Page last updated: 2024-11-13

streptolydigin

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

streptolydigin: antibiotic isolated from culture filtrates of Streptomyces lydicus; active against gram-postive bacteria except micrococci; minor descriptor (75-87); on line & INDEX MEDICUS search ANTIBIOTICS (75-87) [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

streptolydigin : A monocarboxylic acid amide that is a broad-spectrum antibiotic produced by Streptomyces lydicus. [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]

Cross-References

ID SourceID
PubMed CID54708748
CHEMBL ID1236068
CHEBI ID45773
MeSH IDM0263415

Synonyms (27)

Synonym
CHEMBL1236068
chebi:45773 ,
free acid
antibiotic d-45
portamycin
streptolydigin
7229-50-7
nsc-3360
DB04785
afragilimycin a
1ZYR
nsc 3360
3-pyrroline-2-acetamide, 4-(6-(1,4-dimethylspiro(2,9-dioxabicyclo(3.3.1)non-6-ene-8,2'-oxiran)-3-yl)-4-methyl-2,4-heptadienoyl)-3-hydroxy-n,alpha-dimethyl-5-oxo-1-(tetrahydro-5-hydroxy-6-methyl-2h-pyran-2-yl)- (van)
6mon4029q8 ,
unii-6mon4029q8
2-pyrrolidineacetamide,4-[(2e,4e,6r)-6-[(1r,2'r,3r,4s,5r)-1,4-dimethylspiro[2,9-dioxabicyclo[3.3.1]non-6-ene-8,2'-oxiran]-3-yl]-1-hydroxy-4-methyl-2,4-heptadien-1-ylidene]-n,a-dimethyl-3,5-dioxo-1-[(2s,5s,6s)-tetrahydro-5-hydroxy-6-methyl-2h-pyran-2-yl]-,
streptolydigin [mi]
20611-71-6
KVTPRMVXYZKLIG-NCAOFHFGSA-N
(2s)-2-{(2s,4e)-4-{(2e,4e,6r)-6-[(1r,2r,5r,6s,7r)-1,6-dimethylspiro[8,9-dioxabicyclo[3.3.1]non-3-ene-2,2'-oxiran]-7-yl]-1-hydroxy-4-methylhepta-2,4-dien-1-ylidene}-1-[(2s,5s,6s)-5-hydroxy-6-methyltetrahydro-2h-pyran-2-yl]-3,5-dioxopyrrolidin-2-yl}-n-methy
2-pyrrolidineacetamide; portamycin
DTXSID20905083
Q5849706
HY-122337
CS-0083992
(2s)-2-[(2s,4e)-4-[(2e,4e,6r)-6-[(1r,3r,4s,5r,8r)-1,4-dimethylspiro[2,9-dioxabicyclo[3.3.1]non-6-ene-8,2'-oxirane]-3-yl]-1-hydroxy-4-methylhepta-2,4-dienylidene]-1-[(2s,5s,6s)-5-hydroxy-6-methyloxan-2-yl]-3,5-dioxopyrrolidin-2-yl]-n-methylpropanamide
AKOS040742653

Research Excerpts

Overview

Streptolydigin is a broadly effective antibiotic which inhibits RNA polymerase, similarly to rifampicin, a key drug in current TB chemotherapeutic regimens.

ExcerptReferenceRelevance
"Streptolydigin is a broadly effective antibiotic which inhibits RNA polymerase, similarly to rifampicin, a key drug in current TB chemotherapeutic regimens."( Mycobacterium tuberculosis is resistant to streptolydigin.
Niederweis, M; Rowland, JL; Speer, A, 2013
)
1.37
"Streptolydigin is a highly potent, broad-spectrum antibiotic produced by Streptomyces lydicus, which inhibits bacterial RNA polymerase. "( Synthesis of streptolydigin, a potent bacterial RNA polymerase inhibitor.
Kozmin, SA; Pronin, SV, 2010
)
2.17
"Streptolydigin is a tetramic acid antibiotic produced by Streptomyces lydicus NRRL 2433 and involving a hybrid polyketide synthase (PKS)-nonribosomal peptide synthetase (NRPS) system in its biosynthesis. "( Novel compounds produced by Streptomyces lydicus NRRL 2433 engineered mutants altered in the biosynthesis of streptolydigin.
Braña, AF; Carbajo, RJ; Gómez, C; Méndez, C; Olano, C; Palomino-Schätzlein, M; Pineda-Lucena, A; Salas, JA, 2012
)
2.03
"Streptolydigin (Stl) is a potent inhibitor of bacterial RNA polymerases (RNAPs). "( Structural basis of transcription inhibition by antibiotic streptolydigin.
Igarashi, N; Kashkina, E; Matsugaki, N; Nikiforov, V; Perederina, A; Savkina, M; Severinov, K; Tahirov, TH; Temiakov, D; Vassylyev, DG; Vassylyeva, MN; Wakatsuki, S; Zenkin, N; Zorov, S, 2005
)
2.01

Dosage Studied

ExcerptRelevanceReference
" The addition of GE23077 to plasmolyzed cells resulted in an immediate and specific inhibition of intracellular RNA biosynthesis, in a dose-response manner, strongly suggesting that cell penetration is the main obstacle for effective antimicrobial activity of the antibiotic."( Mode of action of the microbial metabolite GE23077, a novel potent and selective inhibitor of bacterial RNA polymerase.
Corti, E; Miele, A; Monti, F; Sarubbi, E; Selva, E, 2004
)
0.32
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
antimicrobial agentA substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
EC 2.7.7.6 (RNA polymerase) inhibitorAn EC 2.7.7.* (nucleotidyltransferase) inhibitor that interferes with the action of RNA polymerase (EC 2.7.7.6).
bacterial metaboliteAny prokaryotic metabolite produced during a metabolic reaction in bacteria.
[role 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]

Drug Classes (8)

ClassDescription
monocarboxylic acid amideA carboxamide derived from a monocarboxylic acid.
enolAlkenols; the term refers specifically to vinylic alcohols, which have the structure HOCR'=CR2. Enols are tautomeric with aldehydes (R' = H) or ketones (R' =/= H).
pyrrolidinone
N-glycosyl compoundA glycosyl compound arising formally from the elimination of water from a glycosidic hydroxy group and an H atom bound to a nitrogen atom, thus creating a C-N bond.
bridged compoundA polycyclic compound in which two rings have two or more atoms in common.
cyclic ketalA ketal in the molecule of which the ketal carbon and one or both oxygen atoms thereon are members of a ring.
spiro-epoxideAn oxaspiro compound in which a carbon atom of an epoxide ring is the only common member of two rings.
organic heterobicyclic compound
[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]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain C, DNA-directed RNA polymerase beta chainThermus thermophilusKi1.80001.80001.80001.8000AID977610
Chain D, DNA-directed RNA polymerase subunit beta' chainThermus thermophilusKi1.80001.80001.80001.8000AID977610
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (24)

Assay IDTitleYearJournalArticle
AID523634Antimicrobial activity against Streptomyces lydicus NRRL 2433 after 5 to 7 days2010Antimicrobial agents and chemotherapy, May, Volume: 54, Issue:5
Involvement of the beta subunit of RNA polymerase in resistance to streptolydigin and streptovaricin in the producer organisms Streptomyces lydicus and Streptomyces spectabilis.
AID523645Antimicrobial activity against transconjugant Streptomyces albus carrying pEM4T-Lbeta104 with RNA polymerase beta subunit F593Y mutant after 5 to 7 days2010Antimicrobial agents and chemotherapy, May, Volume: 54, Issue:5
Involvement of the beta subunit of RNA polymerase in resistance to streptolydigin and streptovaricin in the producer organisms Streptomyces lydicus and Streptomyces spectabilis.
AID523644Antimicrobial activity against transconjugant Streptomyces albus carrying pEM4T-Lbeta103 with RNA polymerase beta subunit L555V mutant after 5 to 7 days2010Antimicrobial agents and chemotherapy, May, Volume: 54, Issue:5
Involvement of the beta subunit of RNA polymerase in resistance to streptolydigin and streptovaricin in the producer organisms Streptomyces lydicus and Streptomyces spectabilis.
AID523638Antimicrobial activity against transconjugant Streptomyces albus carrying pEM4T-Lbeta after 5 to 7 days2010Antimicrobial agents and chemotherapy, May, Volume: 54, Issue:5
Involvement of the beta subunit of RNA polymerase in resistance to streptolydigin and streptovaricin in the producer organisms Streptomyces lydicus and Streptomyces spectabilis.
AID523650Antimicrobial activity against transconjugant Streptomyces albus carrying pEM4T-Abeta201 with RNA polymerase beta subunit F484L mutant after 5 to 7 days2010Antimicrobial agents and chemotherapy, May, Volume: 54, Issue:5
Involvement of the beta subunit of RNA polymerase in resistance to streptolydigin and streptovaricin in the producer organisms Streptomyces lydicus and Streptomyces spectabilis.
AID369451Antimicrobial activity against Staphylococcus epidermidis2007Antimicrobial agents and chemotherapy, Sep, Volume: 51, Issue:9
In vitro activities of different inhibitors of bacterial transcription against Staphylococcus epidermidis biofilm.
AID523635Antimicrobial activity against transconjugant Streptomyces albus J1074 after 5 to 7 days2010Antimicrobial agents and chemotherapy, May, Volume: 54, Issue:5
Involvement of the beta subunit of RNA polymerase in resistance to streptolydigin and streptovaricin in the producer organisms Streptomyces lydicus and Streptomyces spectabilis.
AID523648Antimicrobial activity against transconjugant Streptomyces albus carrying pEM4T-Lbeta107 with RNA polymerase beta subunit L485F/D486E mutant after 5 to 7 days2010Antimicrobial agents and chemotherapy, May, Volume: 54, Issue:5
Involvement of the beta subunit of RNA polymerase in resistance to streptolydigin and streptovaricin in the producer organisms Streptomyces lydicus and Streptomyces spectabilis.
AID523643Antimicrobial activity against transconjugant Streptomyces albus carrying pEM4T-Lbeta102 with RNA polymerase beta subunit D486E mutant after 5 to 7 days2010Antimicrobial agents and chemotherapy, May, Volume: 54, Issue:5
Involvement of the beta subunit of RNA polymerase in resistance to streptolydigin and streptovaricin in the producer organisms Streptomyces lydicus and Streptomyces spectabilis.
AID369459Inhibition of Staphylococcus epidermidis biofilm formation assessed as reduction of >2 log 10 bacterial count in biofilm after 24 hrs2007Antimicrobial agents and chemotherapy, Sep, Volume: 51, Issue:9
In vitro activities of different inhibitors of bacterial transcription against Staphylococcus epidermidis biofilm.
AID523651Antimicrobial activity against transconjugant Streptomyces albus carrying pEM4T-Abeta202 with RNA polymerase beta subunit E485D mutant after 5 to 7 days2010Antimicrobial agents and chemotherapy, May, Volume: 54, Issue:5
Involvement of the beta subunit of RNA polymerase in resistance to streptolydigin and streptovaricin in the producer organisms Streptomyces lydicus and Streptomyces spectabilis.
AID523640Antimicrobial activity against transconjugant Streptomyces albus carrying pEM4T-CALbeta after 5 to 7 days2010Antimicrobial agents and chemotherapy, May, Volume: 54, Issue:5
Involvement of the beta subunit of RNA polymerase in resistance to streptolydigin and streptovaricin in the producer organisms Streptomyces lydicus and Streptomyces spectabilis.
AID369452Ratio of MBC for Staphylococcus epidermidis to MIC for Staphylococcus epidermidis2007Antimicrobial agents and chemotherapy, Sep, Volume: 51, Issue:9
In vitro activities of different inhibitors of bacterial transcription against Staphylococcus epidermidis biofilm.
AID523636Antimicrobial activity against transconjugant Streptomyces albus carrying pEM4T after 5 to 7 days2010Antimicrobial agents and chemotherapy, May, Volume: 54, Issue:5
Involvement of the beta subunit of RNA polymerase in resistance to streptolydigin and streptovaricin in the producer organisms Streptomyces lydicus and Streptomyces spectabilis.
AID523637Antimicrobial activity against transconjugant Streptomyces albus carrying pEM4T-Abeta after 5 to 7 days2010Antimicrobial agents and chemotherapy, May, Volume: 54, Issue:5
Involvement of the beta subunit of RNA polymerase in resistance to streptolydigin and streptovaricin in the producer organisms Streptomyces lydicus and Streptomyces spectabilis.
AID523641Antimicrobial activity against transconjugant Streptomyces albus carrying pEM4T-Lbeta100 with RNA polymerase beta subunit T458N mutant after 5 to 7 days2010Antimicrobial agents and chemotherapy, May, Volume: 54, Issue:5
Involvement of the beta subunit of RNA polymerase in resistance to streptolydigin and streptovaricin in the producer organisms Streptomyces lydicus and Streptomyces spectabilis.
AID523639Antimicrobial activity against transconjugant Streptomyces albus carrying pEM4T-Lbeta' after 5 to 7 days2010Antimicrobial agents and chemotherapy, May, Volume: 54, Issue:5
Involvement of the beta subunit of RNA polymerase in resistance to streptolydigin and streptovaricin in the producer organisms Streptomyces lydicus and Streptomyces spectabilis.
AID523649Antimicrobial activity against transconjugant Streptomyces albus carrying pEM4T-Lbeta108 with RNA polymerase beta subunit F593Y/M594L mutant after 5 to 7 days2010Antimicrobial agents and chemotherapy, May, Volume: 54, Issue:5
Involvement of the beta subunit of RNA polymerase in resistance to streptolydigin and streptovaricin in the producer organisms Streptomyces lydicus and Streptomyces spectabilis.
AID369453Inhibition of Staphylococcus epidermidis RNA polymerase mediated transcription2007Antimicrobial agents and chemotherapy, Sep, Volume: 51, Issue:9
In vitro activities of different inhibitors of bacterial transcription against Staphylococcus epidermidis biofilm.
AID523652Antimicrobial activity against transconjugant Streptomyces albus carrying pEM4T-Abeta203 with RNA polymerase beta subunit F484L/E485D mutant after 5 to 7 days2010Antimicrobial agents and chemotherapy, May, Volume: 54, Issue:5
Involvement of the beta subunit of RNA polymerase in resistance to streptolydigin and streptovaricin in the producer organisms Streptomyces lydicus and Streptomyces spectabilis.
AID523646Antimicrobial activity against transconjugant Streptomyces albus carrying pEM4T-Lbeta105 with RNA polymerase beta subunit S624A mutant after 5 to 7 days2010Antimicrobial agents and chemotherapy, May, Volume: 54, Issue:5
Involvement of the beta subunit of RNA polymerase in resistance to streptolydigin and streptovaricin in the producer organisms Streptomyces lydicus and Streptomyces spectabilis.
AID523642Antimicrobial activity against transconjugant Streptomyces albus carrying pEM4T-Lbeta101 with RNA polymerase beta subunit L485F mutant after 5 to 7 days2010Antimicrobial agents and chemotherapy, May, Volume: 54, Issue:5
Involvement of the beta subunit of RNA polymerase in resistance to streptolydigin and streptovaricin in the producer organisms Streptomyces lydicus and Streptomyces spectabilis.
AID523647Antimicrobial activity against transconjugant Streptomyces albus carrying pEM4T-Lbeta106 with RNA polymerase beta subunit A636S mutant after 5 to 7 days2010Antimicrobial agents and chemotherapy, May, Volume: 54, Issue:5
Involvement of the beta subunit of RNA polymerase in resistance to streptolydigin and streptovaricin in the producer organisms Streptomyces lydicus and Streptomyces spectabilis.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB2005Cell, Aug-26, Volume: 122, Issue:4
Inhibition of bacterial RNA polymerase by streptolydigin: stabilization of a straight-bridge-helix active-center conformation.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (63)

TimeframeStudies, This Drug (%)All Drugs %
pre-199024 (38.10)18.7374
1990's7 (11.11)18.2507
2000's15 (23.81)29.6817
2010's17 (26.98)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: 25.10

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 Index25.10 (24.57)
Research Supply Index4.17 (2.92)
Research Growth Index4.60 (4.65)
Search Engine Demand Index29.35 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (25.10)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (4.69%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other61 (95.31%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]