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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

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
Rong Liu et al.
International journal of nanomedicine, 7, 4433-4446 (2012-08-28)
Two methoxyl poly(ethylene glycol)-poly(L-histidine)-poly(L-lactide) (mPEG-PH-PLLA) triblock copolymers with different poly(L-histidine) chain lengths were synthesized. The morphology and biocompatibility of these self-assembled nanoparticles was investigated. Doxorubicin, an antitumor drug, was trapped in the nanoparticles to explore their drug-release behavior. The drug-loaded
Electrochemical determination of ascorbic acid and paracetamol in pharmaceutical formulations using a glassy carbon electrode modified with multi-wall carbon nanotubes dispersed in polyhistidine
Dalmasso PR, et al.
Sensors and Actuators B, Chemical, 173(5), 732-736 (2012)
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
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Poly(Amino Acid) Block Copolymers for Drug Delivery and other Biomedical Applications

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