Tetramyristoylcardiolipin ammonium salt | CAS#unknown | Cationic lipid

MedKoo Cat#: 465243 | Name: Tetramyristoylcardiolipin ammonium

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tetramyristoylcardiolipin is a is a cationic lipid for RNA and vaccine delivery.

Chemical Structure

Tetramyristoylcardiolipin ammonium

CAS#63988-20-5

Theoretical Analysis

MedKoo Cat#: 465243

Name: Tetramyristoylcardiolipin ammonium

CAS#: 63988-20-5

Chemical Formula: C65H132N2O17P2

Exact Mass: 1274.9001

Molecular Weight: 1275.72

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

Instruction

View handling instruction

Preparing Stock Solutions

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

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.