870320P
Avanti
N-palmitoyl homocysteine (PHC)
Avanti Polar Lipids 870320P, powder
Synonym(s):
N-palmitoyl homocysteine (ammonium salt)
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About This Item
Empirical Formula (Hill Notation):
C20H42N2O3S
CAS Number:
Molecular Weight:
390.62
UNSPSC Code:
12352211
NACRES:
NA.25
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form
powder
packaging
pkg of 1 × 25 mg (870320P-25mg)
manufacturer/tradename
Avanti Polar Lipids 870320P
shipped in
dry ice
storage temp.
−20°C
SMILES string
[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
InChI key
WUXWCXRWTBPUKZ-UHFFFAOYSA-N
General description
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).
Biochem/physiol Actions
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.
Packaging
5 mL Amber Glass Screw Cap Vial (870320P-25mg)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Certificates of Analysis (COA)
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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)
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
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
Kayla Miller et al.
Nanomedicine (London, England), 11(6), 581-595 (2016-03-24)
Glioblastoma multiforme is a devastating disease with no curative options due to the difficulty in achieving sufficient quantities of effective chemotherapies into the tumor past the blood-brain barrier. Micelles loaded with temozolomide (TMZ) were designed to increase the delivery of
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