A glucosamine-based lipid conjugate
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Glucosamine Cholesterol

Item No. 39446

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[[4-[(3β)-cholest-5-en-3-yloxy]-1,4-dioxobutyl]amino]-2-deoxy-D-glucopyranose
CAS Number
1257309-90-2
Molecular Formula
C37H61NO8
Formula Weight
647.9
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble (sonicate)
SMILES
C[C@]12CC[C@H](OC(CCC(N[C@H]3C(O)O[C@H](CO)[C@@H](O)[C@@H]3O)=O)=O)CC1=CC[C@]4([H])[C@]2([H])CC[C@@]5(C)[C@@]4([H])CC[C@]5([H])[C@@H](CCCC(C)C)C
InChi Code
InChI=1S/C37H61NO8/c1-21(2)7-6-8-22(3)26-11-12-27-25-10-9-23-19-24(15-17-36(23,4)28(25)16-18-37(26,27)5)45-31(41)14-13-30(40)38-32-34(43)33(42)29(20-39)46-35(32)44/h9,21-22,24-29,32-35,39,42-44H,6-8,10-20H2,1-5H3,(H,38,40)/t22-,24+,25+,26-,27+,28+,29-,32-,33-,34-,35?,36+,37-/m1/s1
InChi Key
CEZJGMHPGUGAEW-ACSCFQKYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $72

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    5 mg

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    10 mg

    $429

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    Cayman Chemical
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    Product Description

    Glucosamine cholesterol is a glucosamine-based lipid conjugate that has been used in the formation of lipid nanoparticles (LNPs).1 It forms a stable, ordered bilayer with the glucosamine moiety facing outward to facilitate recognition by glucose transporter 1 (GLUT1) on cells. LNPs containing glucosamine cholesterol and encapsulating ceramide induce apoptosis in hypoxic human A549 lung carcinoma cells and A549-derived side population cells, also known as cancer stem cells (CSCs), but not hypoxic mouse L-929 fibroblasts. LNPs containing glucosamine cholesterol and encapsulating paclitaxel (Item No. 10461) and carboplatin (Item No. 13112) reduce tumor volume and increase the number of tumor-associated cytotoxic T cells in an LL/2 murine lung carcinoma model.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yu, L.-Y., Shueng, P.-W., Chiu, H.-C., et al. Glucose transporter 1-mediated transcytosis of glucosamine-labeled liposomal ceramide targets hypoxia niches and cancer stem cells to enhance therapeutic efficacy. ACS Nano 17(14), 13158-13175 (2023).