WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H463868
CAS#: 959839-06-6
Description: C-Laurdan is a fluorescent probe for imaging lipid rafts. It is used to detect membrane polairty via one and two-photon fluorecence imaging.
Hodoodo Cat#: H463868
Name: C-Laurdan
CAS#: 959839-06-6
Chemical Formula: C25H35NO3
Exact Mass: 397.26
Molecular Weight: 397.559
Elemental Analysis: C, 75.53; H, 8.87; N, 3.52; O, 12.07
Synonym: C-Laurdan; C Laurdan;
IUPAC/Chemical Name: N-(6-dodecanoylnaphthalen-2-yl)-N-methylglycine
InChi Key: INSWREUMXDGFSD-UHFFFAOYSA-N
InChi Code: InChI=1S/C25H35NO3/c1-3-4-5-6-7-8-9-10-11-12-24(27)22-14-13-21-18-23(16-15-20(21)17-22)26(2)19-25(28)29/h13-18H,3-12,19H2,1-2H3,(H,28,29)
SMILES Code: CCCCCCCCCCCC(C1=CC2=C(C=C1)C=C(C=C2)N(C)CC(O)=O)=O
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: >2 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:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 397.56 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: Danylchuk DI, Sezgin E, Chabert P, Klymchenko AS. Redesigning Solvatochromic Probe Laurdan for Imaging Lipid Order Selectively in Cell Plasma Membranes. Anal Chem. 2020 Nov 3;92(21):14798-14805. doi: 10.1021/acs.analchem.0c03559. Epub 2020 Oct 12. PMID: 33044816.
2: Augenstreich J, Haanappel E, Sayes F, Simeone R, Guillet V, Mazeres S, Chalut C, Mourey L, Brosch R, Guilhot C, Astarie-Dequeker C. Phthiocerol Dimycocerosates From Mycobacterium tuberculosis Increase the Membrane Activity of Bacterial Effectors and Host Receptors. Front Cell Infect Microbiol. 2020 Aug 14;10:420. doi: 10.3389/fcimb.2020.00420. PMID: 32923411; PMCID: PMC7456886.
3: Browning RJ, Aron M, Booth A, Rademeyer P, Wing S, Brans V, Shrivastava S, Carugo D, Stride E. Spectral Imaging for Microbubble Characterization. Langmuir. 2020 Jan 21;36(2):609-617. doi: 10.1021/acs.langmuir.9b03828. Epub 2020 Jan 9. PMID: 31855435.
4: Salinas ML, Fuentes NR, Choate R, Wright RC, McMurray DN, Chapkin RS. AdipoRon Attenuates Wnt Signaling by Reducing Cholesterol-Dependent Plasma Membrane Rigidity. Biophys J. 2020 Feb 25;118(4):885-897. doi: 10.1016/j.bpj.2019.09.009. Epub 2019 Sep 16. PMID: 31630812; PMCID: PMC7036725.
5: Aron M, Vince O, Gray M, Mannaris C, Stride E. Investigating the Role of Lipid Transfer in Microbubble-Mediated Drug Delivery. Langmuir. 2019 Oct 8;35(40):13205-13215. doi: 10.1021/acs.langmuir.9b02404. Epub 2019 Sep 27. PMID: 31517490.
6: Bianchi F, Pereno V, George JH, Thompson MS, Ye H. Membrane Mechanical Properties Regulate the Effect of Strain on Spontaneous Electrophysiology in Human iPSC-Derived Neurons. Neuroscience. 2019 Apr 15;404:165-174. doi: 10.1016/j.neuroscience.2019.02.014. Epub 2019 Feb 26. PMID: 30817953.
7: Mazeres S, Fereidouni F, Joly E. Using spectral decomposition of the signals from laurdan-derived probes to evaluate the physical state of membranes in live cells. F1000Res. 2017 Jun 1;6:763. doi: 10.12688/f1000research.11577.2. PMID: 28663788; PMCID: PMC5473435.
8: Aron M, Browning R, Carugo D, Sezgin E, Bernardino de la Serna J, Eggeling C, Stride E. Spectral imaging toolbox: segmentation, hyperstack reconstruction, and batch processing of spectral images for the determination of cell and model membrane lipid order. BMC Bioinformatics. 2017 May 12;18(1):254. doi: 10.1186/s12859-017-1656-2. PMID: 28494801; PMCID: PMC5427590.
9: Osella S, Murugan NA, Jena NK, Knippenberg S. Investigation into Biological Environments through (Non)linear Optics: A Multiscale Study of Laurdan Derivatives. J Chem Theory Comput. 2016 Dec 13;12(12):6169-6181. doi: 10.1021/acs.jctc.6b00906. Epub 2016 Nov 15. PMID: 27806200.
10: Sezgin E, Waithe D, Bernardino de la Serna J, Eggeling C. Spectral imaging to measure heterogeneity in membrane lipid packing. Chemphyschem. 2015 May 18;16(7):1387-94. doi: 10.1002/cphc.201402794. Epub 2015 Mar 5. PMID: 25755090; PMCID: PMC4539592.
11: Mazeres S, Joly E, Lopez A, Tardin C. Characterization of M-laurdan, a versatile probe to explore order in lipid membranes. F1000Res. 2014 Jul 25;3:172. doi: 10.12688/f1000research.4805.2. PMID: 25485094; PMCID: PMC4243762.
12: Barucha-Kraszewska J, Kraszewski S, Ramseyer C. Will C-Laurdan dethrone Laurdan in fluorescent solvent relaxation techniques for lipid membrane studies? Langmuir. 2013 Jan 29;29(4):1174-82. doi: 10.1021/la304235r. Epub 2013 Jan 11. PMID: 23311388.
13: Yurlova L, Kahya N, Aggarwal S, Kaiser HJ, Chiantia S, Bakhti M, Pewzner- Jung Y, Ben-David O, Futerman AH, Brügger B, Simons M. Self-segregation of myelin membrane lipids in model membranes. Biophys J. 2011 Dec 7;101(11):2713-20. doi: 10.1016/j.bpj.2011.10.026. PMID: 22261060; PMCID: PMC3297774.
14: Dodes Traian MM, González Flecha FL, Levi V. Imaging lipid lateral organization in membranes with C-laurdan in a confocal microscope. J Lipid Res. 2012 Mar;53(3):609-16. doi: 10.1194/jlr.D021311. Epub 2011 Dec 19. PMID: 22184757; PMCID: PMC3276485.
15: Kaiser HJ, Surma MA, Mayer F, Levental I, Grzybek M, Klemm RW, Da Cruz S, Meisinger C, Müller V, Simons K, Lingwood D. Molecular convergence of bacterial and eukaryotic surface order. J Biol Chem. 2011 Nov 25;286(47):40631-7. doi: 10.1074/jbc.M111.276444. Epub 2011 Sep 30. PMID: 21965671; PMCID: PMC3220465.
16: Ekholm O, Jaikishan S, Lönnfors M, Nyholm TK, Slotte JP. Membrane bilayer properties of sphingomyelins with amide-linked 2- or 3-hydroxylated fatty acids. Biochim Biophys Acta. 2011 Mar;1808(3):727-32. doi: 10.1016/j.bbamem.2010.12.006. Epub 2010 Dec 15. PMID: 21167130.
17: Kaiser HJ, Lingwood D, Levental I, Sampaio JL, Kalvodova L, Rajendran L, Simons K. Order of lipid phases in model and plasma membranes. Proc Natl Acad Sci U S A. 2009 Sep 29;106(39):16645-50. doi: 10.1073/pnas.0908987106. Epub 2009 Sep 15. PMID: 19805351; PMCID: PMC2757813.
18: Yi JS, Choo HJ, Cho BR, Kim HM, Kim YN, Ham YM, Ko YG. Ginsenoside Rh2 induces ligand-independent Fas activation via lipid raft disruption. Biochem Biophys Res Commun. 2009 Jul 24;385(2):154-9. doi: 10.1016/j.bbrc.2009.05.028. Epub 2009 May 13. PMID: 19445898.
19: Klemm RW, Ejsing CS, Surma MA, Kaiser HJ, Gerl MJ, Sampaio JL, de Robillard Q, Ferguson C, Proszynski TJ, Shevchenko A, Simons K. Segregation of sphingolipids and sterols during formation of secretory vesicles at the trans- Golgi network. J Cell Biol. 2009 May 18;185(4):601-12. doi: 10.1083/jcb.200901145. Epub 2009 May 11. PMID: 19433450; PMCID: PMC2711577.
20: Kim HM, Choo HJ, Jung SY, Ko YG, Park WH, Jeon SJ, Kim CH, Joo T, Cho BR. A two-photon fluorescent probe for lipid raft imaging: C-laurdan. Chembiochem. 2007 Mar 26;8(5):553-9. doi: 10.1002/cbic.200700003. PMID: 17300111.
