4246-51-9

Basic information

• Product Name: 4,7,10-TRIOXA-1,13-TRIDECANEDIAMINE
• Synonyms: BIS[2-(3-AMINOPROPOXY)ETHYL] ETHER;DIETHYLENE GLYCOL BIS(3-AMINOPROPYL) ETHER;DCA 221;ALPHA, OMEGA,-BIS-(3-AMINOPROPYL)-DIETHYLENEGLYCOL ETHER;4,7,10-TRIOXA-1,13-TRIDECANEDIAMINE;1,13-DIAMINO-4,7,10-TRIOXATRIDECANE;3,3'-OXYBIS(ETHYLENE-OXY)BIS(PROPYLAMINE);O,O'-BIS(3-AMINOPROPYL)DIETHYLENE GLYCOL
• CAS NO: 4246-51-9
• Molecular Formula: C₁₀H₂₄N₂O₃
• Molecular Weight: 220.31
• EINECS: 224-207-2
• Mol File: 4246-51-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: -32 °C
• Boiling Point: 146-148 °C4 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.005 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000594mmHg at 25°C
• Refractive Index: n20/D 1.464(lit.)
• Storage Temp.: Store below +30°C.
• PKA: 10.00±0.10(Predicted)
• Explosive Limit: 1.1-4.5%(V)
• BRN: 1760709
• CAS DataBase Reference: 4,7,10-TRIOXA-1,13-TRIDECANEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,7,10-TRIOXA-1,13-TRIDECANEDIAMINE(4246-51-9)
• EPA Substance Registry System: 4,7,10-TRIOXA-1,13-TRIDECANEDIAMINE(4246-51-9)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2735 8/PG 3
• WGK Germany: 2
• RTECS: ID6475000
• F: 10-34
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 4246-51-9(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light yellow liquid

General Description

4,7,10-Trioxa-1,13-tridecanediamine can be used as a surface passivation agent for the synthesis of photoluminescent carbon nanodots for semiconductor applications.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C10H24N2O3/c11-3-1-5-13-7-9-15-10-8-14-6-2-4-12/h1-12H2/p+2

Synthetic route

bis(2-(2-cyanoethoxy)ethyl)ether (22397-31-5) → 4,7,10-trioxa-1,13-diaminotridecane (4246-51-9)

Conditions	Yield
With ammonia; nickel at 110℃; under 58840.6 Torr; Hydrogenation;
With hydrogen; nickel In propan-1-ol

3-(2-(2-hydroxyethoxy)ethoxy)propanenitrile (10143-54-1) + bis(2-(2-cyanoethoxy)ethyl)ether (22397-31-5) → 4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + 2-[2-(3-amino-propoxy)-ethoxy]-ethanol (112-33-4) + diethylene glycol (111-46-6)

Conditions	Yield
With hydrogen; Grace 2724 sponge cobalt In water at 60℃; under 42133 Torr; for 4h; Product distribution / selectivity;

3-(2-(2-hydroxyethoxy)ethoxy)propanenitrile (10143-54-1) + bis(2-(2-cyanoethoxy)ethyl)ether (22397-31-5) → aminopropyldiaminopropyldiethyleneglycol + C16H38N4O3 + 4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + 2-[2-(3-amino-propoxy)-ethoxy]-ethanol (112-33-4)

Conditions	Yield
With hydrogen; Grace 2724 sponge cobalt In methanol at 120℃; under 42133 Torr; for 5h; Product distribution / selectivity;
With hydrogen; Grace 2724 sponge cobalt In DMF (N,N-dimethyl-formamide) at 120℃; under 42133 Torr; for 5h; Product distribution / selectivity;
With hydrogen; Grace 2724 sponge cobalt In tert-butyl methyl ether at 120℃; under 42133 Torr; for 5h; Product distribution / selectivity;

3-(2-(2-hydroxyethoxy)ethoxy)propanenitrile (10143-54-1) + bis(2-(2-cyanoethoxy)ethyl)ether (22397-31-5) → aminopropyldiaminopropyldiethyleneglycol + 4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + 2-[2-(3-amino-propoxy)-ethoxy]-ethanol (112-33-4)

Conditions	Yield
With hydrogen; Grace 2724 sponge cobalt at 125℃; under 47304.6 Torr; for 4h; Product distribution / selectivity;
With hydrogen; Grace 2724 sponge cobalt In tetrahydrofuran at 120℃; under 42133 Torr; for 5h; Product distribution / selectivity;

3-(2-(2-hydroxyethoxy)ethoxy)propanenitrile (10143-54-1) + bis(2-(2-cyanoethoxy)ethyl)ether (22397-31-5) → 4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + 2-[2-(3-amino-propoxy)-ethoxy]-ethanol (112-33-4)

Conditions	Yield
With hydrogen; Grace 2724 sponge cobalt In tert-butyl methyl ether at 120℃; under 42133 Torr; for 5h; Product distribution / selectivity;
With hydrogen; Grace 2724 sponge cobalt In tetrahydrofuran at 120℃; under 42133 Torr; for 5h; Product distribution / selectivity;

2-[2-[2-[2-aminoethoxy]ethoxy]ethoxy]ethylamine (929-75-9) + 1(4)-methoxy-7,10,13-trioxa-3,17-diaza-1(2,6)-pyridinaoctadecacyclophan-2,17-diene (1073123-93-9) → 4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + 1(4)-methoxy-6,9,12-trioxa-3,15-diaza-1(2,6)-pyridinahexadecacyclophan-2,15-diene (1073123-92-8)

Conditions	Yield
In d(4)-methanol at 20℃; for 12h;

carbon disulfide (75-15-0) + 4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) → 1-isothiocyanato-3-(2-(2-(3-isothiocyanatopropoxy)ethoxy)ethoxy)propane

Conditions	Yield
Stage #1: carbon disulfide; 4,7,10-trioxa-1,13-diaminotridecane With triethylamine In ethanol at 20℃; Stage #2: With dmap; di-tert-butyl dicarbonate In ethanol at 20℃; for 0.25h; Further stages.;	100%
Stage #1: carbon disulfide; 4,7,10-trioxa-1,13-diaminotridecane With triethylamine In N,N-dimethyl-formamide at 0℃; Stage #2: With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide at 0℃; for 0.25h;

glutaric anhydride, (108-55-4) + 4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) → C20H36N2O9 (1411773-83-5)

Conditions	Yield
With triethylamine In tetrahydrofuran for 0.5h;	100%

4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + C23H28N2O3 → C30H48N2O6

Conditions	Yield
In N,N-dimethyl-formamide; acetonitrile at 20℃; for 12h; Inert atmosphere;	100%

4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl N-(3-{2-[2-(3-aminopropoxy)ethoxy]ethoxy}propyl)carbamate (194920-62-2)

Conditions	Yield
In 1,4-dioxane Inert atmosphere;	99%
In 1,4-dioxane	98%
In 1,4-dioxane; water at 20℃; for 17h;	96%

4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + p-nitrophenoxycarbonyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside (1233921-11-3) → N,N'-bis-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyloxycarbonyl)-4,7,10-trioxa-1,13-tridecandiamine (1233921-16-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 2h;	99%
With N-ethyl-N,N-diisopropylamine In dichloromethane

4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + biotin pentafluorophenyl ester (120550-35-8) → N-(13-amino-4,7,10-trioxatridecanyl)-D-biotinamide (183896-00-6)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Inert atmosphere;	99%
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 1.25h;	94%
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 1.5h;	71%

4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + 1H,2H,2H-perfluoro-1-octyl succinic acid monoester (125111-32-2) → 2C12H9F13O4*C10H24N2O3

Conditions	Yield
In methanol Heating;	99%

4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + 1H,1H,2H,2H-perfluoro-1-decyl succinic acid monoester → 2C14H9F17O4*C10H24N2O3

Conditions	Yield
In methanol Heating;	99%

4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + 3,3,4,4,5,5,6,6,7,7,8,8,8,9,10,10,10,10-heptadecafluoro-1-decathioacetic acid (54207-61-3) → C12H7F17O2S*C10H24N2O3

Conditions	Yield
In methanol for 2h; Reflux;	99%

4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-octanethioacetic acid (123708-11-2) → C10H7F13O2S*C10H24N2O3

Conditions	Yield
In methanol for 2h; Reflux;	99%

4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-octa-6-thiohexanoic acid (220072-62-8) → C14H15F13O2S*C10H24N2O3

Conditions	Yield
In methanol for 2h; Reflux;	99%

4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) → O,O'-bis(3-azidopropyl)diethylene glycol

Conditions	Yield
With imidazole-1-sulfonyl azide hydrochloride; potassium carbonate; copper(II) sulfate In methanol; water at 20℃; for 2h;	98%
With triflic azide; sodium hydrogencarbonate; copper(II) sulfate In methanol; dichloromethane; water at 20℃; for 2h;	95%
With triflic azide; sodium hydrogencarbonate; copper(II) sulfate In methanol; dichloromethane; water at 20℃; for 0.5h;

methyl 3-(N,N-diethylamino)propionate (5351-01-9) + 4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) → C24H50N4O5

Conditions	Yield
With sodium methylate In methanol at 40℃; for 7h;	98%

o-fluorobromobenzene (1072-85-1) + 4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) → N,N'-(((oxybis(ethan-2,1-diyl))bis(oxy))bis(propane-3,1-diyl))bis(2-fluoroaniline)

Conditions	Yield
Stage #1: o-fluorobromobenzene With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane Inert atmosphere; Stage #2: 4,7,10-trioxa-1,13-diaminotridecane With sodium t-butanolate In 1,4-dioxane for 8h; Reagent/catalyst; Reflux;	98%

4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + 3,3,4,4,5,5,6,6,7,7,8,8,9,9,9,10,10,10-heptadecafluoro-1-decane-6-thiohexanoic acid → C16H15F17O2S*C10H24N2O3

Conditions	Yield
In methanol for 2h; Reflux;	98%

4,6-dichloropyrimidine (1193-21-1) + 4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) → N,N'-bis(6-chloropyrimidin-4-yl)-4,7,10-trioxatridecane-1,13-diamine (1253643-94-5)

Conditions	Yield
With caesium carbonate In 1,4-dioxane at 100℃; for 7h; Inert atmosphere;	97%

4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + Fmoc-Tyr(tBu)-OH (71989-38-3) → C66H78N4O11 (1402012-45-6)

Conditions	Yield
Stage #1: Fmoc-Tyr(tBu)-OH With benzotriazol-1-ol In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 4,7,10-trioxa-1,13-diaminotridecane In N,N-dimethyl-formamide at 20℃; for 0.5h;	97%

4-chloro-3,5-dinitrobenzotrifluoride (393-75-9) + 4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) → N,N'-Bis(2',6'-dinitro-4'-trifluoromethylphenyl)-4,7,10-trioxa-1,13-tridecadiamine (129199-90-2)

Conditions	Yield
With triethylamine In ethanol at 70℃; for 5.5h;	96.4%

4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + acrylonitrile (107-13-1) → 3-[{3-[2-(2-{3-[bis-(2-cyano-ethyl)-amino]-propoxy}-ethoxy)-ethoxy]-propyl}-(2-cyano-ethyl)-amino]-propionitrile

Conditions	Yield
In water at 5 - 80℃; for 25h; Michael reaction;	96%

4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + trifluoromethylsulfonic anhydride (358-23-6) → N-(3-{2-[2-(3-aminopropoxy)ethoxy]ethoxy}propyl)-trifluoromethanesulfonamide (1110783-61-3)

Conditions	Yield
In chloroform at 0 - 20℃; for 16.5h;	96%

4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → 9H-fluoren-9-ylmethyl N-(3-{2-[2-(3-aminopropoxy)ethoxy]ethoxy}propyl)carbamate (308241-31-8)

Conditions	Yield
In tetrahydrofuran; isopropyl alcohol at -10℃;	95%
Stage #1: 4,7,10-trioxa-1,13-diaminotridecane With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine In dichloromethane at 5 - 20℃; for 3h; Stage #2: (fluorenylmethoxy)carbonyl chloride In dichloromethane at 3 - 20℃; for 5h;

[4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl]acetic acid (202592-28-7) + 4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) → N-(3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propyl)-2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetamide

Conditions	Yield
Stage #1: [4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl]acetic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 4,7,10-trioxa-1,13-diaminotridecane With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h;	95%

4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid (2900-27-8) → C36H54N4O9 (1412423-32-5)

Conditions	Yield
With 2,4,6-trimethyl-pyridine; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide at 0℃; for 2h;	94%

4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + 3-cyanobromobenzene (6952-59-6) → 3,3'-((((oxybis(ethane-2,1-diyl))bis(oxy))bis(propane-3,1-diyl))bis(azanediyl))dibenzonitrile

Conditions	Yield
Stage #1: 3-cyanobromobenzene With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane Inert atmosphere; Stage #2: 4,7,10-trioxa-1,13-diaminotridecane With sodium t-butanolate In 1,4-dioxane for 8h; Reagent/catalyst; Reflux;	94%

4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + 3-cyanobromobenzene (6952-59-6) → ((((Oxybis(ethane-2,1-diyl))bis(oxy))bis(propane-3,1-diyl))(bis(azanediyl))bis(3,1-phenylene))bis(phenylmethanone)

Conditions	Yield
Stage #1: 3-cyanobromobenzene With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane Inert atmosphere; Stage #2: 4,7,10-trioxa-1,13-diaminotridecane With sodium t-butanolate In 1,4-dioxane for 8h; Reflux;	94%

4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + biotin N-Hydroxysuccinimide ester (35013-72-0) → N-(13-amino-4,7,10-trioxatridecanyl)-D-biotinamide (183896-00-6)

Conditions	Yield
In N,N-dimethyl-formamide for 1h; Inert atmosphere;	93%
With triethylamine In N,N-dimethyl-formamide at 20℃; for 72h;	67%
In dimethyl sulfoxide at 20℃; for 0.25h;	15 mg

4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + acrylic acid methyl ester (292638-85-8) → 3-[{3-[2-(2-{3-[bis-(2-methoxycarbonyl-ethyl)-amino]-propoxy}-ethoxy)-ethoxy]-propyl}-(2-methoxycarbonyl-ethyl)-amino]-propionic acid methyl ester

Conditions	Yield
In water at 5 - 80℃; for 25h; Michael reaction;	93%

4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + [(Z)-4-(p-nitrophenoxycarbonyloxy)-but-2-en-1-yl]-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (324532-88-9) → N,N'-bis-(4-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)-(Z)-but-2-enyloxycarbonyl)-4,7,10-trioxa-1,13-tridecanediamine (959923-99-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 3h;	92%

4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + 9-Bromoanthracene (1564-64-3) + (3β,5β)-3,24-bis(6-chloropyridin-2-yloxy)cholane (1185506-80-2) → N,N'-{3,3'-[butane-1,4-diyldi(oxy)]bis(propane-3,1-diyl)}di(anthracen-9-amine) (1224736-91-7) + N-[3-(2-{2-[3-(9-anthrylamino)propoxy]ethoxy}ethoxy)propyl]-6-({(3β,5β)-24-[(6-{[3-(2-{2-[3-(9-anthrylamino)propoxy]ethoxy}ethoxy)propyl]amino}pyridin-2-yl)oxy]cholan-3-yl}oxy)pyridin-2-amine (1224736-89-3)

Conditions

Yield

Stage #1: 4,7,10-trioxa-1,13-diaminotridecane; (3β,5β)-3,24-bis(6-chloropyridin-2-yloxy)cholane With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In 1,4-dioxane for 4h; Reflux; Inert atmosphere; Stage #2: 9-Bromoanthracene With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In 1,4-dioxane for 4h; Reflux; Inert atmosphere;

A 92% B 10%

4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + 4,4'-dimethoxytrityl chloride (40615-36-9) → 3-{2-[2-(3-{[Bis-(4-methoxy-phenyl)-phenyl-methyl]-amino}-propoxy)-ethoxy]-ethoxy}-propylamine

Conditions	Yield
In tetrahydrofuran	91%
With triethylamine In acetonitrile

Upstream product

• 929-75-9 2-[2-[2-[2-aminoethoxy]ethoxy]ethoxy]ethylamine 
• 1073123-93-9 1⁽⁴⁾-methoxy-7,10,13-trioxa-3,17-diaza-1(2,6)-pyridinaoctadecacyclophan-2,17-diene 
• 10143-54-1 3-(2-(2-hydroxyethoxy)ethoxy)propanenitrile 
• 22397-31-5 bis(2-(2-cyanoethoxy)ethyl)ether 

Downstream Products

• 927888-44-6 3-(2-(2-(3-(trityl-amino)-propoxy)-ethoxy)-ethoxy)-propylamine 
• 1419872-67-5 C₅₅H₈₅N₁₃O₁₈S 
• 1246993-51-0 C₃₄H₄₂N₂O₄ 
• 1351636-81-1 C₃₁H₅₀N₄O₁₁ 
• 1351636-85-5 C₂₉H₄₆N₆O₁₃ 
• 1351636-86-6 C₂₈H₄₄N₆O₁₃ 
• 1351636-87-7 C₃₂H₄₇N₇O₁₅ 
• 1351636-88-8 C₄₈H₇₂N₁₂O₁₆S 
• 220156-99-0 benzyl (3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propyl)carbamate 
• 1435052-29-1 C₂₆H₃₆N₂O₇ 
• 1058165-51-7 N-(3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propyl)-2,4-dinitroaniline 
• 183896-00-6 N-(13-amino-4,7,10-trioxatridecanyl)-D-biotinamide 
• 874306-45-3 N-(3-{2-[2-(3-aminopropoxy)ethoxy]ethoxy}propyl)-3-([(3β,5β,17α,20S)-24-{3-[(3-{2-[2-(3-aminopropoxy)ethoxy]ethoxy}propyl)amino]phenoxy}cholan-3-yl]oxy)aniline 

Relevant articles and documents

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