A phospholipid-porphyrin conjugate
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1-Palmitoyl-2-Pyropheophorbide a-sn-glycero-3-PC

Item No. 38430

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(7R)-7-[3-[(3S,4S)-9-ethenyl-14-ethyl-4,8,13,18-tetramethyl-20-phorbinyl]-1-oxopropoxy]-4-hydroxy-N,N,N-trimethyl-10-oxo-3,5,9-trioxa-4-phosphapentacosan-1-aminium, 4-oxide, inner salt
CAS Number
1287795-07-6
Synonyms
  • 1-Palmitoyl-2-Pyropheophorbide a-sn-glycero-3-Phosphocholine
  • 1-Palmitoyl-2-Pyropheophorbide a-sn-glycero-3-Phosphatidylcholine
  • Porphyrin-lipid
  • Pyro-PtdCho
Molecular Formula
C57H82N5O9P
Formula Weight
1012.3
Purity
≥90%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 1 mg/mlDMSO: 1 mg/mlEthanol: 1 mg/ml
SMILES
CC1=C(/C=C2C(CC)=C3C)NC(/C(C4)=C(N=C(/C=C(C(C)=C/5C=C)\NC5=C/C3=N/2)[C@H]6C)/[C@H]6CCC(O[C@H](COC(CCCCCCCCCCCCCCC)=O)CO[P]([O-])(OCC[N+](C)(C)C)=O)=O)=C1C4=O
InChi Code
InChI=1S/C57H82N5O9P/c1-11-14-15-16-17-18-19-20-21-22-23-24-25-26-53(64)68-35-41(36-70-72(66,67)69-30-29-62(8,9)10)71-54(65)28-27-44-39(6)48-32-46-37(4)42(12-2)50(58-46)33-47-38(5)43(13-3)51(59-47)34-49-40(7)55-52(63)31-45(56(44)60-48)57(55)61-49/h12,32-34,39,41,44H,2,11,13-31,35-36H2,1,3-10H3,(H2-,58,59,60,61,63,66,67)/t39-,41+,44-/m0/s1
InChi Key
JNOZUNXGSWKOPZ-WXDPHDKQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $83

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    5 mg

    $392

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    10 mg

    $743

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    Cayman Chemical
    Learn More About Leveraging Helper Lipids to Achieve Versatile LNPs
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    Product Description

    1-Palmitoyl-2-pyropheophorbide a-sn-glycero-3-PC is a phospholipid-porphyrin conjugate that is composed of phosphatidylcholine containing palmitic acid (Item No. 10006627) at the sn-1 position and the photosensitizer pyropheophorbide a (Item No. 21371) at the sn-2 position.1 Lipid nanoparticles (LNPs) containing 1-palmitoyl-2-pyropheophorbide a-sn-glycero-3-PC and encapsulating FAM-labeled siRNA are dissociated under irradiation with near-infrared light (NIR) in PC3-Luc6 cells. 1-Palmitoyl-2-pyropheophorbide a-sn-glycero-3-PC then enters the endolysosomal membrane and generates reactive oxygen species (ROS), which disrupt the membrane and allow the release of FAM-labeled siRNA into the cytosol. 1-Palmitoyl-2-pyropheophorbide a-sn-glycero-3-PC-stabilized nanoemulsions loaded with the mitotic inhibitor paclitaxel (Item No. 10461), combined with laser irradiation, reduce tumor growth and increase survival in a KB squamous cell carcinoma mouse xenograft model.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Mo, Y., Cheng, M.H.Y., D'Elia, A., et al. Light-activated siRNA endosomal release (LASER) by porphyrin lipid nanoparticles. ACS Nano 17(5), 4688-4703 (2023).

    2. Chang, E., Bu, J., Ding, L., et al. Porphyrin-lipid stabilized paclitaxel nanoemulsion for combined photodynamic therapy and chemotherapy. J. Nanobiotechnology 19(1), 154 (2021).