A channel-forming ionophore
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Gramicidin A

Item No. 26384

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(R)-2-((2S,5R,8S,11R,14S,17R,20S,26S)-2-((1H-indol-3-yl)methyl)-17-isobutyl-5,8,11,26-tetraisopropyl-14,20-dimethyl-4,7,10,13,16,19,22,27,28-nonaoxo-3,6,9,12,15,18,21,24,25-nonaazaoctacosanamido)-N-((5S,8R,11S,14R,17S)-5,11-bis((1H-indol-3-yl)methyl)-1-hydroxy-18-(1H-indol-3-yl)-8,14-diisobutyl-4,7,10,13,16-pentaoxo-3,6,9,12,15-pentaazaoctadecan-17-yl)-4-methylpentanamide
CAS Number
11029-61-1
Molecular Formula
C99H140N20O17
Formula Weight
1882.3
Purity
≥90%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: solubleEthanol: solubleWater: slightly soluble
λmax
223 nm
SMILES
[H]C(N[C@H](C(NCC(N[C@@H](C)C(N[C@@H](C(N[C@@H](C)C(N[C@@H](C(N[C@H](C(N[C@@H](C(N[C@@H](CC1=CNC2=C1C=CC=C2)C(N[C@@H](C(N[C@@H](CC3=CNC4=C3C=CC=C4)C(N[C@@H](C(N[C@@H](CC5=CNC6=C5C=CC=C6)C(N[C@@H](C(N[C@@H](CC7=CNC8=C7C=CC=C8)C(NCCO)=O)=O)CC(C)C)=O)=O)CC(C)C)=O)=O)CC(C)C)=O)=O)C(C)C)=O)C(C)C)=O)C(C)C)=O)=O)CC(C)C)=O)=O)=O)C(C)C)=O
InChi Code
InChI=1S/C99H140N20O17/c1-51(2)37-73(109-86(123)59(17)107-81(122)49-105-96(133)82(55(9)10)106-50-121)89(126)108-60(18)87(124)117-84(57(13)14)98(135)119-85(58(15)16)99(136)118-83(56(11)12)97(134)116-80(44-64-48-104-72-34-26-22-30-68(64)72)95(132)112-76(40-54(7)8)92(129)115-79(43-63-47-103-71-33-25-21-29-67(63)71)94(131)111-75(39-53(5)6)91(128)114-78(42-62-46-102-70-32-24-20-28-66(62)70)93(130)110-74(38-52(3)4)90(127)113-77(88(125)100-35-36-120)41-61-45-101-69-31-23-19-27-65(61)69/h19-34,45-48,50-60,73-80,82-85,101-104,120H,35-44,49H2,1-18H3,(H,100,125)(H,105,133)(H,106,121)(H,107,122)(H,108,126)(H,109,123)(H,110,130)(H,111,131)(H,112,132)(H,113,127)(H,114,128)(H,115,129)(H,116,134)(H,117,124)(H,118,136)(H,119,135)/t59-,60-,73+,74+,75+,76+,77-,78-,79-,80-,82-,83+,84+,85-/m0/s1
InChi Key
ZWCXYZRRTRDGQE-LUPIJMBPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Gramicidin A is a peptide component of gramicidin, an antibiotic mixture originally isolated from B. brevis.1 Gramicidin A is a highly hydrophobic channel-forming ionophore that forms channels in model membranes that are permeable to monovalent cations. It induces degradation of hypoxia inducible factor 1 α (HIF-1α) in HEK293 cells and reduces growth in a human renal cell carcinoma mouse xenograft model when administered at a dose of 0.22 mg/kg three times per week.2 Gramicidin A has commonly been used to study channel structure and function.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kelkar, D.A., and Chattopadhyay, A. The gramicidin ion channel: A model membrane protein. Biochim. Biophys. Acta 1768(9), 2011-2025 (2007).

    2. David, J.M., Owens, T.A., Inge, L.J., et al. Gramicidin A blocks tumor growth and angiogenesis through inhibition of hypoxia-inducible factor in renal cell carcinoma. Mol. Cancer Ther. 13(4), 788-799 (2014).