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P9386

Sigma-Aldrich

Poly-L-histidine

mol wt 5,000-25,000

Synonym(s):

L-Histidine homopolymer

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About This Item

CAS Number:
26062-48-6
MDL number:
MFCD00166382
UNSPSC Code:
12352209
PubChem Substance ID:
24899031
NACRES:
NA.26

form

powder or solid

Quality Level

200

mol wt

5,000-25,000

color

white to light yellow

application(s)

cell analysis

storage temp.

−20°C

SMILES string

[N+H3][C@@H](Cc1[nH]cnc1)C(=O)[O-]

InChI

1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m0/s1

InChI key

HNDVDQJCIGZPNO-YFKPBYRVSA-N

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General description

Poly-L-histidine is an amphoteric compound. The imidazole ring in its structure enables protonation−deprotonation.

Application

Poly-L-histidine has been used:
  • as a polycation for the dispersion of multi-wall carbon nanotubes (MWCNTs)
  • as a polyionic compound to investigate its ability to rupture extracellular enveloped virus membrane
  • in screening its anti-prion activity in cell based and in vivo anti-prion assay

Biochem/physiol Actions

Poly-L-histidine (Phis) copolymers are biocompatible, pH responsive and are less toxic. It exhibits endolysosomal escape funcationality. The copolymer of Phis with poly(ethylene glycol)−poly(d,l-lactide) (PEG-PLA) is effective in delivering doxorubicin. pH sensitive poly(l-histidine) copolymer micelles have application in delivering anticancer drugs in acidic microenvironment.

Analysis Note

Molecular weight by MALLS.

Other Notes

For additional technical information on polyamino acids please visit the Polyamino acid FAQ resource.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000379133
0000371765
0000344536
0000325296
0000315700

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Poly-L-histidine inhibits prion propagation in a prion-infected cell line
Honda R, et al.
Prion, 12(3-4), 226-233 (2018)
Wooram Park et al.
Biomaterials, 33(34), 8848-8857 (2012-09-11)
For long-term, sustained protein delivery, a new, star-shaped block copolymer composed of methoxy poly(ethylene glycol) (mPEG), branched oligoethylenimine (bOEI), and poly(l-histidine) (pHis) was synthesized via the multi-initiation and ring-opening polymerization (ROP) of His N-carboxy anhydride (NCA) on bOEI with a
Preparation and evaluation of poly (L-histidine) based pH-sensitive micelles for intracellular delivery of doxorubicin against MCF-7/ADR cells
Jia N, et al.
Asian Journal of Pharmaceutical Sciences , 12(5), 433-441 (2017)
Masaharu Kondo et al.
Biomacromolecules, 13(2), 432-438 (2012-01-14)
A polyhistidine (His) tag was fused to the C- or N-terminus of the light-harvesting (LH1)-α chain of the photosynthetic antenna core complex (LH1-RC) from Rhodobacter sphaeroides to allow immobilization of the complex on a solid substrate with defined orientation. His-tagged
Frank Morgner et al.
Sensors (Basel, Switzerland), 11(10), 9667-9684 (2011-12-14)
Förster resonance energy transfer (FRET) from luminescent terbium complexes (LTC) as donors to semiconductor quantum dots (QDs) as acceptors allows extraordinary large FRET efficiencies due to the long Förster distances afforded. Moreover, time-gated detection permits an efficient suppression of autofluorescent
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Poly(Amino Acid) Block Copolymers for Drug Delivery and other Biomedical Applications

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