DPPG sodium | CAS# 200880-41-7 | lipid bilayers

MedKoo Cat#: 471171 | Name: DPPG sodium

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

DPPG has been used in many FDA approved liposomal drug formulations. It is an anionic phospholipid derivative. It has been used as a membrane stabilizer in several slow release, multivesicular liposomal formulations of Exparel®, Depocyt® and DepoDur®, for bupivacaine , cytyarabine and morphine. DDPG was found to promote transdermal drug delivery by Sakdiset P., et al. In a preclinic study, Negatively-charged DPPC-DPPG liposomes were found to have a significantly improved encapsulation rate, a low initial burst release and the slowest ocular release rate for ranibizumab.

Chemical Structure

DPPG sodium

CAS#200880-41-7 (sodium)

Theoretical Analysis

MedKoo Cat#: 471171

Name: DPPG sodium

CAS#: 200880-41-7 (sodium)

Chemical Formula: C38H74NaO10P

Exact Mass: 0.0000

Molecular Weight: 744.96

Elemental Analysis: C, 61.27; H, 10.01; Na, 3.09; O, 21.48; P, 4.16

Price and Availability

Size	Price	Availability
100mg	USD 250.00	2 Weeks
250mg	USD 450.00	2 Weeks
500g	USD 750.00	2 Weeks
1g	USD 1,250.00	2 Weeks

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Related CAS #

185463-23-4 (free acid) 200880-41-7 (sodium) 67232-81-9 (racemic sodium)

Synonym

DPPG sodium; DPPG-Na; MG-6060LS; MG6060LS; MG 6060LS; 1,2-DPPG; 16:0/16:0-PG; PG(16:0/16:0)

IUPAC/Chemical Name

sodium;[(2R)-2,3-di(hexadecanoyloxy)propyl] 2,3-dihydroxypropyl phosphate

InChi Key

LDWIWSHBGAIIMV-ODZMYOIVSA-M

InChi Code

InChI=1S/C38H75O10P.Na/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-37(41)45-33-36(34-47-49(43,44)46-32-35(40)31-39)48-38(42)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2;/h35-36,39-40H,3-34H2,1-2H3,(H,43,44);/q;+1/p-1/t35?,36-;/m1./s1

SMILES Code

O=P(OC[C@H](OC(CCCCCCCCCCCCCCC)=O)COC(CCCCCCCCCCCCCCC)=O)(OCC(O)CO)[O-].[Na+]

Appearance

Solid powder

Purity

>96% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

[P. Sakdiset, A. Okada, H. Todo, K. Sugibayashi, Selection of phospholipids to design liposome preparations with high skin penetration-enhancing effects, J. Drug Deliv. Sci. Technol. 44 (2018) 58–64, https://doi.org/10.1016/j.jddst.2017.11.021] [Joseph, R.R., Tan, D.W.N., Ramon, M.R.M. et al. Characterization of liposomal carriers for the trans-scleral transport of Ranibizumab. Sci Rep 7, 16803 (2017). https://doi.org/10.1038/s41598-017-16791-7]

Product Data

Product Data

Instruction

View handling instruction

Biological target:

DPPG sodium is used in the generation of micelles, liposomes and other types of artificial membranes.

In vitro activity:

To understand the interaction of A beta with lipid membranes, this study has examined A beta 40 with anionic dipalmitoylphosphatidylglycerol (DPPG), zwitterionic dipalmitoylphosphatidylcholine (DPPC), and cationic dipalmitoyltrimethylammonium propane (DPTAP) monolayers under different subphase conditions. This study have used a constant surface pressure insertion assay to assess the degree of peptide insertion into the lipids. Simultaneously, this study monitored the surface morphology of the monolayers with fluorescence microscopy. This study has also performed dual-probe fluorescence measurements where both the peptide and lipid are tagged with chromophores. Isotherm measurements show that A beta inserts into both DPTAP and DPPG monolayers under physiologically relevant conditions. Reference: Biophys J. 2004 Sep;87(3):1732-40. https://pubmed.ncbi.nlm.nih.gov/15345552/

In vivo activity:

Hyperthermia (HT) triggered drug release from phosphatidylglycerol-based thermosensitive liposomes (DPPG2-TSL) might prevent surgical bladder removal and toxicity from systemic chemotherapy. Treatment with DPPG2-TSL-DOX combined with intravesical HT outperformed systemic and intravesical DOX in vivo in rats. There might be a role for DPPG2-TSL encapsulating chemotherapeutics in the treatment of MIBC in the future. Reference: Int J Hyperthermia. 2021;38(1):1415-1424. https://pubmed.ncbi.nlm.nih.gov/34581259/

	Solvent	mg/mL	mM
Solubility
	Chloroform	2.0	2.68

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 744.96 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Alp G, Oztas Y. Facile L-Glutamine delivery to erythrocytes via DOPC-DPPG mixed liposomes. J Liposome Res. 2021 Dec;31(4):409-419. doi: 10.1080/08982104.2021.1918152. Epub 2021 May 4. PMID: 33944651. 2. Ege C, Lee KY. Insertion of Alzheimer's A beta 40 peptide into lipid monolayers. Biophys J. 2004 Sep;87(3):1732-40. doi: 10.1529/biophysj.104.043265. PMID: 15345552; PMCID: PMC1304578. 3. Brummelhuis ISG, Simons M, Lindner LH, Kort S, de Jong S, Hossann M, Witjes JA, Oosterwijk E. DPPG2-based thermosensitive liposomes as drug delivery system for effective muscle-invasive bladder cancer treatment in vivo. Int J Hyperthermia. 2021;38(1):1415-1424. doi: 10.1080/02656736.2021.1983038. PMID: 34581259. 4. van Valenberg FJP, Brummelhuis ISG, Lindner LH, Kuhnle F, Wedmann B, Schweizer P, Hossann M, Witjes JA, Oosterwijk E. DPPG2-Based Thermosensitive Liposomes with Encapsulated Doxorubicin Combined with Hyperthermia Lead to Higher Doxorubicin Concentrations in the Bladder Compared to Conventional Application in Pigs: A Rationale for the Treatment of Muscle-Invasive Bladder Cancer. Int J Nanomedicine. 2021 Jan 7;16:75-88. doi: 10.2147/IJN.S280034. PMID: 33447028; PMCID: PMC7802347.

In vitro protocol:

In vivo protocol:

1. Brummelhuis ISG, Simons M, Lindner LH, Kort S, de Jong S, Hossann M, Witjes JA, Oosterwijk E. DPPG2-based thermosensitive liposomes as drug delivery system for effective muscle-invasive bladder cancer treatment in vivo. Int J Hyperthermia. 2021;38(1):1415-1424. doi: 10.1080/02656736.2021.1983038. PMID: 34581259. 2. van Valenberg FJP, Brummelhuis ISG, Lindner LH, Kuhnle F, Wedmann B, Schweizer P, Hossann M, Witjes JA, Oosterwijk E. DPPG2-Based Thermosensitive Liposomes with Encapsulated Doxorubicin Combined with Hyperthermia Lead to Higher Doxorubicin Concentrations in the Bladder Compared to Conventional Application in Pigs: A Rationale for the Treatment of Muscle-Invasive Bladder Cancer. Int J Nanomedicine. 2021 Jan 7;16:75-88. doi: 10.2147/IJN.S280034. PMID: 33447028; PMCID: PMC7802347.

1: Katsai OG, Ruban OA, Krasnopolskyi YM. Preparation and in-vivo evaluation of cytochrome-C-containing liposomes. Pharmazie. 2017 Dec 1;72(12):736-740. doi: 10.1691/ph.2017.7072. PMID: 29441958.