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870320P

Avanti

N-palmitoyl homocysteine (PHC)

Avanti Research - A Croda Brand 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

form

powder

packaging

pkg of 1 × 25 mg (870320P-25mg)

manufacturer/tradename

Avanti Research - A Croda Brand 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)
Y Lee et al.
Wiley interdisciplinary reviews. Nanomedicine and nanobiotechnology, 9(5) (2017-02-16)
The ultimate goal of drug delivery is to increase the bioavailability and reduce the toxic side effects of the active pharmaceutical ingredient (API) by releasing them at a specific site of action. In the case of antitumor therapy, association of
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
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.

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