Compounds > dc 107
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dc 107

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 [MeSH]

Leinamycin : no description available [CHeBI]

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

Drug Classes (1)

ClassDescription
dithiolanes

Bioassays (31)

Assay IDTitleYearJournalArticle
AID331133Cytotoxicity against human HeLa S3 cells2008Bioorganic & medicinal chemistry letters, May-15, Volume: 18, Issue:10
ISSN: 1464-3405		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
ISSN: 1464-3391		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
ISSN: 1464-3391		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
ISSN: 1464-3405		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
ISSN: 1464-3391		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
ISSN: 0022-2623		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
ISSN: 1464-3405		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
ISSN: 0960-894X		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
ISSN: 1464-3405		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
ISSN: 1464-3405		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
ISSN: 1464-3391		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
ISSN: 1464-3405		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
ISSN: 0022-2623		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
ISSN: 1464-3391		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
ISSN: 1464-3391		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
ISSN: 0960-894X		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
ISSN: 1464-3391		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
ISSN: 1464-3391		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
ISSN: 1464-3405		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
ISSN: 1464-3391		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
ISSN: 1464-3391		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
ISSN: 1464-3391		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
ISSN: 1464-3391		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
ISSN: 1464-3405		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
ISSN: 1464-3405		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
ISSN: 1464-3405		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
ISSN: 0960-894X		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
ISSN: 0022-2623		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
ISSN: 1464-3391		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
ISSN: 0022-2623		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
ISSN: 1464-3405		Synthesis and evaluation of 8,4'-dideshydroxy-leinamycin revealing new insights into the structure-activity relationship of the anticancer natural product leinamycin.

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

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%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
lipoamide
0
dithiolanes;
monocarboxylic acid amide		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite		00low000000
thioctic acid
0
dithiolanes;
heterocyclic fatty acid;
thia fatty acid		fundamental metabolite;
geroprotector		00low000000
berlition
0
dithiolanes;
heterocyclic fatty acid;
lipoic acid;
thia fatty acid		cofactor;
nutraceutical;
prosthetic group		00low000000
nereistoxin
0
dithiolanesinsecticide;
toxin		00low000000
1,2-dithiolane-4-carboxylic acid
0
dithiolanecarboxylic acid;
dithiolanes;
sulfur-containing carboxylic acid		00low000000
isoprothiolane
0
dithiolanes;
isopropyl ester;
malonate ester		antifungal agrochemical;
environmental contaminant;
insecticide;
phospholipid biosynthesis inhibitor		00low000000
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
methoxyamine
1
organooxygen compound2012201212.0low000010
melphalan
1
L-phenylalanine derivative;
nitrogen mustard;
non-proteinogenic L-alpha-amino acid;
organochlorine compound		alkylating agent;
antineoplastic agent;
carcinogenic agent;
drug allergen;
immunosuppressive agent		2008200816.0low000100
bleomycin
1
bleomycinantineoplastic agent;
metabolite		2008200816.0low000100
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
benzoic acid
2
benzoic acidsalgal metabolite;
antimicrobial food preservative;
drug allergen;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
EC 3.1.1.3 (triacylglycerol lipase) inhibitor;
human xenobiotic metabolite;
plant metabolite		2007202010.5low000110
pyridoxal phosphate
1
methylpyridines;
monohydroxypyridine;
pyridinecarbaldehyde;
vitamin B6 phosphate		coenzyme;
cofactor;
EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite		201920195.0low000010
guanidine
1
carboxamidine;
guanidines;
one-carbon compound		2004200420.0low000100
methoxyamine
1
organooxygen compound2012201212.0low000010
netropsin
1
202020204.0low000010
alanine
1
alanine zwitterion;
alanine;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid		EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor;
fundamental metabolite		2007200717.0low000100
cyanides
1
pseudohalide anionEC 1.9.3.1 (cytochrome c oxidase) inhibitor2001200123.0low000100
dimethyl sulfate
1
alkyl sulfatealkylating agent;
immunosuppressive agent		2003200321.0low000100
pyrroles
1
pyrrole;
secondary amine		202020204.0low000010
thiophenes
1
mancude organic heteromonocyclic parent;
monocyclic heteroarene;
thiophenes;
volatile organic compound		non-polar solvent1996199628.0low001000
adamantane
1
adamantanes;
polycyclic alkane		201920195.0low000010
thiazoles
52
1,3-thiazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene		1989202217.1high02922172
mustard gas
1
ethyl sulfide;
organochlorine compound		alkylating agent;
carcinogenic agent;
vesicant		2003200321.0low000100
2-piperidone
1
delta-lactam;
piperidones		EC 1.2.1.88 (L-glutamate gamma-semialdehyde dehydrogenase) inhibitor201920195.0low000010
2-chloroethyl ethyl sulfide
1
2003200321.0low000100
dithiothreitol
1
1,4-dimercaptobutane-2,3-diol;
butanediols;
dithiol;
glycol;
thiol		chelator;
human metabolite;
reducing agent		1990199034.0low001000
fluorides
1
halide anion;
monoatomic fluorine		2007200717.0low000100
daunorubicin
1
aminoglycoside antibiotic;
anthracycline;
p-quinones;
tetracenequinones		antineoplastic agent;
bacterial metabolite		2011201113.0low000010
alkenes
1
2002200222.0low000100
allicin
1
botanical anti-fungal agent;
sulfoxide		antibacterial agent2007200717.0low000100
saframycin a
1
2011201113.0low000010
proline
1
amino acid zwitterion;
glutamine family amino acid;
L-alpha-amino acid;
proline;
proteinogenic amino acid		algal metabolite;
compatible osmolytes;
Escherichia coli metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite		202020204.0low000010
thiocysteine
1
amino acid zwitterion;
S-substituted L-cysteine		human metabolite;
mouse metabolite		202120213.0low000001
sodium perchlorate
1
inorganic sodium salt2003200321.0low000100
malonyl coenzyme a
2
malonyl-CoAsEC 2.3.1.21 (carnitine O-palmitoyltransferase) inhibitor;
Escherichia coli metabolite;
metabolite;
mouse metabolite		2003200619.5low000200
cystine
1
202120213.0low000001
mycosubtiline
1
201920195.0low000010
pactamycin
1
201920195.0low000010
sulfur
2
chalcogen;
nonmetal atom		macronutrient2000200720.5low001100
cysteine
4
cysteiniumfundamental metabolite2002202112.8low000211
platensimycin
1
aromatic amide;
cyclic ether;
cyclic ketone;
dihydroxybenzoic acid;
monocarboxylic acid amide;
polycyclic cage		antibacterial agent;
antimicrobial agent;
bacterial metabolite;
EC 2.3.1.85 (fatty acid synthase) inhibitor		201920195.0low000010
isomigrastatin
1
macrolide201920195.0low000010
oligonucleotides
2
2001200322.0low000200
platencin
1
aromatic amide;
cyclic ketone;
dihydroxybenzoic acid;
monocarboxylic acid amide;
polycyclic cage		antibacterial agent;
antimicrobial agent;
bacterial metabolite;
EC 2.3.1.85 (fatty acid synthase) inhibitor		201920195.0low000010
saxitoxin
1
alkaloid;
carbamate ester;
guanidines;
ketone hydrate;
paralytic shellfish toxin;
pyrrolopurine		cyanotoxin;
marine metabolite;
neurotoxin;
sodium channel blocker;
toxin		201920195.0low000010
guanine
3
2-aminopurines;
oxopurine;
purine nucleobase		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite		1997200522.3low001200
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
Benign Neoplasms0
1
2013201311.0medium000010
Cancer of Pancreas0
1
2004200420.0medium000100
Cancer of Prostate0
1
201520159.0medium000010
Leukemia P3880
1
2003200321.0medium000100
Neoplasms0
1
2013201311.0medium000010
Pancreatic Neoplasms0
1
2004200420.0medium000100
Prostatic Neoplasms0
1
201520159.0medium000010
Sarcoma 1800
2
1999200323.0high001100