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870320P

Avanti

N-palmitoyl homocysteine (PHC)

Avanti Research™ - A Croda Brand 870320P, powder

Synonyme(s) :

N-palmitoyl homocysteine (ammonium salt)

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About This Item

Formule empirique (notation de Hill):
C20H42N2O3S
Numéro CAS:
474942-73-9
Poids moléculaire :
390.62
Code UNSPSC :
12352211
Nomenclature NACRES :
NA.25

Forme

powder

Conditionnement

pkg of 1 × 25 mg (870320P-25mg)

Fabricant/nom de marque

Avanti Research™ - A Croda Brand 870320P

Conditions d'expédition

dry ice

Température de stockage

−20°C

Chaîne SMILES 

[O-]C(C(NC(CCCCCCCCCCCCCCC)=O)CCS)=O.[NH4+]

InChI

1S/C20H39NO3S.H3N/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(22)21-18(16-17-25)20(23)24;/h18,25H,2-17H2,1H3,(H,21,22)(H,23,24);1H3

Clé InChI

WUXWCXRWTBPUKZ-UHFFFAOYSA-N

Description générale

N-palmitoyl homocysteine (PHC) is a pH sensitive head group modified lipid.

Application

N-palmitoyl homocysteine (PHC) has been used in the synthesis of micelle-encapsulated temozolomide (TMZ) and targeted rapamycin micelles (TRaM).

Actions biochimiques/physiologiques

Liposomes containing pH-sensitive molecules facilitate site-specific drug release in response to the change of pH in the surrounding serum. They deliver drugs or gene fragments into the cytoplasm through the endocytotic pathway. Unlike plain liposomes, pH-sensitive liposomes effectively protect drugs and other encapsulated contents such as enzymes, plasmids, proteins and peptides from being potentially degraded at the lysosomal level. They have a wide range of clinical applications such as a carrier of potent drugs for cancer, pulmonary and infectious diseases, a vaccine adjuvant and a vehicle for contrasting agents during imaging. In addition, pH-sensitive liposomes also facilitate the transport of nucleic acids during gene therapy. DOPE liposomes containing PHC deliver their contents at the early endosome.

Conditionnement

5 mL Amber Glass Screw Cap Vial (870320P-25mg)

Informations légales

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

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D Collins et al.
Biochimica et biophysica acta, 987(1), 47-55 (1989-12-11)
By combining dioleoylphosphatidylethanolamine (DOPE) with oleic acid (OA), palmitoylhomocysteine (PHC) or dipalmitoylsuccinylglycerol (DPSG) we have prepared pH-sensitive liposomes with different acid sensitivities. DOPE/OA liposomes are the most acid sensitive, while DOPE/DPSG liposomes are the least acid sensitive. Incubation of DOPE/OA
M B Yatvin et al.
Science (New York, N.Y.), 210(4475), 1253-1255 (1980-12-12)
When pH-sensitive molecules are incorporated into liposomes, drugs can be specifically released from these vesicles by a change of pH in the ambient serum. Liposomes containing the pH-sensitive lipid palmitoyl homocysteine (PHC) were constructed so that the greatest pH differential
Formation strategies, mechanism of intracellular delivery and potential clinical applications of pH-sensitive liposomes
Liu X and Huang G
Asian Journal of Pharmaceutical Sciences , 8(6), 319-328 (2013)
J Connor et al.
The Journal of cell biology, 101(2), 582-589 (1985-08-01)
We previously showed that liposomes composed of dioleoylphosphatidyl-ethanolamine and palmitoyl-homocysteine (8:2) are highly fusion competent when exposed to an acidic environment of pH less than 6.5. (Connor, J., M. B. Yatvin, and L. Huang, 1984, Proc. Natl. Acad. Sci. USA.
J Connor et al.
Proceedings of the National Academy of Sciences of the United States of America, 81(6), 1715-1718 (1984-03-01)
Sonicated unilamellar liposomes containing phosphatidylethanolamine and palmitoylhomocysteine fuse rapidly when the medium pH is lowered from 7 to 5. Liposome fusion was demonstrated by (i) mixing of the liposomal lipids as shown by resonance energy transfer, (ii) gel filtration, and
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