880123 | DSPE-PEG(5000) Folate

1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-[folate(polyethylene glycol)-5000] (ammonium salt)

DSPE-PEG(5000) Folate

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Info

DSPE-PEG(5000) Folate

1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-[folate(polyethylene glycol)-5000] (ammonium salt)

Folate receptors are cellular surface markers for numerous solid tumors and myeloid leukemias. Avanti now offers a derivative, DSPE-PEG-folate, which can be incorporated into liposomes as a targeting ligand.
Folate targeted drug delivery has emerged as an alternative therapy for the treatment and imaging of many cancers and inflammatory diseases. Due to its small molecular size and high binding affinity for cell surface folate receptors (FR), folate conjugates have the ability to deliver a variety of molecular complexes to pathologic cells without causing harm to normal tissues. Complexes that have been successfully delivered to FR expressing cells, to date, include protein toxins, immune stimulants, chemotherapeutic agents, liposomes, nanoparticles, and imaging agents. This review will summarize the applications of folic acid as a targeting ligand and highlight the various methods being developed for delivery of therapeutic and imaging agents to FR-expressing cells.
Hilgenbrink, A.R., Low, P.S. (2005). Folate Receptor-Mediated Drug Targeting: From Therapeutics to Diagnostics. Wiley-Liss, Inc. and the American Pharmacists Association J Pharm Sci 94:2135–2146.

Representative Structure

The molecular weight and exact mass are averages based on the polydispersity of PEG.

Data
Hygroscopic
Yes
Light Sensitive
No
Molecular Formula

C287H558N11O127P (average MW due to polydispersity of PEG)

Percent Composition

C 55.36%, H 9.03%, N 2.47%, O 32.63%, P 0.50%

Purity
According to the published synthetic protocol, the product will be 80-85% gamma conjugated and contain 15-20% of the other positional isomer. This does not seem to impact the functionality.
Stability
1 Years
Storage Temperature
-20°C
CAS Number
1236288-25-7
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
6226.545
Exact Mass
6222.728
Synonyms
1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-[carbonyl-amino(polyethylene glycol)-5000-N’-(folyl)] (ammonium salt)
References

Yoon HY, Yang HM, Kim CH, Goo YT, Hwang GY, Chang IH, Whang YM, Choi YW. Enhanced Intracellular Delivery of BCG Cell Wall Skeleton into Bladder Cancer Cells Using Liposomes Functionalized with Folic Acid and Pep-1 Peptide. Pharmaceutics. 2019 Dec 4;11(12):E652. doi: 10.3390/pharmaceutics11120652. PMID: 31817179.

PubMed ID: 31817179

Yang Z, Xu J, Zong S, Xu S, Zhu D, Zhang Y, Chen C, Wang C, Wang Z, Cui Y. Lead Halide Perovskite Nanocrystals-Phospholipid Micelles and Their Biological Applications: Multiplex Cellular Imaging and in Vitro Tumor Targeting. ACS Appl Mater Interfaces. 2019 Dec 26;11(51):47671-47679. doi: 10.1021/acsami.9b12924. Epub 2019 Oct 30.

PubMed ID: 3163335

Akhtar A, Ghali L, Wang SX, Bell C, Li D, Wen X. Optimisation of Folate-Mediated Liposomal Encapsulated Arsenic Trioxide for Treating HPV-Positive Cervical Cancer Cells In Vitro. Int J Mol Sci. 2019 Apr 30;20(9). pii: E2156. doi: 10.3390/ijms20092156.

PubMed ID: 31052347

Nassir AM, Ibrahim IAA, Md S, Waris M, Tanuja, Ain MR, Ahmad I, Shahzad N. Surface functionalized folate targeted oleuropein nano-liposomes for prostate tumor targeting: Invitro and invivo activity. Life Sci. 2019 Mar 1;220:136-146. doi: 10.1016/j.lfs.2019.01.053. Epub 2019 Jan 31.

PubMed ID: 30710640

Chiu SJ, Liu S, Perrotti D, Marcucci G, Lee RJ. Efficient delivery of a Bcl-2-specific antisense oligodeoxyribonucleotide (G3139) via transferrin receptor-targeted liposomes. J Control Release. 2006 May 15;112(2):199-207. Epub 2006 Mar 6.

PubMed ID: 16564596

Wu J, Liu Q, Lee RJ. A folate receptor-targeted liposomal formulation for paclitaxel. Int J Pharm. 2006 Jun 19;316(1-2):148-53. Epub 2006 Mar 6.

PubMed ID: 16564654

Shiokawa T, Hattori Y, Kawano K, Ohguchi Y, Kawakami H, Toma K, Maitani Y. Effect of polyethylene glycol linker chain length of folate-linked microemulsions loading aclacinomycin A on targeting ability and antitumor effect in vitro and in vivo. Clin Cancer Res. 2005 Mar 1;11(5):2018-25.

PubMed ID: 15756028

Zhang Y, Guo L, Roeske RW, Antony AC, Jayaram HN. Pteroyl-gamma-glutamate-cysteine synthesis and its application in folate receptor-mediated cancer cell targeting using folate-tethered liposomes. Anal Biochem. 2004 Sep 1;332(1):168-77.

PubMed ID: 15301962

Gabizon A, Horowitz AT, Goren D, Tzemach D, Mandelbaum-Shavit F, Qazen MM, Zalipsky S. Targeting folate receptor with folate linked to extremities of poly(ethylene glycol)-grafted liposomes: in vitro studies. Bioconjug Chem. 1999 Mar-Apr;10(2):289-98.

PubMed ID: 10077479
Certificates of Analysis

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