WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H465243
CAS#: 63988-20-5
Description: Tetramyristoylcardiolipin is a is a cationic lipid for RNA and vaccine delivery.
Hodoodo Cat#: H465243
Name: Tetramyristoylcardiolipin ammonium
CAS#: 63988-20-5
Chemical Formula: C65H132N2O17P2
Exact Mass: 1,274.90
Molecular Weight: 1,275.716
Elemental Analysis: C, 61.20; H, 10.43; N, 2.20; O, 21.32; P, 4.86
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Synonym: Tetramyristoylcardiolipin; Tetramyristoylcardiolipin ammonium; Tetramyristoylcardiolipin ammonium salt
IUPAC/Chemical Name: ammonium bis((R)-2,3-bis(tetradecanoyloxy)propyl) (2-hydroxypropane-1,3-diyl) bis(phosphate)
InChi Key: WUHLCMIVLGWFSP-MWZRJEOUSA-N
InChi Code: InChI=1S/C65H126O17P2.2H3N/c1-5-9-13-17-21-25-29-33-37-41-45-49-62(67)75-55-60(81-64(69)51-47-43-39-35-31-27-23-19-15-11-7-3)57-79-83(71,72)77-53-59(66)54-78-84(73,74)80-58-61(82-65(70)52-48-44-40-36-32-28-24-20-16-12-8-4)56-76-63(68)50-46-42-38-34-30-26-22-18-14-10-6-2;;/h59-61,66H,5-58H2,1-4H3,(H,71,72)(H,73,74);2*1H3/t60-,61-;;/m1../s1
SMILES Code: [O-]P(OCC(O)COP(OC[C@H](OC(CCCCCCCCCCCCC)=O)COC(CCCCCCCCCCCCC)=O)([O-])=O)(OC[C@H](OC(CCCCCCCCCCCCC)=O)COC(CCCCCCCCCCCCC)=O)=O.[NH4+].[NH4+]
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: To be determined
Shelf Life: >2 years if stored properly
Drug Formulation: To be determined
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 1,275.72 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Fox CA, Ellison P, Ikon N, Ryan RO. Calcium-induced transformation of cardiolipin nanodisks. Biochim Biophys Acta Biomembr. 2019 May 1;1861(5):1030-1036. doi: 10.1016/j.bbamem.2019.03.005. Epub 2019 Mar 13. PMID: 30876942; PMCID: PMC6436997.
2: Efimova SS, Medvedev RY, Schagin LV, Ostroumova OS. NCREASING OF THE FLUIDITY OF MODEL LIPID MEMBRANES UNDER THE INFLUENCE OF LOCAL ANESTHETICS. Tsitologiia. 2016;58(5):378-84. English, Russian. PMID: 30188636.
3: Benesch MG, Lewis RN, McElhaney RN. On the miscibility of cardiolipin with 1,2-diacyl phosphoglycerides: Binary mixtures of dimyristoylphosphatidylglycerol and tetramyristoylcardiolipin. Biochim Biophys Acta. 2015 Nov;1848(11 Pt A):2878-88. doi: 10.1016/j.bbamem.2015.08.003. Epub 2015 Aug 11. PMID: 26275589.
4: Firsov AM, Kotova EA, Korepanova EA, Osipov AN, Antonenko YN. Peroxidative permeabilization of liposomes induced by cytochrome c/cardiolipin complex. Biochim Biophys Acta. 2015 Mar;1848(3):767-74. doi: 10.1016/j.bbamem.2014.11.027. Epub 2014 Dec 6. PMID: 25485477.
5: Boscia AL, Treece BW, Mohammadyani D, Klein-Seetharaman J, Braun AR, Wassenaar TA, Klösgen B, Tristram-Nagle S. X-ray structure, thermodynamics, elastic properties and MD simulations of cardiolipin/dimyristoylphosphatidylcholine mixed membranes. Chem Phys Lipids. 2014 Feb;178:1-10. doi: 10.1016/j.chemphyslip.2013.12.010. Epub 2013 Dec 28. PMID: 24378240; PMCID: PMC4026202.
6: Maniti O, Cheniour M, Lecompte MF, Marcillat O, Buchet R, Vial C, Granjon T. Acyl chain composition determines cardiolipin clustering induced by mitochondrial creatine kinase binding to monolayers. Biochim Biophys Acta. 2011 Apr;1808(4):1129-39. doi: 10.1016/j.bbamem.2011.01.005. Epub 2011 Jan 20. PMID: 21256109.
7: Frias M, Benesch MG, Lewis RN, McElhaney RN. On the miscibility of cardiolipin with 1,2-diacyl phosphoglycerides: binary mixtures of dimyristoylphosphatidylethanolamine and tetramyristoylcardiolipin. Biochim Biophys Acta. 2011 Mar;1808(3):774-83. doi: 10.1016/j.bbamem.2010.12.010. Epub 2010 Dec 21. PMID: 21182822.
8: Prossnigg F, Hickel A, Pabst G, Lohner K. Packing behaviour of two predominant anionic phospholipids of bacterial cytoplasmic membranes. Biophys Chem. 2010 Aug;150(1-3):129-35. doi: 10.1016/j.bpc.2010.04.004. Epub 2010 Apr 22. PMID: 20451316; PMCID: PMC2905515.
9: Maniti O, Cheniour M, Marcillat O, Vial C, Granjon T. Morphology modifications in negatively charged lipid monolayers upon mitochondrial creatine kinase binding. Mol Membr Biol. 2009 Apr;26(3):171-85. doi: 10.1080/09687680802698639. Epub 2009 Jan 28. PMID: 19180361.
10: Shadyro OI, Yurkova IL, Kisel MA, Brede O, Arnhold J. Radiation-induced fragmentation of cardiolipin in a model membrane. Int J Radiat Biol. 2004 Mar;80(3):239-45. doi: 10.1080/09553002310001655421. PMID: 15244377.
11: Nagamachi E, Kariyama R, Kanemasa Y. The effect of head group structure on phase transition of phospholipid membranes as determined by differential scanning calorimetry. Physiol Chem Phys Med NMR. 1985;17(3):255-60. PMID: 3841611.
