P6516

Sigma-Aldrich

Poly-L-lysine hydrobromide

greener alternative

mol wt 4,000-15,000 by viscosity

CAS Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.26

Quality Level

form

solid

mol wt

≤15,000 by MALLS
4,000-15,000 by viscosity

greener alternative product score

old score: 11
new score: 5
Find out more about DOZN™ Scoring

greener alternative product characteristics

Atom Economy
Less Hazardous Chemical Syntheses
Use of Renewable Feedstocks
Learn more about the Principles of Green Chemistry.

application(s)

cell analysis: suitable
cell culture | mammalian: suitable

color

white to off-white

greener alternative category

Re-engineered

storage temp.

−20°C

SMILES string

Cl.NCCCCC(N)C(O)=O

InChI

1S/C18H38N6O4/c19-10-4-1-7-13(22)16(25)23-14(8-2-5-11-20)17(26)24-15(18(27)28)9-3-6-12-21/h13-15H,1-12,19-22H2,(H,23,25)(H,24,26)(H,27,28)/t13-,14-,15-/m0/s1

InChI key

WBSCNDJQPKSPII-KKUMJFAQSA-N

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Application

Poly-L-lysine polymers can be used in promoting cell adhesion to solid substrates, conjugation to methotrexate for increased drug transport, microencapsulation of islets, cell microencapsulation technology, microarray glass slide coating, and chromosomal preparations. Lower molecular weight poly-L-lysine (30,000-70,000) is less viscuous in solution, but higher molecular weight versions provide more attachment sites per molecule. Poly-L-lysine hydrobromide has been used:
  • as a component of polyplexes and in DNA condensation experiments
  • for coating circular mica disks for atomic force microscopy studies and SuperFrost glass slides for immunofluorescence studies of in HL-60 cells
  • as a reference standard for generating calibration curve for the quantification of ε- Poly-L-lysine

Packaging

25, 100, 500 mg in poly bottle
1 g in poly bottle

Biochem/physiol Actions

Poly-L-lysine is a nonspecific attachment factor for cells useful in promoting cell adhesion to solid substrates by enhancing electrostatic interaction between negatively charged ions of the cell membrane and the culture surface. When it is absorbed to the cell culture surface, poly-L-lysine functions to increase the number of positively charged sites available for cell binding. With cells that can digest poly-L-lysine, poly-D-lysine should be used as the attachment factor.

Components

Poly-L-lysine is a positively charged amino acid polymer with approximately one HBr per lysine residue. The hydrobromide allows the poly-L-lysine to be in a crystalline form soluble in water. A small amount of product may be found in the beta structure because the HBr interferes with hydrogen bonding between amino and either the carboxyl groups or N or O containing moieties.

Caution

Sterile solutions are stable for up to 2 years when stored at 2-8°C. It should be stored desiccated at -20°C.

Preparation Note

This product has a molecular weight of 4,000-15,000. To remove the HBr, dissolve this product in a neutral buffer and dialyze to remove the salts. None of the poly-L-lysine products have been exposed to trifluoroacetic acid and are dialyzed to remove any monomers, dimmers, or trimers, confirmed by thin layer chromatography. In general, to use this product as an attachment factor, add 50 mL of sterile tissue culture grade water to 5 mg of poly-lysine, and aseptically coat the surface with 1 mL per 25 cm2 of solution. After 5 minutes, remove the solution through aspiration and thoroughly rinse the surface. Let dry for two hours before introducing cells and medium.

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

AFM imaging of bacteria in liquid media immobilized on gelatin coated mica surfaces
Doktycz MJ, et al.
Ultramicroscopy, 97(1-4), 209-216 (2003)
DNA condensation by poly-L-lysine at the single molecule level: role of DNA concentration and polymer length
Mann A, et al.
Journal of Controlled Release : Official Journal of the Controlled Release Society, 125(3), 252-262 (2008)
Epsilon-Polylysine Fermentation and its Recovery Using Carboxymethyl Cellulose (CMC)-Conjugated Magnetite
Wibowo N, et al.
Separation Science and Technology, 48(7), 1086-1092 (2013)
Retinoic acid differentiation of HL-60 cells promotes cytoskeletal polarization
Olins AL, et al.
Experimental Cell Research, 254(1), 130-142 (2000)
Arlin Jose Amali et al.
Chemical communications (Cambridge, England), 48(6), 856-858 (2011-11-30)
Counter-ion condensation of Poly(L-Lysine) in the presence of pyranine-3 generates spherical coacervates, which then template the assembly of silica nanoparticles to form microcapsule structures that dynamically control the optical ratiometric sensing of both the change in pH and release of...
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