7229-50-7

7229-50-7 structure

Name: Streptolydigin
Chemical Name: streptolydigin
CAS Number: 7229-50-7
Molecular Formula: C₃₂H₄₄N₂O₉
Molecular Weight: 600.70000
Catalog: Signaling Pathways Anti-infection Bacterial
Create Date: 2018-09-16 07:01:26
Modify Date: 2024-01-14 11:04:16
Streptolydigin (Portamycin) is a 3-acetyltetramic acid antibiotic and a potent bacterial RNA polymerase inhibitor with a Ki of 18 μM and a Kd of 15 μM. Streptolydigin inhibits RNA synthesis by binding to RNA polymerase and does not inhibit eukaryotic RNA polymerases[1][2][3]. Streptolydigin possess potent antibacterial activity, particularly against anaerobes and some Gram-positive aerobes[4].

Name	streptolydigin
Synonyms	Antibiotic D-45 portamycin Streptolydigin 2-Pyrrolidineacetamide, 4-[6-(1,4-dimethylspiro[2,9-dioxabicyclo[3.3.1]non-6-ene-8,2'-oxiran-3-yl)-1-hydroxy-4-methyl-2,4-heptadienylidene]-N,.α.-dimethyl-3,5-dioxo-1-(tetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl)-

Description	Streptolydigin (Portamycin) is a 3-acetyltetramic acid antibiotic and a potent bacterial RNA polymerase inhibitor with a Ki of 18 μM and a Kd of 15 μM. Streptolydigin inhibits RNA synthesis by binding to RNA polymerase and does not inhibit eukaryotic RNA polymerases[1][2][3]. Streptolydigin possess potent antibacterial activity, particularly against anaerobes and some Gram-positive aerobes[4].
Related Catalog	Research Areas >> Infection Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis Signaling Pathways >> Anti-infection >> Bacterial
Target	Ki: 18 μM (Bacterial RNA polymerase)[3] Kd: 15 μM (Bacterial RNA polymerase)[3]
In Vitro	The antibiotic Streptolydigin (Stl) is a derivative of 3-acetyltetramic acid. Binding of Streptolydigin to RNA polymerase strictly depends on a noncatalytic magnesium ion which is likely chelated by the aspartate of the bridge helix of the active center[1]. Streptolydigin inhibits T. thermophilus RNA polymerase with a Ki of 1.8 μM[3]. Streptolydigin (Stl) inhibits initiation, elongation, and pyrophosphorolysis by bacterial RNA polymerase. Streptolydigin interacts with three structural elements within RNAP: the Stl pocket, the bridge helix, and the trigger-loop region. The Streptolydigin streptolol moiety interacts with the Streptolydigin pocket and bridge helix, and the Streptolydigin tetramic-acid moiety interacts with the trigger-loop region[3].
References	[1]. Zorov S, et al. Antibiotic streptolydigin requires noncatalytic Mg2+ for binding to RNA polymerase. Antimicrob Agents Chemother. 2014;58(3):1420-4. [2]. Temiakov D, et al. Structural basis of transcription inhibition by antibiotic streptolydigin. Mol Cell. 2005 Sep 2;19(5):655-66. [3]. Tuske S, et al. Inhibition of bacterial RNA polymerase by streptolydigin: stabilization of a straight-bridge-helix active-center conformation. Cell. 2005 Aug 26;122(4):541-52. [4]. Rosen T, et al. Aromatic dienoyl tetramic acids. Novel antibacterial agents with activity against anaerobes and staphylococci. J Med Chem. 1989 May;32(5):1062-9.

Density	1.3 g/cm3
Boiling Point	826.6ºC at 760 mmHg
Molecular Formula	C₃₂H₄₄N₂O₉
Molecular Weight	600.70000
Flash Point	453.7ºC
Exact Mass	600.30500
PSA	147.16000
LogP	2.78890
Index of Refraction	1.598

CHEMICAL IDENTIFICATION

RTECS NUMBER :: WK4250000

CHEMICAL NAME :: Streptolydigin

CAS REGISTRY NUMBER :: 7229-50-7

LAST UPDATED :: 199403

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C32-H44-N2-O9

MOLECULAR WEIGHT :: 600.78

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 533 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Bird - chicken

DOSE/DURATION :: 10 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Bacteria - Bacillus subtilis

DOSE/DURATION :: 288 mg/L

REFERENCE :: FOMIAZ Folia Microbiologica (Prague). (Academia, Vodickova 40, 112 29 Prague 1, Czechoslavakia) V.4- 1959- Volume(issue)/page/year: 22,329,1977

Hazard Codes	Xi

2228309-32-6	2227778-11-0
1158522-08-7	940364-43-2
134104-43-1	131615-57-1
6906-52-1	930439-75-1
2287313-35-1	1018584-77-4