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Merck
CN

934569

NanoFabTx™ Photoactivatable Lipid

redAzoPC

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About This Item

Empirical Formula (Hill Notation):
C46H72Cl4N3O8P
CAS Number:
2839130-47-9
Molecular Weight:
967.86
UNSPSC Code:
12161503
NACRES:
NA.21

Key Documents

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Product Name

NanoFabTx™ Photoactivatable Lipid, redAzoPC

InChI

1S/C46H72Cl4N3O8P/c1-6-8-10-11-12-13-14-15-16-17-18-19-20-21-22-26-43(54)58-34-38(35-60-62(56,57)59-29-28-53(3,4)5)61-44(55)27-23-25-37-32-41(49)46(42(50)33-37)52-51-45-39(47)30-36(24-9-7-2)31-40(45)48/h30-33,38H,6-29,34-35H2,1-5H3/b52-51+/t38-/m1/s1

InChI key

FLGJQVLXMDITOI-MYZMGNDKSA-N

SMILES string

[O-]P(OCC[N+](C)(C)C)(OC[C@H](OC(CCCC1=CC(Cl)=C(C(Cl)=C1)/N=N/C2=C(C=C(C=C2Cl)CCCC)Cl)=O)COC(CCCCCCCCCCCCCCCCC)=O)=O

assay

≥90%

form

solid

color

orange to dark red

storage temp.

−20°C

Quality Level

100

Application

Lipid nanoparticle and liposome drug delivery systems

Features and Benefits

  • Similar drug loading, encapsulation efficiency, size, and polydispersity to non-photoswitchable lipids
  • Light-induced drug delivery
  • Targeted and controlled release
  • Overcomes limitations associated to UV-switchable lipids

General description

The NanoFabTx Photoactivatable Lipid, redAzoPC is a red-light photoswitchable lipid for controlled and targeted drug delivery. The tetra-ortho-chloro-azobenzene of redAzoPC can be isomerized from the cis to the trans conformation at 660 nm light. LNPs prepared using the NanoFabTx™ Photoactivatable Lipid, redAzoPC result in controlled drug release following deep red light irradiation.

Legal Information

NANOFABTX is a trademark of Sigma-Aldrich Co. LLC

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000288724
0000246414
0000246414
0000288724

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Nisha Chander et al.
Small (Weinheim an der Bergstrasse, Germany), 17(21), e2008198-e2008198 (2021-04-22)
Encapsulation of small molecule drugs in long-circulating lipid nanoparticles (LNPs) can reduce toxic side effects and enhance accumulation at tumor sites. A fundamental problem, however, is the slow release of encapsulated drugs from these liposomal systems at the disease site
Tufan K Mukhopadhyay et al.
Current opinion in pharmacology, 63, 102202-102202 (2022-03-13)
Many aspects of cell signaling are controlled by lipids. Several signaling lipids have been functionalized with an azobenzene photoswitch to control underlying signaling dynamics with light. Herein, we provide an overview of signaling photolipids developed to date focusing on their
Johannes Morstein et al.
Chembiochem : a European journal of chemical biology, 22(1), 73-83 (2020-08-14)
Photoswitchable lipids are emerging tools for the precise manipulation and study of lipid function. They can modulate many aspects of membrane biophysics, including permeability, fluidity, lipid mobility and domain formation. They are also very useful in lipid physiology and enable

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