against human MiaPaCa cells by MTT assay2012Bioorganic & medicinal chemistry, Jul-15, Volume: 20, Issue:14
DNA cleavage induced by antitumor antibiotic leinamycin and its biological consequences.
AID669388Half life of the compound at 70 uM in MOPS aqueous buffer (250 mM, pH 7.0) containing MeCN (25% v/v) at 24 degC by HPLC analysis2012Bioorganic & medicinal chemistry letters, Jun-01, Volume: 22, Issue:11
The macrocycle of leinamycin imparts hydrolytic stability to the thiol-sensing 1,2-dithiolan-3-one 1-oxide unit of the natural product.
AID716727Cytotoxicity against chinese hamster AA8 cells assessed as cell survival by clonogenic survival assay2012Bioorganic & medicinal chemistry, Jul-15, Volume: 20, Issue:14
DNA cleavage induced by antitumor antibiotic leinamycin and its biological consequences.
AID716723Cytotoxicity against chinese hamster BER-mutant EM9 cells assessed as cell survival by clonogenic survival assay2012Bioorganic & medicinal chemistry, Jul-15, Volume: 20, Issue:14
DNA cleavage induced by antitumor antibiotic leinamycin and its biological consequences.
AID716728Cytotoxicity against human MiaPaCa cells assessed as potentiation of methoxyamine-mediated cytotoxicity by MTT assay2012Bioorganic & medicinal chemistry, Jul-15, Volume: 20, Issue:14
DNA cleavage induced by antitumor antibiotic leinamycin and its biological consequences.
AID716725Cytotoxicity against chinese hamster NER-mutant UV135 cells assessed as cell survival by clonogenic survival assay2012Bioorganic & medicinal chemistry, Jul-15, Volume: 20, Issue:14
DNA cleavage induced by antitumor antibiotic leinamycin and its biological consequences.
AID669389Half life of the compound at 70 uM in MOPS aqueous buffer (300 mM, pH 7.0) containing MeCN (25% v/v) at 24 degC in presence of 700 uM GSH by HPLC analysis2012Bioorganic & medicinal chemistry letters, Jun-01, Volume: 22, Issue:11
The macrocycle of leinamycin imparts hydrolytic stability to the thiol-sensing 1,2-dithiolan-3-one 1-oxide unit of the natural product.
AID671222Half life of the compound in sodium phosphate buffer (10 mM, pH 7.0) at 37 degC containing methanol (10% v/v)2012Bioorganic & medicinal chemistry letters, Jun-01, Volume: 22, Issue:11
The macrocycle of leinamycin imparts hydrolytic stability to the thiol-sensing 1,2-dithiolan-3-one 1-oxide unit of the natural product.
AID1249586Cytotoxicity against human MCF7 cells after 4 days by MTT assay2015Bioorganic & medicinal chemistry letters, Nov-01, Volume: 25, Issue:21
Synthesis and evaluation of 8,4'-dideshydroxy-leinamycin revealing new insights into the structure-activity relationship of the anticancer natural product leinamycin.
AID99266Compound was tested in vivo for antitumor activity against lymphocytic leukemia P388 in mice1998Bioorganic & medicinal chemistry letters, Apr-21, Volume: 8, Issue:8
Synthesis and antitumor activity of leinamycin derivatives: modifications of C-8 hydroxy and C-9 keto groups.
AID87753In vitro antiproliferative activity against HeLa S3 cells1999Journal of medicinal chemistry, Apr-22, Volume: 42, Issue:8
Synthesis and antitumor activity of novel thioester derivatives of leinamycin.
AID712887Induction of DNA cleavage in 32P-labeled oligomer duplex Sp25 DNA up to 24 hrs by PAGE analysis without hot piperidine treatment2012Bioorganic & medicinal chemistry, Jul-15, Volume: 20, Issue:14
DNA cleavage induced by antitumor antibiotic leinamycin and its biological consequences.
AID119956Optimal dose for in vivo antitumor activity against sarcoma 180 infected mice1999Journal of medicinal chemistry, Apr-22, Volume: 42, Issue:8
Synthesis and antitumor activity of novel thioester derivatives of leinamycin.
AID1249585Cytotoxicity against human Raji cells after 4 days by MTT assay2015Bioorganic & medicinal chemistry letters, Nov-01, Volume: 25, Issue:21
Synthesis and evaluation of 8,4'-dideshydroxy-leinamycin revealing new insights into the structure-activity relationship of the anticancer natural product leinamycin.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (53)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (3.77)18.7374
1990's5 (9.43)18.2507
2000's25 (47.17)29.6817
2010's17 (32.08)24.3611
2020's4 (7.55)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%
Reviews5 (9.43%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other48 (90.57%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]