Kdo2-Lipid A (KLA) | CAS# 1246298-62-3 | endotoxin activity

MedKoo Cat#: 412723 | Name: Kdo2-Lipid A (KLA)

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Description:

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

Kdo2-Lipid A (KLA) is a nearly homogeneous Re lipopolysaccharide (LPS) substructure with endotoxin activity equal to that of native LPS. KLA is comparable to LPS and its activity is reduced by >103 in cells from TLR-4 deficient mice. The advantage of KLA over LPS is that it is a reproducible, defined natural product, and it can be detected by ESI/MS at the low concentrations used to stimulate animal cells. The purity of KLA should also facilitate the structural analysis of its complexes with signaling receptors, such as TLR-4/MD2.

Chemical Structure

Kdo2-Lipid A (KLA)

CAS#1246298-62-3

Theoretical Analysis

MedKoo Cat#: 412723

Name: Kdo2-Lipid A (KLA)

CAS#: 1246298-62-3

Chemical Formula: C110H214N6O39P2

Exact Mass: 2305.4422

Molecular Weight: 2306.87

Elemental Analysis: C, 57.27; H, 9.35; N, 3.64; O, 27.05; P, 2.69

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 550.00	2 Weeks

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Synonym

Kdo2-Lipid A (KLA); Di[3-deoxy-D-manno-octulosonyl]-lipid A (ammonium salt)

IUPAC/Chemical Name

ammonium (2R,4R,6R)-2-(((2R,4R,5R,6R)-2-carboxylato-6-((R)-1,2-dihydroxyethyl)-2-(((2R,3S,4R,5R,6R)-5-((R)-3-(dodecanoyloxy)tetradecanamido)-6-(((2R,3S,4R,5R,6R)-3-hydroxy-6-((hydroxyoxidophosphoryl)oxy)-5-((R)-3-hydroxytetradecanamido)-4-(((R)-3-hydroxytetradecanoyl)oxy)tetrahydro-2H-pyran-2-yl)methoxy)-3-((hydroxyoxidophosphoryl)oxy)-4-(((R)-3-(tetradecanoyloxy)tetradecanoyl)oxy)tetrahydro-2H-pyran-2-yl)methoxy)-5-hydroxytetrahydro-2H-pyran-4-yl)oxy)-6-((R)-1,2-dihydroxyethyl)-4,5-dihydroxytetrahydro-2H-pyran-2-carboxylate

InChi Key

HBSUHPVFGADBOQ-IIEJLJSISA-N

InChi Code

InChI=1S/C110H202N2O39P2.4H3N/c1-7-13-19-25-31-37-38-44-50-56-62-68-92(123)142-82(66-60-54-48-42-35-29-23-17-11-5)72-94(125)146-104-96(112-90(121)71-81(65-59-53-47-41-34-28-22-16-10-4)141-91(122)67-61-55-49-43-36-30-24-18-12-6)105(144-88(102(104)150-152(133,134)135)78-140-109(107(129)130)74-86(98(127)101(148-109)85(119)76-114)147-110(108(131)132)73-83(117)97(126)100(149-110)84(118)75-113)139-77-87-99(128)103(145-93(124)70-80(116)64-58-52-46-40-33-27-21-15-9-3)95(106(143-87)151-153(136,137)138)111-89(120)69-79(115)63-57-51-45-39-32-26-20-14-8-2;;;;/h79-88,95-106,113-119,126-128H,7-78H2,1-6H3,(H,111,120)(H,112,121)(H,129,130)(H,131,132)(H2,133,134,135)(H2,136,137,138);4*1H3/t79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,95-,96-,97?,98-,99-,100-,101-,102-,103-,104-,105-,106-,109-,110-;;;;/m1..../s1

SMILES Code

O[C@H]([C@@H](CO[C@@H]([C@@H]1NC(C[C@H](OC(CCCCCCCCCCC)=O)CCCCCCCCCCC)=O)O[C@H](CO[C@]2(C([O-])=O)C[C@@H](O[C@@]3(C([O-])=O)O[C@H]([C@H](O)CO)C(O)[C@H](O)C3)[C@@H](O)[C@@H]([C@H](O)CO)O2)[C@@H](OP([O-])(O)=O)[C@@H]1OC(C[C@H](OC(CCCCCCCCCCCCC)=O)CCCCCCCCCCC)=O)O[C@H](OP(O)([O-])=O)[C@@H]4NC(C[C@H](O)CCCCCCCCCCC)=O)[C@@H]4OC(C[C@H](O)CCCCCCCCCCC)=O.[NH4+].[NH4+].[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

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Kdo2-Lipid A ammonium is highly selective for TLR4. Kdo2-Lipid A ammonium stimulates the release of both TNF and PGE2.

In vitro activity:

Nonetheless, the activated RAW264.7 cells have a higher number of sphingolipids per cell because KLA inhibits cell division; thus, the cells are larger and contain increased numbers of membrane vacuoles termed autophagosomes, which were detected by the protein marker GFP-LC3. Reference: J Biol Chem. 2010 Dec 3;285(49):38568-79. https://pubmed.ncbi.nlm.nih.gov/20876532/

In vivo activity:

Kdo(2)-Lipid A is comparable to LPS by these criteria. Its activity is reduced by >10(3) in cells from TLR-4-deficient mice. Reference: J Lipid Res. 2006 May;47(5):1097-111. https://pubmed.ncbi.nlm.nih.gov/16479018/

Preparing Stock Solutions

The following data is based on the product molecular weight 2,306.87 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:

1. Sims K, Haynes CA, Kelly S, Allegood JC, Wang E, Momin A, Leipelt M, Reichart D, Glass CK, Sullards MC, Merrill AH Jr. Kdo2-lipid A, a TLR4-specific agonist, induces de novo sphingolipid biosynthesis in RAW264.7 macrophages, which is essential for induction of autophagy. J Biol Chem. 2010 Dec 3;285(49):38568-79. doi: 10.1074/jbc.M110.170621. Epub 2010 Sep 27. PMID: 20876532; PMCID: PMC2992289. 2. Raetz CR, Garrett TA, Reynolds CM, Shaw WA, Moore JD, Smith DC Jr, Ribeiro AA, Murphy RC, Ulevitch RJ, Fearns C, Reichart D, Glass CK, Benner C, Subramaniam S, Harkewicz R, Bowers-Gentry RC, Buczynski MW, Cooper JA, Deems RA, Dennis EA. Kdo2-Lipid A of Escherichia coli, a defined endotoxin that activates macrophages via TLR-4. J Lipid Res. 2006 May;47(5):1097-111. doi: 10.1194/jlr.M600027-JLR200. Epub 2006 Feb 14. PMID: 16479018.

In vitro protocol:

In vivo protocol:

1. Raetz CR, Garrett TA, Reynolds CM, Shaw WA, Moore JD, Smith DC Jr, Ribeiro AA, Murphy RC, Ulevitch RJ, Fearns C, Reichart D, Glass CK, Benner C, Subramaniam S, Harkewicz R, Bowers-Gentry RC, Buczynski MW, Cooper JA, Deems RA, Dennis EA. Kdo2-Lipid A of Escherichia coli, a defined endotoxin that activates macrophages via TLR-4. J Lipid Res. 2006 May;47(5):1097-111. doi: 10.1194/jlr.M600027-JLR200. Epub 2006 Feb 14. PMID: 16479018.

1: Sims K, Haynes CA, Kelly S, Allegood JC, Wang E, Momin A, Leipelt M, Reichart D, Glass CK, Sullards MC, Merrill AH Jr. Kdo2-lipid A, a TLR4-specific agonist, induces de novo sphingolipid biosynthesis in RAW264.7 macrophages, which is essential for induction of autophagy. J Biol Chem. 2010 Dec 3;285(49):38568-79. doi: 10.1074/jbc.M110.170621. Epub 2010 Sep 27. PMID: 20876532; PMCID: PMC2992289. 2: Crittenden CM , Morrison LJ , Fitzpatrick MD , Myers AP , Novelli ET , Rosenberg J , Akin LD , Srinivasa V , Shear JB , Brodbelt JS . Towards mapping electrostatic interactions between Kdo2-lipid A and cationic antimicrobial peptides via ultraviolet photodissociation mass spectrometry. Analyst. 2018 Jul 23;143(15):3607-3618. doi: 10.1039/c8an00652k. PMID: 29968868; PMCID: PMC6056329. 3: Chen WW, Chao YJ, Chang WH, Chan JF, Hsu YH. Phosphatidylglycerol Incorporates into Cardiolipin to Improve Mitochondrial Activity and Inhibits Inflammation. Sci Rep. 2018 Mar 20;8(1):4919. doi: 10.1038/s41598-018-23190-z. PMID: 29559686; PMCID: PMC5861085. 4: Dinasarapu AR, Gupta S, Ram Maurya M, Fahy E, Min J, Sud M, Gersten MJ, Glass CK, Subramaniam S. A combined omics study on activated macrophages--enhanced role of STATs in apoptosis, immunity and lipid metabolism. Bioinformatics. 2013 Nov 1;29(21):2735-43. doi: 10.1093/bioinformatics/btt469. Epub 2013 Aug 26. PMID: 23981351; PMCID: PMC3799469. 5: Gregus AM, Buczynski MW, Dumlao DS, Norris PC, Rai G, Simeonov A, Maloney DJ, Jadhav A, Xu Q, Wei SC, Fitzsimmons BL, Dennis EA, Yaksh TL. Inhibition of spinal 15-LOX-1 attenuates TLR4-dependent, nonsteroidal anti-inflammatory drug- unresponsive hyperalgesia in male rats. Pain. 2018 Dec;159(12):2620-2629. doi: 10.1097/j.pain.0000000000001373. PMID: 30130298; PMCID: PMC6237621. 6: Zhang G, Zhao L, Zhu J, Feng Y, Wu X. Anti-inflammatory activities and glycerophospholipids metabolism in KLA-stimulated RAW 264.7 macrophage cells by diarylheptanoids from the rhizomes of Alpinia officinarum. Biomed Chromatogr. 2018 Feb;32(2). doi: 10.1002/bmc.4094. Epub 2017 Oct 2. PMID: 28906002. 7: Chang WH, Ting HC, Chen WW, Chan JF, Hsu YH. Omega-3 and omega-6 fatty acid differentially impact cardiolipin remodeling in activated macrophage. Lipids Health Dis. 2018 Aug 28;17(1):201. doi: 10.1186/s12944-018-0845-y. PMID: 30153842; PMCID: PMC6114728. 8: Maurya MR, Gupta S, Li X, Fahy E, Dinasarapu AR, Sud M, Brown HA, Glass CK, Murphy RC, Russell DW, Dennis EA, Subramaniam S. Analysis of inflammatory and lipid metabolic networks across RAW264.7 and thioglycolate-elicited macrophages. J Lipid Res. 2013 Sep;54(9):2525-42. doi: 10.1194/jlr.M040212. Epub 2013 Jun 17. PMID: 23776196; PMCID: PMC3735949. 9: Kihara Y, Gupta S, Maurya MR, Armando A, Shah I, Quehenberger O, Glass CK, Dennis EA, Subramaniam S. Modeling of eicosanoid fluxes reveals functional coupling between cyclooxygenases and terminal synthases. Biophys J. 2014 Feb 18;106(4):966-75. doi: 10.1016/j.bpj.2014.01.015. PMID: 24559999; PMCID: PMC3945033. 10: Oishi Y, Hayashi S, Isagawa T, Oshima M, Iwama A, Shimba S, Okamura H, Manabe I. Bmal1 regulates inflammatory responses in macrophages by modulating enhancer RNA transcription. Sci Rep. 2017 Aug 1;7(1):7086. doi: 10.1038/s41598-017-07100-3. PMID: 28765524; PMCID: PMC5539165.