Laurdan | CAS#74515-25-6 | fluorescent marker

MedKoo Cat#: 598447 | Name: Laurdan

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Description:

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

Laurdan is a fluorescent marker.

Chemical Structure

Laurdan

CAS#74515-25-6

Theoretical Analysis

MedKoo Cat#: 598447

Name: Laurdan

CAS#: 74515-25-6

Chemical Formula: C24H35NO

Exact Mass: 353.2719

Molecular Weight: 353.55

Elemental Analysis: C, 81.53; H, 9.98; N, 3.96; O, 4.53

Price and Availability

Size	Price	Availability
25mg	USD 305.00	2 Weeks
50mg	USD 550.00	2 Weeks
100mg	USD 950.00	2 Weeks

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Synonym

Laurdan;

IUPAC/Chemical Name

1-(6-(dimethylamino)naphthalen-2-yl)dodecan-1-one

InChi Key

JHDGGIDITFLRJY-UHFFFAOYSA-N

InChi Code

InChI=1S/C24H35NO/c1-4-5-6-7-8-9-10-11-12-13-24(26)22-15-14-21-19-23(25(2)3)17-16-20(21)18-22/h14-19H,4-13H2,1-3H3

SMILES Code

CCCCCCCCCCCC(C1=CC=C2C=C(N(C)C)C=CC2=C1)=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

>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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Laurdan is a membrane-permeable fluorescent probe that displays spectral sensitivity to the phospholipid phase of the cell membrane to which it is bound.

In vitro activity:

This study seeks to gain insight into changes in the plasma membrane of live cells upon the application of osmotic stress using Laurdan, a fluorescent probe that reports on membrane organization, hydration, and dynamics. Reference: Biophys J. 2022 Jun 21;121(12):2411-2418. https://pubmed.ncbi.nlm.nih.gov/35596525/

In vivo activity:

This report measured rapid fluctuations of the normalized ratio of the emission intensity at two wavelengths of Laurdan, a membrane fluorescent dye sensitive to local membrane packing. Reference: Proc Natl Acad Sci U S A. 2012 May 8;109(19):7314-9. https://pubmed.ncbi.nlm.nih.gov/22529342/

	Solvent	mg/mL	mM
Solubility
	Chloroform	10.0	28.29
	DMF	7.1	20.00
	DMSO	12.5	35.36

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 353.55 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. Zapata-Mercado E, Azarova EV, Hristova K. Effect of osmotic stress on live cell plasma membranes, probed via Laurdan general polarization measurements. Biophys J. 2022 Jun 21;121(12):2411-2418. doi: 10.1016/j.bpj.2022.05.016. Epub 2022 May 19. PMID: 35596525; PMCID: PMC9279170. 2. Zorilă B, Necula G, Radu M, Bacalum M. Melittin Induces Local Order Changes in Artificial and Biological Membranes as Revealed by Spectral Analysis of Laurdan Fluorescence. Toxins (Basel). 2020 Nov 8;12(11):705. doi: 10.3390/toxins12110705. PMID: 33171598; PMCID: PMC7695215. 3. Sanchez SA, Tricerri MA, Gratton E. Laurdan generalized polarization fluctuations measures membrane packing micro-heterogeneity in vivo. Proc Natl Acad Sci U S A. 2012 May 8;109(19):7314-9. doi: 10.1073/pnas.1118288109. Epub 2012 Apr 23. PMID: 22529342; PMCID: PMC3358851. 4. Owen DM, Rentero C, Magenau A, Abu-Siniyeh A, Gaus K. Quantitative imaging of membrane lipid order in cells and organisms. Nat Protoc. 2011 Dec 8;7(1):24-35. doi: 10.1038/nprot.2011.419. PMID: 22157973.

In vitro protocol:

In vivo protocol:

1. Sanchez SA, Tricerri MA, Gratton E. Laurdan generalized polarization fluctuations measures membrane packing micro-heterogeneity in vivo. Proc Natl Acad Sci U S A. 2012 May 8;109(19):7314-9. doi: 10.1073/pnas.1118288109. Epub 2012 Apr 23. PMID: 22529342; PMCID: PMC3358851. 2. Owen DM, Rentero C, Magenau A, Abu-Siniyeh A, Gaus K. Quantitative imaging of membrane lipid order in cells and organisms. Nat Protoc. 2011 Dec 8;7(1):24-35. doi: 10.1038/nprot.2011.419. PMID: 22157973.

1: Mazeres S, Joly E, Lopez A, Tardin C. Characterization of M-laurdan, a versatile probe to explore order in lipid membranes. Version 2. F1000Res. 2014 Jul 25 [revised 2014 Jan 1];3:172. eCollection 2014. PubMed PMID: 25485094; PubMed Central PMCID: PMC4243762. 2: 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. Epub 2016 Nov 15. PubMed PMID: 27806200. 3: Titova TY, Artyukhov VY, Zharkova OM, Morozova JP. Spectral-luminescent properties of laurdan molecule. Spectrochim Acta A Mol Biomol Spectrosc. 2014 Apr 24;124:64-9. doi: 10.1016/j.saa.2013.12.097. Epub 2014 Jan 7. PubMed PMID: 24463241. 4: Vequi-Suplicy CC, Coutinho K, Lamy MT. New insights on the fluorescent emission spectra of Prodan and Laurdan. J Fluoresc. 2015 May;25(3):621-9. doi: 10.1007/s10895-015-1545-x. Epub 2015 Mar 10. PubMed PMID: 25753230. 5: Golfetto O, Hinde E, Gratton E. Laurdan fluorescence lifetime discriminates cholesterol content from changes in fluidity in living cell membranes. Biophys J. 2013 Mar 19;104(6):1238-47. doi: 10.1016/j.bpj.2012.12.057. Epub 2013 Mar 19. PubMed PMID: 23528083; PubMed Central PMCID: PMC3602759. 6: 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. PubMed PMID: 23311388. 7: Golfetto O, Hinde E, Gratton E. The Laurdan spectral phasor method to explore membrane micro-heterogeneity and lipid domains in live cells. Methods Mol Biol. 2015;1232:273-90. doi: 10.1007/978-1-4939-1752-5_19. PubMed PMID: 25331141. 8: Bacalum M, Zorilă B, Radu M. Fluorescence spectra decomposition by asymmetric functions: Laurdan spectrum revisited. Anal Biochem. 2013 Sep 15;440(2):123-9. doi: 10.1016/j.ab.2013.05.031. Epub 2013 Jun 6. PubMed PMID: 23747535. 9: Strohmeier A, Först G, Tauber P, Schubert R. Membrane/Water Partition Coefficients of Bile Salts Determined Using Laurdan as a Fluorescent Probe. Biophys J. 2016 Oct 18;111(8):1714-1723. doi: 10.1016/j.bpj.2016.08.040. PubMed PMID: 27760358; PubMed Central PMCID: PMC5072983. 10: Bonaventura G, Barcellona ML, Golfetto O, Nourse JL, Flanagan LA, Gratton E. Laurdan monitors different lipids content in eukaryotic membrane during embryonic neural development. Cell Biochem Biophys. 2014 Nov;70(2):785-94. doi: 10.1007/s12013-014-9982-8. PubMed PMID: 24839062; PubMed Central PMCID: PMC4228983. 11: Carravilla P, Nieva JL, Goñi FM, Requejo-Isidro J, Huarte N. Two-photon Laurdan studies of the ternary lipid mixture DOPC:SM:cholesterol reveal a single liquid phase at sphingomyelin:cholesterol ratios lower than 1. Langmuir. 2015 Mar 10;31(9):2808-17. doi: 10.1021/la504251u. Epub 2015 Feb 25. PubMed PMID: 25658036. 12: 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. PubMed PMID: 22184757; PubMed Central PMCID: PMC3276485. 13: Harris FM, Best KB, Bell JD. Use of laurdan fluorescence intensity and polarization to distinguish between changes in membrane fluidity and phospholipid order. Biochim Biophys Acta. 2002 Sep 20;1565(1):123-8. PubMed PMID: 12225860. 14: Vequi-Suplicy CC, Coutinho K, Lamy MT. Electric dipole moments of the fluorescent probes Prodan and Laurdan: experimental and theoretical evaluations. Biophys Rev. 2014 Mar;6(1):63-74. doi: 10.1007/s12551-013-0129-8. Epub 2014 Jan 14. Review. PubMed PMID: 28509963; PubMed Central PMCID: PMC5425710. 15: Pokorna S, Jurkiewicz P, Vazdar M, Cwiklik L, Jungwirth P, Hof M. Does fluoride disrupt hydrogen bond network in cationic lipid bilayer? Time-dependent fluorescence shift of Laurdan and molecular dynamics simulations. J Chem Phys. 2014 Dec 14;141(22):22D516. doi: 10.1063/1.4898798. PubMed PMID: 25494787. 16: Malacrida L, Astrada S, Briva A, Bollati-Fogolín M, Gratton E, Bagatolli LA. Spectral phasor analysis of LAURDAN fluorescence in live A549 lung cells to study the hydration and time evolution of intracellular lamellar body-like structures. Biochim Biophys Acta. 2016 Nov;1858(11):2625-2635. doi: 10.1016/j.bbamem.2016.07.017. Epub 2016 Jul 30. PubMed PMID: 27480804; PubMed Central PMCID: PMC5045802. 17: Vequi-Suplicy CC, Lamy MT, Marquezin CA. The new fluorescent membrane probe Ahba: a comparative study with the largely used Laurdan. J Fluoresc. 2013 May;23(3):479-86. doi: 10.1007/s10895-013-1172-3. Epub 2013 Feb 9. PubMed PMID: 23397490. 18: Ionescu D, Ganea C. A study of quercetin effects on phospholipid membranes containing cholesterol using Laurdan fluorescence. Eur Biophys J. 2012 Feb 3. [Epub ahead of print] PubMed PMID: 22302013. 19: Suga K, Akizaki K, Umakoshi H. Quantitative Monitoring of Microphase Separation Behaviors in Cationic Liposomes Using HHC, DPH, and Laurdan: Estimation of the Local Electrostatic Potentials in Microdomains. Langmuir. 2016 Apr 19;32(15):3630-6. doi: 10.1021/acs.langmuir.5b04682. Epub 2016 Apr 6. PubMed PMID: 27022833. 20: Nemkovich NA, Detert H, Roeder N. Electrooptical Absorption Measurements (EOAM) Testify Existence of two Conformers of Prodan and Laurdan with Different Dipole Moments in Equilibrium Ground and Franck-Condon Excited State. J Fluoresc. 2016 Sep;26(5):1563-72. doi: 10.1007/s10895-016-1809-0. Epub 2016 Jul 11. PubMed PMID: 27396483.