DC-Cholesterol HCl | CAS# 166023-21-8 | nucleic acids and drug therapies

MedKoo Cat#: 414888 | Name: DC-Cholesterol HCl

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Description:

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

DC-Chol (hydrochloride) has been shown to have potential as a nanocarrier for nucleic acids and drug therapies. DC-cholesterol is a derivative of cholesterol with a quarternary amine salt attached via the 3-C position. DC-cholesterol can be combined with DOPE (850725) to produce powerful liposomes. DC-Chol (hydrochloride) is a derivative of cholesterol with a tertiary amine group. DC-cholesterol can be combined with DOPE (850725) to form cationic liposomes that can be used as intracellular delivery nanocarrier for nucleic acids.

Chemical Structure

DC-Cholesterol HCl

CAS#166023-21-8 (HCl)

Theoretical Analysis

MedKoo Cat#: 414888

Name: DC-Cholesterol HCl

CAS#: 166023-21-8 (HCl)

Chemical Formula: C32H57ClN2O2

Exact Mass: 536.4109

Molecular Weight: 537.27

Elemental Analysis: C, 71.54; H, 10.69; Cl, 6.60; N, 5.21; O, 5.96

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 450.00	2 Weeks
250mg	USD 750.00	2 Weeks

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Related CAS #

137056-72-5 (free base) 166023-21-8 (HCl)

Synonym

DC-Chol hydrochloride; DC-Chol HCl; Cholesteryl 3β-N-(dimethylaminoethyl)carbamate; DC-Cholesterol HCl;

IUPAC/Chemical Name

(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl (2-(dimethylamino)ethyl)carbamate hydrochloride

InChi Key

ISXSJGHXHUZXNF-LXZPIJOJSA-N

InChi Code

InChI=1S/C32H56N2O2.ClH/c1-22(2)9-8-10-23(3)27-13-14-28-26-12-11-24-21-25(36-30(35)33-19-20-34(6)7)15-17-31(24,4)29(26)16-18-32(27,28)5;/h11,22-23,25-29H,8-10,12-21H2,1-7H3,(H,33,35);1H/t23-,25+,26+,27-,28+,29+,31+,32-;/m1./s1

SMILES Code

CC(CCC[C@H]([C@]1(CC[C@]2([C@@]3(CC=C4C[C@H](CC[C@@]4([C@]3(CC[C@@]21C)[H])C)OC(NCCN(C)C)=O)[H])[H])[H])C)C.Cl

Appearance

Solid powder

Purity

>97% (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

DC-chol/DOPE is the first cationic liposome formulation used in human clinical trial. DC-cholesterol has also been shown by researcher at Merck as an adjuvant to boost immune response for synthetic vaccines. [Gao X, Huang L. A novel cationic liposome reagent for efficient transfection of mammalian cells. Biochem Biophys Res Commun. 1991;179(1):280–5] [G. Nabel, E. Nabel, Z. Yang, B. Fox, G. Plautz , X. Gao, L. Huang, S. Shu, D. Gordon, A. Chang Direct gene transfer with DNA-liposome complexes in melanoma: expression, biologic activity, and lack of toxicity in humans. Proceedings of the National Academy of Sciences of the United States of America,1993 90(23):11307-11 ] [Brunel, F., Darbouret, A. and Ronco, J. (1999) Cationic lipid DC Chol induces an improved and balanced immunity able to overcome the unresponsiveness to the Hepatitis B vaccine. Vaccine 17:2192-2203 ]

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 537.27 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

1: Muñoz-Ubeda M, Rodríguez-Pulido A, Nogales A, Martín-Molina A, Aicart E, Junquera E. Effect of lipid composition on the structure and theoretical phase diagrams of DC-Chol/DOPE-DNA lipoplexes. Biomacromolecules. 2010 Dec 13;11(12):3332-40. doi: 10.1021/bm1008124. Epub 2010 Nov 8. PMID: 21058732. 2: Chang SF, Yeh CC, Chen PJ, Chang HI. The Impact of Lipid Types and Liposomal Formulations on Osteoblast Adiposity and Mineralization. Molecules. 2018 Jan 2;23(1):95. doi: 10.3390/molecules23010095. PMID: 29301300; PMCID: PMC6017718. 3: Rodríguez-Pulido A, Ortega F, Llorca O, Aicart E, Junquera E. A physicochemical characterization of the interaction between DC-Chol/DOPE cationic liposomes and DNA. J Phys Chem B. 2008 Oct 2;112(39):12555-65. doi: 10.1021/jp804066t. Epub 2008 Aug 27. PMID: 18729499. 4: Kodama Y, Harauchi S, Kawanabe S, Ichikawa N, Nakagawa H, Muro T, Higuchi N, Nakamura T, Kitahara T, Sasaki H. Safe and effective delivery of small interfering RNA with polymer- and liposomes-based complexes. Biol Pharm Bull. 2013;36(6):995-1001. doi: 10.1248/bpb.b13-00054. PMID: 23727920. 5: Ho EA, Ramsay E, Ginj M, Anantha M, Bregman I, Sy J, Woo J, Osooly-Talesh M, Yapp DT, Bally MB. Characterization of cationic liposome formulations designed to exhibit extended plasma residence times and tumor vasculature targeting properties. J Pharm Sci. 2010 Jun;99(6):2839-53. doi: 10.1002/jps.22043. PMID: 20091826. 6: Colonna C, Conti B, Genta I, Alpar OH. Non-viral dried powders for respiratory gene delivery prepared by cationic and chitosan loaded liposomes. Int J Pharm. 2008 Nov 19;364(1):108-18. doi: 10.1016/j.ijpharm.2008.07.034. Epub 2008 Aug 19. PMID: 18775770. 7: Hafez IM, Ansell S, Cullis PR. Tunable pH-sensitive liposomes composed of mixtures of cationic and anionic lipids. Biophys J. 2000 Sep;79(3):1438-46. doi: 10.1016/S0006-3495(00)76395-8. PMID: 10969005; PMCID: PMC1301037. 8: Suga K, Akizaki K, Umakoshi H. Quantitative Monitoring of Microphase Separation Behaviors in Cationic Liposomes Using HHC, DPH, and Laurdan: Estimation of the Local Electrostatic Potentials in Microdomains. Langmuir. 2016 Apr 19;32(15):3630-6. doi: 10.1021/acs.langmuir.5b04682. Epub 2016 Apr 6. PMID: 27022833. 9: Gonçalves C, Berchel M, Gosselin MP, Malard V, Cheradame H, Jaffrès PA, Guégan P, Pichon C, Midoux P. Lipopolyplexes comprising imidazole/imidazolium lipophosphoramidate, histidinylated polyethyleneimine and siRNA as efficient formulation for siRNA transfection. Int J Pharm. 2014 Jan 2;460(1-2):264-72. doi: 10.1016/j.ijpharm.2013.11.005. Epub 2013 Nov 10. PMID: 24225347. 10: Sakaguchi N, Kojima C, Harada A, Koiwai K, Shimizu K, Emi N, Kono K. Generation of highly potent nonviral gene vectors by complexation of lipoplexes and transferrin-bearing fusogenic polymer-modified liposomes in aqueous glucose solution. Biomaterials. 2008 Mar;29(9):1262-72. doi: 10.1016/j.biomaterials.2007.11.016. PMID: 18076985.