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P0025

Sigma-Aldrich

Platensimycin

≥90% (HPLC), from Streptomyces platensis

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About This Item

Empirical Formula (Hill Notation):
C24H27NO7
CAS Number:
835876-32-9
Molecular Weight:
441.47
UNSPSC Code:
51101500
PubChem Substance ID:
329819980

biological source

Streptomyces platensis

Assay

≥90% (HPLC)

form

solid

color

white to beige

solubility

DMSO: 1 mg/mL, clear, colorless

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

enzyme | inhibits

storage temp.

−20°C

SMILES string

O=C1C=C[C@]2(C[H])[C@H]3CC[C@@](O3)([H])C2C1CCC(CNC4=C(O)C=CC(C(O)=O)=C4O)=O

InChI

1S/C22H25NO7/c1-22-9-8-14(25)12(18(22)16-6-7-17(22)30-16)3-2-11(24)10-23-19-15(26)5-4-13(20(19)27)21(28)29/h4-5,8-9,12,16-18,23,26-27H,2-3,6-7,10H2,1H3,(H,28,29)/t12?,16-,17+,18?,22+/m0/s1

InChI key

IGBNLKVUOHQLTO-MBQNLBDGSA-N

Application

Platensimycin (PTM) is a broad-spectrum antibiotic produced by LStreptomyces platensis. Platensimycin is used to inhibit lipid biosynthesis. It is used in diabetes research and to study the potential treatment of metabolic disorders.

Biochem/physiol Actions

Demonstrates no cross-resistance to other antibiotic-resistant bacteria, including MRSA (methicillin-resistant Staphylococcus aureus).
Mode of action: Selectively inhibits lipid biosynthesis by targeting FabF/B within the fatty acid synthesis pathway.
Antimicrobial spectrum: Gram-positive bacteria.
Platensimycin selectively inhibits the elongation-condensing enzymes FabF/B of the fatty acid biosynthesis pathway in bacteria. PTM is a potent and highly selective inhibitor of mammalian fatty acid synthase. Platensimycin specifically inhibits fatty acid synthesis but not sterol synthesis in rat primary hepatocytes. It is thought that the thiol group of FabF Cys163 may be activated through the dipole moment of helix N-α-3 which lowers the pKa. It does not demonstrate cross-resistance to other antibiotic-resistant bacteria, including MRSA (methicillin-resistant Staphylococcus aureus). It is active against Gram-positive bacteria.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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International journal of molecular sciences, 16(8), 17909-17932 (2015-08-08)
Membrane permeability is a desired property in drug design, but there have been difficulties in quantifying the direct drug partitioning into native membranes. Platensimycin (PL) is a new promising antibiotic whose biosynthetic production is costly. Six dialkylamine analogs of PL
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