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{{Short description|Chemical compound}}
{{drugbox
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 470471049
| IUPAC_name = 2-[4-[6-(1,6-dimethylspiro[8,9-dioxabicyclo[3.3.1]non-3-ene-2,2'-oxirane]-7
| IUPAC_name = 2-[4-[6-(1,6-dimethylspiro[8,9-dioxabicyclo[3.3.1]non-3-ene-2,2'-oxirane]-7
-yl)-4-methylhepta-2,4-dienoyl]-5-hydroxy-1-(5-hydroxy-6-methyloxan-2-yl)-3
-oxo-2H-pyrrol-2-yl]-N-methylpropanamide
| image = Streptolydigin.png
| image = Streptolydigin.png

<!--Clinical data-->
| tradename =
⚫
| pregnancy_category =
⚫
| legal_status =
⚫
| routes_of_administration =

<!--Pharmacokinetic data-->
⚫
| bioavailability =
⚫
| protein_bound =
⚫
| metabolism =
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| elimination_half-life =

<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 7229-50-7
| CAS_number = 7229-50-7
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
| ATC_prefix =
| UNII = 6MON4029Q8
⚫
| ATC_prefix = none
| ATC_suffix =
| ATC_suffix =
| ATC_supplemental =
| ATC_supplemental =
| PubChem = 220508
| PubChem = 220508
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| DrugBank = DB04785
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 16736035
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1236068
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 45773

<!--Chemical data-->
| C=32 | H=44 | N=2 | O=9
| C=32 | H=44 | N=2 | O=9
| smiles = CNC(=O)C(C)C2C(=O)/C(C(=O)N2C1CCC(O)C(C)O1)=C(\O)/C=C/C(/C)=C/C(C)C5OC4(C)OC(\C=C/C34CO3)C5C
| molecular_weight = 600.708 g/mol
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫
| bioavailability =
| StdInChI = 1S/C32H44N2O9/c1-16(14-17(2)28-18(3)23-12-13-32(15-40-32)31(6,42-23)43-28)8-9-22(36)25-27(37)26(19(4)29(38)33-7)34(30(25)39)24-11-10-21(35)20(5)41-24/h8-9,12-14,17-21,23-24,26,28,35-36H,10-11,15H2,1-7H3,(H,33,38)/b9-8+,16-14+,25-22+
⚫
| protein_bound =
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫
| metabolism =
| StdInChIKey = KVTPRMVXYZKLIG-NCFIBNQNSA-N
⚫
| elimination_half-life =
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| pregnancy_category =
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| legal_status =
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| routes_of_administration =
}}
}}


'''Streptolydigin''' (Stl) is an [[antibiotic]] that works by inhibiting [[nucleic acid]] chain elongation by binding to [[RNA polymerase]], thus inhibiting [[RNA]] synthesis inside a [[cell (biology)|cell]].<ref>{{cite journal | vauthors = Tuske S, Sarafianos SG, Wang X, Hudson B, Sineva E, Mukhopadhyay J, Birktoft JJ, Leroy O, Ismail S, Clark AD, Dharia C, Napoli A, Laptenko O, Lee J, Borukhov S, Ebright RH, Arnold E | display-authors = 6 | title = Inhibition of bacterial RNA polymerase by streptolydigin: stabilization of a straight-bridge-helix active-center conformation | journal = Cell | volume = 122 | issue = 4 | pages = 541–52 | date = August 2005 | pmid = 16122422 | pmc = 2754413 | doi = 10.1016/j.cell.2005.07.017 }}</ref><ref>{{cite journal | vauthors = Temiakov D, Zenkin N, Vassylyeva MN, Perederina A, Tahirov TH, Kashkina E, Savkina M, Zorov S, Nikiforov V, Igarashi N, Matsugaki N, Wakatsuki S, Severinov K, Vassylyev DG | display-authors = 6 | title = Structural basis of transcription inhibition by antibiotic streptolydigin | journal = Molecular Cell | volume = 19 | issue = 5 | pages = 655–66 | date = September 2005 | pmid = 16167380 | doi = 10.1016/j.molcel.2005.07.020 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Vassylyev DG, Vassylyeva MN, Zhang J, Palangat M, Artsimovitch I, Landick R | s2cid = 4320480 | title = Structural basis for substrate loading in bacterial RNA polymerase | journal = Nature | volume = 448 | issue = 7150 | pages = 163–8 | date = July 2007 | pmid = 17581591 | doi = 10.1038/nature05931 | arxiv = 0707.3064 | bibcode = 2007Natur.448..163V }}</ref> Streptolydigin inhibits bacterial RNA polymerase, but not eukaryotic RNA polymerase.<ref>{{cite journal | vauthors = Tuske S, Sarafianos SG, Wang X, Hudson B, Sineva E, Mukhopadhyay J, Birktoft JJ, Leroy O, Ismail S, Clark AD, Dharia C, Napoli A, Laptenko O, Lee J, Borukhov S, Ebright RH, Arnold E | display-authors = 6 | title = Inhibition of bacterial RNA polymerase by streptolydigin: stabilization of a straight-bridge-helix active-center conformation | journal = Cell | volume = 122 | issue = 4 | pages = 541–52 | date = August 2005 | pmid = 16122422 | pmc = 2754413 | doi = 10.1016/j.cell.2005.07.017 }}</ref> It has antibacterial activity against a number of [[Gram positive]] [[bacteria]].{{cn|date=January 2023}}
'''Streptolydigin''' is an [[antibiotic]] which works by blocking [[nucleic acid]] chain elongation by binding to the [[polymerase]], thus stopping [[RNA]] polymerase activity inside a [[cell (biology)|cell]]. Specifically, it inhibits the assembly of the [[RNA polymerase II]] transcription complex and [[DNA polymerase III]] transcription. It is active against a number of [[gram positive]] [[bacteria]].


== References ==

{{antibiotic-stub}}
{{Reflist}}


[[Category:Antibiotics]]
[[Category:Antibiotics]]
[[Category:Spiro compounds]]
[[Category:Pyrrolidones]]
[[Category:Propionamides]]

{{antibiotic-stub}}

Latest revision as of 20:47, 29 January 2023

Streptolydigin
Clinical data
ATC code
  • none
Identifiers
  • 2-[4-[6-(1,6-dimethylspiro[8,9-dioxabicyclo[3.3.1]non-3-ene-2,2'-oxirane]-7
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC32H44N2O9
Molar mass600.709 g·mol−1
3D model (JSmol)
  • CNC(=O)C(C)C2C(=O)/C(C(=O)N2C1CCC(O)C(C)O1)=C(\O)/C=C/C(/C)=C/C(C)C5OC4(C)OC(\C=C/C34CO3)C5C
  • InChI=1S/C32H44N2O9/c1-16(14-17(2)28-18(3)23-12-13-32(15-40-32)31(6,42-23)43-28)8-9-22(36)25-27(37)26(19(4)29(38)33-7)34(30(25)39)24-11-10-21(35)20(5)41-24/h8-9,12-14,17-21,23-24,26,28,35-36H,10-11,15H2,1-7H3,(H,33,38)/b9-8+,16-14+,25-22+ checkY
  • Key:KVTPRMVXYZKLIG-NCFIBNQNSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Streptolydigin (Stl) is an antibiotic that works by inhibiting nucleic acid chain elongation by binding to RNA polymerase, thus inhibiting RNA synthesis inside a cell.[1][2][3] Streptolydigin inhibits bacterial RNA polymerase, but not eukaryotic RNA polymerase.[4] It has antibacterial activity against a number of Gram positive bacteria.[citation needed]

References[edit]

  1. ^ Tuske S, Sarafianos SG, Wang X, Hudson B, Sineva E, Mukhopadhyay J, et al. (August 2005). "Inhibition of bacterial RNA polymerase by streptolydigin: stabilization of a straight-bridge-helix active-center conformation". Cell. 122 (4): 541–52. doi:10.1016/j.cell.2005.07.017. PMC 2754413. PMID 16122422.
  2. ^ Temiakov D, Zenkin N, Vassylyeva MN, Perederina A, Tahirov TH, Kashkina E, et al. (September 2005). "Structural basis of transcription inhibition by antibiotic streptolydigin". Molecular Cell. 19 (5): 655–66. doi:10.1016/j.molcel.2005.07.020. PMID 16167380.
  3. ^ Vassylyev DG, Vassylyeva MN, Zhang J, Palangat M, Artsimovitch I, Landick R (July 2007). "Structural basis for substrate loading in bacterial RNA polymerase". Nature. 448 (7150): 163–8. arXiv:0707.3064. Bibcode:2007Natur.448..163V. doi:10.1038/nature05931. PMID 17581591. S2CID 4320480.
  4. ^ Tuske S, Sarafianos SG, Wang X, Hudson B, Sineva E, Mukhopadhyay J, et al. (August 2005). "Inhibition of bacterial RNA polymerase by streptolydigin: stabilization of a straight-bridge-helix active-center conformation". Cell. 122 (4): 541–52. doi:10.1016/j.cell.2005.07.017. PMC 2754413. PMID 16122422.
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