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4004-05-1 Usage

Description

1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) is a neutral phospholipid that is sensitive to pH changes and is a synthetic analog of naturally-occurring phosphatidylethanolamine (PE) containing 18:1 fatty acids at the sn-1 and sn-2 positions. It is primarily formed in the reaction of CDP-ethanolamine and diacylglycerol and is a major component of cell membranes in bacteria and the nervous system. DOPE exists as a yellowish wax and has the ability to form various structures such as inverted hexagonal micelles and spherical micelles depending on the pH.

Uses

Used in Pharmaceutical Applications:
1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) is used as a component in the formation of heterogeneous liposomes with N-[1-(2,3-dioleoyloxy)propyl]-N,N,N-trimethylammonium methylsulfate (DOTAP). These liposomes serve as delivery vehicles for therapeutic agents, enhancing the efficiency of drug administration.
Used in Gene Delivery:
DOPE is used as an emulsifier to facilitate the transport of DNA-liposome complexes across membranes. It is often used in combination with cationic phospholipids to increase the efficiency of DNA transfection studies, providing a non-viral method of gene delivery.
Used in Biomedical Research:
DOPE has been utilized in the preparation of liposomes for various research applications, such as the reconstitution of human uncoupling protein 1 (UCP1) and the conjugation of Caenorhabditis elegans autophagy-related cysteine protease proteins. Additionally, it has been used in the generation of giant unilamellar vesicles (GUVs) for studying septin-induced deformation.
Used in the Preparation of Liposomes and Giant Unilamellar Vesicles (GUVs):
DOPE is employed in the preparation of liposomes and GUVs due to its ability to form different structures based on pH changes, making it a versatile component in the study of membrane biophysics and the development of novel drug delivery systems.

Biological Activity

DOPE in mixed membranes have been found to decrease fluorescence lifetime and increase acyl-chain order. DOPE is an essential component of cationic liposomes designed to deliver DNA into gliosarcoma and kidney cell lines (gene therapy).

Biochem/physiol Actions

DOPE in mixed membranes have been found to decrease fluorescence lifetime and increase acyl-chain order. DOPE is an essential component of cationic liposomes designed to deliver DNA into gliosarcoma and kidney cell lines (gene therapy).

Check Digit Verification of cas no

The CAS Registry Mumber 4004-05-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,0,0 and 4 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 4004-05:
(6*4)+(5*0)+(4*0)+(3*4)+(2*0)+(1*5)=41
41 % 10 = 1
So 4004-05-1 is a valid CAS Registry Number.
InChI:InChI=1/C41H78NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(43)47-37-39(38-49-51(45,46)48-36-35-42)50-41(44)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,39H,3-16,21-38,42H2,1-2H3,(H,45,46)/b19-17-,20-18-/t39-/m1/s1

4004-05-1 Well-known Company Product Price

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  • TCI America

  • (D4251)  1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine  >98.0%(T)

  • 4004-05-1

  • 250mg

  • 1,250.00CNY

  • Detail
  • Sigma

  • (76548)  1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine  ≥97.0% (TLC)

  • 4004-05-1

  • 76548-100MG

  • 1,826.37CNY

  • Detail
  • Sigma

  • (76548)  1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine  ≥97.0% (TLC)

  • 4004-05-1

  • 76548-1G

  • 7,330.05CNY

  • Detail
  • Sigma

  • (P1223)  L-α-Phosphatidylethanolamine,dioleoyl  ≥99% (GC), ≥98% (TLC), lyophilized powder

  • 4004-05-1

  • P1223-25MG

  • 1,299.87CNY

  • Detail
  • Sigma

  • (P1223)  L-α-Phosphatidylethanolamine,dioleoyl  ≥99% (GC), ≥98% (TLC), lyophilized powder

  • 4004-05-1

  • P1223-100MG

  • 3,931.20CNY

  • Detail
  • Sigma

  • (P1223)  L-α-Phosphatidylethanolamine,dioleoyl  ≥99% (GC), ≥98% (TLC), lyophilized powder

  • 4004-05-1

  • P1223-500MG

  • 15,408.90CNY

  • Detail
  • Sigma

  • (54008)  1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine  ≥98.0% (TLC)

  • 4004-05-1

  • 54008-25MG

  • 561.60CNY

  • Detail
  • Sigma

  • (54008)  1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine  ≥98.0% (TLC)

  • 4004-05-1

  • 54008-100MG

  • 1,697.67CNY

  • Detail
  • Sigma

  • (42490)  1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine  ≥99.0% (10 mg phospholipid per ml CHCl3, TLC)

  • 4004-05-1

  • 42490-2.5ML

  • 759.33CNY

  • Detail
  • Sigma

  • (42490)  1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine  ≥99.0% (10 mg phospholipid per ml CHCl3, TLC)

  • 4004-05-1

  • 42490-10ML

  • 2,467.53CNY

  • Detail

4004-05-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,2-DIOLEOYL-SN-GLYCERO-3-PHOSPHOETHANOLAMINE

1.2 Other means of identification

Product number -
Other names 1,2-dioleoyl-sn-glycero-3-phosphatidylethanolamine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:4004-05-1 SDS

4004-05-1Synthetic route

dioleoylphosphatidylcholine
4235-95-4

dioleoylphosphatidylcholine

ethanolamine
141-43-5

ethanolamine

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

Conditions
ConditionsYield
With PLD transesterification;90%
L-1,2-Di-O-oleoyl-glycerin-3-phosphorsaeurebenzylester-<2-triphenylmethylamino-ethylester>

L-1,2-Di-O-oleoyl-glycerin-3-phosphorsaeurebenzylester-<2-triphenylmethylamino-ethylester>

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

Conditions
ConditionsYield
(i) NaI, (ii) aq. AcOH; Multistep reaction;
1,2-dioleoyl-sn-glycerol
24529-88-2

1,2-dioleoyl-sn-glycerol

ethanolamine
141-43-5

ethanolamine

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

Conditions
ConditionsYield
With triethylamine; trichlorophosphate 1) THF, a) 0 deg C, 1 h, b) room temp., 3 h, 2) THF, a) 0 deg C, 4 h, b) room temp., 8 h; Yield given. Multistep reaction;
sodium-salt of phosphoric acid-<(R)-1,2-bis-oleoyloxy-propyl ester>-<2-phthalimido-ethyl ester>

sodium-salt of phosphoric acid-<(R)-1,2-bis-oleoyloxy-propyl ester>-<2-phthalimido-ethyl ester>

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

Conditions
ConditionsYield
With hydrazine hydrate
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 66 percent
2: 80 percent
3: 90 percent / PLD
View Scheme
1,2-dioleoyl-sn-glycero-3-phosphate sodium salt
108392-02-5

1,2-dioleoyl-sn-glycero-3-phosphate sodium salt

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent
2: 90 percent / PLD
View Scheme
(S)-3-(3,4-Dimethoxybenzyloxy)propane-1,2-diyl Dioleate
139115-88-1

(S)-3-(3,4-Dimethoxybenzyloxy)propane-1,2-diyl Dioleate

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 84 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / CH2Cl2; H2O / 2 h
2: 1) Et3N, POCl3, 2) Et3N / 1) THF, a) 0 deg C, 1 h, b) room temp., 3 h, 2) THF, a) 0 deg C, 4 h, b) room temp., 8 h
View Scheme
L-1,2-Di-O-oleoyl-glycerin-3-phosphorsaeure-dibenzylester
19805-13-1

L-1,2-Di-O-oleoyl-glycerin-3-phosphorsaeure-dibenzylester

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (i) NaI, (ii) AgNO3
2: benzene
3: (i) NaI, (ii) aq. AcOH
View Scheme
L-1,2-Di-O-oleoyl-glycerin-3-phosphorsaeurebenzylester-silbersalz

L-1,2-Di-O-oleoyl-glycerin-3-phosphorsaeurebenzylester-silbersalz

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: benzene
2: (i) NaI, (ii) aq. AcOH
View Scheme
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

3-propionic acid
80028-35-9

3-propionic acid

C50H88N3O9P

C50H88N3O9P

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; Inert atmosphere;100%
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

N2-[N2,N6-bis(tert-butoxycarbonyl)-L-lysyl]-N6-(tert-butoxycarbonyl)-L-lysine
45315-76-2

N2-[N2,N6-bis(tert-butoxycarbonyl)-L-lysyl]-N6-(tert-butoxycarbonyl)-L-lysine

C68H126N5O16P

C68H126N5O16P

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; Inert atmosphere;97%
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

N-hydroxysuccinimidyl ester 3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclo-hexa-1,4-dienyl) butanoic acid
121030-88-4

N-hydroxysuccinimidyl ester 3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclo-hexa-1,4-dienyl) butanoic acid

C55H94NO11P
1073588-75-6

C55H94NO11P

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; Inert atmosphere;96%
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

Propiolic acid
471-25-0

Propiolic acid

1,2-dioleoyl-sn-glycero-3-phosphoethanoloamine-N-prop-2'-ynamide
910227-37-1

1,2-dioleoyl-sn-glycero-3-phosphoethanoloamine-N-prop-2'-ynamide

Conditions
ConditionsYield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 40h;95%
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

hexanedioic acid bis(N-hydroxysuccinimide ester)
59156-70-6

hexanedioic acid bis(N-hydroxysuccinimide ester)

DOPE-Ad-ONSu
930280-91-4

DOPE-Ad-ONSu

Conditions
ConditionsYield
With triethylamine In chloroform; N,N-dimethyl-formamide at 20℃; for 2h;95%
In chloroform; N,N-dimethyl-formamide
In chloroform; N,N-dimethyl-formamide
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

3-(1-(1-(4-((6-amino-8-hydroxy-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)phenyl)-1-oxo-5,8,11,14,17,20,23,26,29,32-decaoxa-2-azatetratriacontan-34-yl)-1H-1,2,3-triazol-4-yl)propanoic acid
1149339-80-9

3-(1-(1-(4-((6-amino-8-hydroxy-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)phenyl)-1-oxo-5,8,11,14,17,20,23,26,29,32-decaoxa-2-azatetratriacontan-34-yl)-1H-1,2,3-triazol-4-yl)propanoic acid

2-(3-(1-(1-(4-((6-amino-8-hydroxy-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)phenyl)-1-oxo-5,8,11,14,17,20,23,26,29,32-decaoxa-2-azatetratriacontan-34-yl)-1H-1,2,3-triazole-4-yl)propanamido)ethyl 2,3-bis(oleoyloxy)propyl phosphate

2-(3-(1-(1-(4-((6-amino-8-hydroxy-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)phenyl)-1-oxo-5,8,11,14,17,20,23,26,29,32-decaoxa-2-azatetratriacontan-34-yl)-1H-1,2,3-triazole-4-yl)propanamido)ethyl 2,3-bis(oleoyloxy)propyl phosphate

Conditions
ConditionsYield
With 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃;92%
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

3-(2'-acetoxy-4',6'-dimethylphenyl)-3,3-dimethylpropanoic acid
134098-68-3

3-(2'-acetoxy-4',6'-dimethylphenyl)-3,3-dimethylpropanoic acid

C56H96NO11P

C56H96NO11P

Conditions
ConditionsYield
Stage #1: 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine; 3-(2'-acetoxy-4',6'-dimethylphenyl)-3,3-dimethylpropanoic acid With benzotriazol-1-ol In N,N-dimethyl-formamide at 0℃; for 0.0833333h; Inert atmosphere;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 5h; Inert atmosphere;
92%
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

4-{[6-amino-2-(2-methoxyethoxy)-8-oxo-7H-purine-9(8H)-yl]methyl}benzoic acid
1062444-54-5

4-{[6-amino-2-(2-methoxyethoxy)-8-oxo-7H-purine-9(8H)-yl]methyl}benzoic acid

(2R)‑3‑(((2‑(4‑((6‑amino‑2‑(2‑methoxyethoxy)‑8‑oxo‑7,8‑dihydro‑9H-purin‑9‑yl)methyl)benzamido)ethoxy)(hydroxy)phosphoryl)oxy)propane‑1,2‑diyldioleate

(2R)‑3‑(((2‑(4‑((6‑amino‑2‑(2‑methoxyethoxy)‑8‑oxo‑7,8‑dihydro‑9H-purin‑9‑yl)methyl)benzamido)ethoxy)(hydroxy)phosphoryl)oxy)propane‑1,2‑diyldioleate

Conditions
ConditionsYield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane; N,N-dimethyl-formamide79%
Stage #1: 4-{[6-amino-2-(2-methoxyethoxy)-8-oxo-7H-purine-9(8H)-yl]methyl}benzoic acid With triethylamine; HATU In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere;
Stage #2: 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine In dichloromethane; N,N-dimethyl-formamide for 12h; Solvent; Reagent/catalyst;
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

fluoresceinyl 5-isothiocyanate
1173-43-9

fluoresceinyl 5-isothiocyanate

C62H89N2O13PS

C62H89N2O13PS

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere;79%
3-(2-((bis(benzyloxy)phosphoryl)oxy)-4,6-dimethylphenyl)-3-methylbutanoic acid
153910-64-6

3-(2-((bis(benzyloxy)phosphoryl)oxy)-4,6-dimethylphenyl)-3-methylbutanoic acid

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

(2R)-3-(((2-(3-(2-((bis(benzyloxy)phosphoryl)oxy)-4,6-dimethylphenyl)-3-methylbutanamido)ethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl dioleate

(2R)-3-(((2-(3-(2-((bis(benzyloxy)phosphoryl)oxy)-4,6-dimethylphenyl)-3-methylbutanamido)ethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl dioleate

Conditions
ConditionsYield
Stage #1: 3-(2-((bis(benzyloxy)phosphoryl)oxy)-4,6-dimethylphenyl)-3-methylbutanoic acid; 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine With benzotriazol-1-ol In N,N-dimethyl-formamide at 0℃; for 0.0833333h;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide
77%
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

C16H17NO6
1073493-61-4

C16H17NO6

C53H90NO11P
1073588-74-5

C53H90NO11P

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; Inert atmosphere;75%
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

N-(tert-butoxycarbonyl)-4-aminobutanoic acid
57294-38-9

N-(tert-butoxycarbonyl)-4-aminobutanoic acid

C50H93N2O11P

C50H93N2O11P

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In chloroform; N,N-dimethyl-formamide at 20℃; Inert atmosphere;64%
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

5-(((2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl)oxy)-5-oxopentanoic acid
1415981-75-7

5-(((2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl)oxy)-5-oxopentanoic acid

(Z)-(2R)-3-(((2-(5-(((2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl)oxy)-5-oxopentanamido)ethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl dioleate
1415981-76-8

(Z)-(2R)-3-(((2-(5-(((2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl)oxy)-5-oxopentanamido)ethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl dioleate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In chloroform; N,N-dimethyl-formamide at 20℃; Inert atmosphere;61%
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

(1R,8S,9ξ)-bicyclo[6.1.0]non-4-yn-9-ylmethyl (4-nitrophenyl) carbonate

(1R,8S,9ξ)-bicyclo[6.1.0]non-4-yn-9-ylmethyl (4-nitrophenyl) carbonate

(2R)-3-(((2-(((((1R,8S,9s)-bicyclo[6.1.0]non-4-yn-9-yl)methoxy)carbonyl)amino)ethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl dioleate

(2R)-3-(((2-(((((1R,8S,9s)-bicyclo[6.1.0]non-4-yn-9-yl)methoxy)carbonyl)amino)ethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl dioleate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; N,N-dimethyl-formamide at 60℃; for 6h;60%
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

4-{[6-amino-2-(2-methoxyethoxy)-8-oxo-7H-purine-9(8H)-yl]methyl}benzoic acid
1062444-54-5

4-{[6-amino-2-(2-methoxyethoxy)-8-oxo-7H-purine-9(8H)-yl]methyl}benzoic acid

2-(4-((6-amino-2-(2-methoxyethoxy)-8-oxo-7H-purin-9(8H)-yl)methyl)benzamido)ethyl 2,3-bis(oleoyloxy)propyl phosphate
1346265-99-3

2-(4-((6-amino-2-(2-methoxyethoxy)-8-oxo-7H-purin-9(8H)-yl)methyl)benzamido)ethyl 2,3-bis(oleoyloxy)propyl phosphate

Conditions
ConditionsYield
With 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃;58%
2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic acid

2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic acid

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

(2R)-3-((hydroxy(2-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamido)ethoxy)phosphoryl)oxy)propane-1,2-diyl dioleate

(2R)-3-((hydroxy(2-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamido)ethoxy)phosphoryl)oxy)propane-1,2-diyl dioleate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In chloroform; N,N-dimethyl-formamide at 0 - 20℃; for 6h; Inert atmosphere;55%
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

DOPE-Anisamide

DOPE-Anisamide

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere; Darkness;51%
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

PEG7 Bis-PFP ster

PEG7 Bis-PFP ster

DOPE-PEG7-PFP

DOPE-PEG7-PFP

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃;50%
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

C19H16N2O6

C19H16N2O6

3-(((2-(2-(3-benzoyl-6,7-dimethoxy-2-oxoquinoxalin-1(2H)-yl)acetamido)ethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl dioleate

3-(((2-(2-(3-benzoyl-6,7-dimethoxy-2-oxoquinoxalin-1(2H)-yl)acetamido)ethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl dioleate

Conditions
ConditionsYield
Stage #1: C19H16N2O6 With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide for 0.25h;
Stage #2: 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine In dichloromethane; N,N-dimethyl-formamide at 20℃;
39%
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

PEG-17 bis-NHS-ester

PEG-17 bis-NHS-ester

DOPE-PEG17-NHS

DOPE-PEG17-NHS

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;36%
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

(Z)-(2R)-3-(((2-((2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamido)ethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl dioleate
1415981-98-4

(Z)-(2R)-3-(((2-((2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamido)ethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl dioleate

Conditions
ConditionsYield
Stage #1: all-trans-retinoic-acid With diethylamino-sulfur trifluoride In diethyl ether at -78 - 20℃;
Stage #2: 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine With sodium carbonate In chloroform at 20℃; for 24h;
28%
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

C15H21F2NO4

C15H21F2NO4

C56H97F2N2O11P

C56H97F2N2O11P

Conditions
ConditionsYield
Stage #1: C15H21F2NO4 With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide for 0.5h; Inert atmosphere; Cooling with ice;
Stage #2: 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere; Cooling with ice;
20.8%
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

1,2-distearoyl-sn-glycero-3-phosphoethanolamine
1069-79-0

1,2-distearoyl-sn-glycero-3-phosphoethanolamine

Conditions
ConditionsYield
With acetic acid; platinum Hydrogenation;
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

estra-1,3,5(10)-triene-3,17β-diol 17β-hemisuccinate
7698-93-3, 65684-87-9, 93939-81-2

estra-1,3,5(10)-triene-3,17β-diol 17β-hemisuccinate

(Z)-Octadec-9-enoic acid (R)-2-(hydroxy-{2-[3-((13S,17S)-3-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yloxycarbonyl)-propionylamino]-ethoxy}-phosphoryloxy)-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester
139116-09-9

(Z)-Octadec-9-enoic acid (R)-2-(hydroxy-{2-[3-((13S,17S)-3-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yloxycarbonyl)-propionylamino]-ethoxy}-phosphoryloxy)-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane; acetone for 5h;
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
4004-05-1

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

androst-4-en-3-one-17β-carboxylic acid
302-97-6

androst-4-en-3-one-17β-carboxylic acid

C61H104NO10P
139116-00-0

C61H104NO10P

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 6h; Ambient temperature;

4004-05-1Relevant articles and documents

TREATMENT OF CYSTIC FIBROSIS BY DELIVERY OF NEBULIZED mRNA ENCODING CFTR

-

, (2020/06/08)

The present invention provides, among other things, an improved method of treating cystic fibrosis (CF) in a human subject. The method comprises administering a composition comprising an mRNA encoding a Cystic Fibrosis Transmembrane Conductance Regulator (CFTR) protein at a concentration of 0.5 mg/mL or greater to a human subject via nebulization. The composition is aerosolized using a nebulizer and a nominal dose of the mRNA is administered to the human subject via the nebulizer over a period of time, typically at least 30 minutes, at a suitable nebulization rate, e.g., at least 0.2 mL/minute.

Synthesis of New Phospholipids Linked to Steroid-Hormone Derivatives Designed for Two-Dimensional Crystallization of Proteins

Lebeau, Luc,Oudet, Pierre,Mioskowski, Charles

, p. 1697 - 1706 (2007/10/02)

The synthesis of phospholipids 1n-3n, rationally designed for two-dimensional crystallization of progesterone and estradiol receptors, is reported.The structure of theses lipids provides them with essential properties such as fluidity and stability when spread into monolayers at the air/H2O interface, affinity for the protein to be crystallized, and accessibility of the ligand under the lipid monolayer.

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