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MedKoo Cat#: 574259 | Name: MHAPC-Chol
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Description:

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

MHAPC-Chol is a cationic cholesterol. MHAPC-Chol, as part of a lipoplex with DOPE, has been used for siRNA delivery and gene silencing in MCF-7 cells in a luciferase assay without affecting cell viability. It has also been used to deliver siRNA into mice via intravenous injection, resulting in MHAPC-chol accumulation in the liver.

Chemical Structure

MHAPC-Chol
MHAPC-Chol
CAS#1027801-74-6

Theoretical Analysis

MedKoo Cat#: 574259

Name: MHAPC-Chol

CAS#: 1027801-74-6

Chemical Formula: C34H60N2O3

Exact Mass: 544.4604

Molecular Weight: 544.87

Elemental Analysis: C, 74.95; H, 11.10; N, 5.14; O, 8.81

Price and Availability

Size Price Availability Quantity
5mg USD 550.00 2 Weeks
10mg USD 900.00 2 Weeks
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Related CAS #
No Data
Synonym
MHAPC-Chol
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 (3-((2-hydroxyethyl)(methyl)amino)propyl)carbamate
InChi Key
XNSUBQXPLPQEHC-DYQRUOQXSA-N
InChi Code
InChI=1S/C34H60N2O3/c1-24(2)9-7-10-25(3)29-13-14-30-28-12-11-26-23-27(39-32(38)35-19-8-20-36(6)21-22-37)15-17-33(26,4)31(28)16-18-34(29,30)5/h11,24-25,27-31,37H,7-10,12-23H2,1-6H3,(H,35,38)/t25-,27+,28+,29-,30+,31+,33+,34-/m1/s1
SMILES Code
C[C@H](CCCC(C)C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](OC(NCCCN(C)CCO)=O)CC[C@]4(C)[C@@]3([H])CC[C@@]21C
Appearance
Solid powder
Purity
>95% (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
>3 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
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#C21M06C27
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
MHAPC-Chol is a cationic cholesterol.
In vitro activity:
Compared to OH-Chol-lipoplexes, the higher cellular association of MHAPC-lipoplexes correlated with the significantly higher zeta potentials, lower surface pH levels and "drier" surface, as evaluated by the generalized polarization of laurdan. EL-A hydrated the liposomal surface of MHAPC-lipoplexes but dehydrated that of OH-Chol-lipoplexes, while Tween 80 hydrated those of MHAPC- and OH-Chol-lipoplexes. In all, cationic liposomes composed of lipids with secondary and tertiary amine exhibited different surface properties and cellular associations of lipoplexes, and modification with surfactants further enlarged their difference. Reference: Chem Pharm Bull (Tokyo). 2009 Feb;57(2):138-43. https://pubmed.ncbi.nlm.nih.gov/19182402/
In vivo activity:
Transfection by liposomes with N,N-methyl hydroxyethyl aminopropane carbamoyl cholesterol iodide (MHAPC) showed the highest luciferase activity, resulting in 2- and 60-fold higher gene expression than jet-PEI and naked DNA, respectively. All the lipoplexes led to higher TNF-alpha levels in the lung compared to the nanoplex and jet-PEI, but our findings suggested that modification of the cationic cholesterol with a hydroxyethyl group at the tertiary amine terminal, MHAPC, promoted gene expression in the mouse lung without increasing the toxicity compared with other CCDs. Reference: Int J Pharm. 2008 Apr 16;354(1-2):196-203. https://pubmed.ncbi.nlm.nih.gov/18155371/
Solvent mg/mL mM comments
Solubility
Ethanol:PBS (pH 7.2) (1:6) 0.1 0.26
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 544.87 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.

Recalculate based on batch purity %
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. Ding W, Hattori Y, Qi X, Kitamoto D, Maitani Y. Surface properties of lipoplexes modified with mannosylerythritol lipid-a and tween 80 and their cellular association. Chem Pharm Bull (Tokyo). 2009 Feb;57(2):138-43. doi: 10.1248/cpb.57.138. PMID: 19182402. 2. Ding W, Izumisawa T, Hattori Y, Qi X, Kitamoto D, Maitani Y. Non-ionic surfactant modified cationic liposomes mediated gene transfection in vitro and in the mouse lung. Biol Pharm Bull. 2009 Feb;32(2):311-5. doi: 10.1248/bpb.32.311. PMID: 19182397. 3. Ding W, Izumisawa T, Hattori Y, Qi X, Kitamoto D, Maitani Y. Non-ionic surfactant modified cationic liposomes mediated gene transfection in vitro and in the mouse lung. Biol Pharm Bull. 2009 Feb;32(2):311-5. doi: 10.1248/bpb.32.311. PMID: 19182397.
In vitro protocol:
1. Ding W, Hattori Y, Qi X, Kitamoto D, Maitani Y. Surface properties of lipoplexes modified with mannosylerythritol lipid-a and tween 80 and their cellular association. Chem Pharm Bull (Tokyo). 2009 Feb;57(2):138-43. doi: 10.1248/cpb.57.138. PMID: 19182402. 2. Ding W, Izumisawa T, Hattori Y, Qi X, Kitamoto D, Maitani Y. Non-ionic surfactant modified cationic liposomes mediated gene transfection in vitro and in the mouse lung. Biol Pharm Bull. 2009 Feb;32(2):311-5. doi: 10.1248/bpb.32.311. PMID: 19182397.
In vivo protocol:
1. Ding W, Izumisawa T, Hattori Y, Qi X, Kitamoto D, Maitani Y. Non-ionic surfactant modified cationic liposomes mediated gene transfection in vitro and in the mouse lung. Biol Pharm Bull. 2009 Feb;32(2):311-5. doi: 10.1248/bpb.32.311. PMID: 19182397. 2. Ding W, Hattori Y, Higashiyama K, Maitani Y. Hydroxyethylated cationic cholesterol derivatives in liposome vectors promote gene expression in the lung. Int J Pharm. 2008 Apr 16;354(1-2):196-203. doi: 10.1016/j.ijpharm.2007.10.051. Epub 2007 Nov 9. PMID: 18155371.
1. Hattori, Y., Nakamura, M., Takeuchi, N., et al. Effect of cationic lipid in cationic liposomes on siRNA delivery into the lung by intravenous injection of cationic lipoplex. J. Drug. Target 27(2), 217-227 (2019).