A cholic acid-peptide conjugate with antibacterial activity
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CAP 3

Item No. 27505

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-17-((R)-5-(benzyloxy)-5-oxopentan-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,7,12-triyl tris(2-((S)-2-amino-3-methylbutanamido)acetate)
CAS Number
2292123-03-4
Molecular Formula
C52H82N6O11
Formula Weight
967.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5mg/mLDMSO: 10mg/mLEthanol: 10mg/mLPBS (pH 7.2): 3mg/mL
SMILES
C[C@@]12[C@](CC[C@]2([H])[C@H](C)CCC(OCC3=CC=CC=C3)=O)([H])[C@]4([H])[C@H](OC(CNC([C@@H](N)C(C)C)=O)=O)C[C@]5([H])C[C@H](OC(CNC([C@@H](N)C(C)C)=O)=O)CC[C@]5(C)[C@@]4([H])C[C@@H]1OC(CNC([C@@H](N)C(C)C)=O)=O
InChi Code
InChI=1S/C52H82N6O11/c1-28(2)45(53)48(63)56-24-41(60)67-34-19-20-51(8)33(21-34)22-38(68-42(61)25-57-49(64)46(54)29(3)4)44-36-17-16-35(31(7)15-18-40(59)66-27-32-13-11-10-12-14-32)52(36,9)39(23-37(44)51)69-43(62)26-58-50(65)47(55)30(5)6/h10-14,28-31,33-39,44-47H,15-27,53-55H2,1-9H3,(H,56,63)(H,57,64)(H,58,65)/t31-,33+,34-,35-,36+,37+,38-,39+,44+,45+,46+,47+,51+,52-/m1/s1
InChi Key
XOMVHDKAGAIFOU-ZJADFBSCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    CAP 3 is a cholic acid-peptide conjugate (CAP) with antibacterial activity.1 It is active against the Gram-negative bacteria E. coli, K. pneumoniae, and A. baumanii (MIC99s = 8, 16, and 16 μM, respectively). CAP 3 increases the fluidity of model Gram-negative bacterial membranes and binds to LPS in vitro. It reduces the biomass and number of colony-forming units in E. coli biofilms in a concentration-dependent manner. CAP 3 inhibits E. coli biofilm formation on catheters implanted in mice infected with E. coli at the incision site when applied as a coating on the catheters. CAP 3 (40 mg/kg) also reduces bacterial load in E. coli-infected wounds in mice. It is cytotoxic to A459 cells (IC50 = 56.4 μM) and has hemolytic activity against human red blood cells with a 50% lysis (HC50) value of 48 μM.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yadav, K., Kumar, S., Mishra, D., et al. Deciphering the role of intramolecular networking in cholic acid-peptide conjugates on the lipopolysaccharide surface in combating Gram-negative bacterial infections. J. Med. Chem. 62(4), 1875-1886 (2019).