170908-81-3

Basic information

• Product Name: 1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic acid, 1-(2,5-dioxo-1-pyrrolidinyl) ester
• Synonyms: 1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic acid, 1-(2,5-dioxo-1-pyrrolidinyl) ester;DOTA-NHS-ester;DOTA-NHS-ester(B-280);DOTA mono-N-hydroxysuccinimide ester
• CAS NO: 170908-81-3
• Molecular Formula: C₂₀H₃₁N₅O₁₀
• Molecular Weight: 501.48764
• Mol File: 170908-81-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 743.651 °C at 760 mmHg
• Flash Point: 403.546 °C
• Appearance: /
• Density: 1.516 g/cm³
• PKA: 2.46±0.10(Predicted)
• CAS DataBase Reference: 1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic acid, 1-(2,5-dioxo-1-pyrrolidinyl) ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic acid, 1-(2,5-dioxo-1-pyrrolidinyl) ester(170908-81-3)
• EPA Substance Registry System: 1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic acid, 1-(2,5-dioxo-1-pyrrolidinyl) ester(170908-81-3)

Safety Data

• Hazardous Substances Data: 170908-81-3(Hazardous Substances Data)

Usage

Uses

DOTA-NHS-ester is a bifunctional chelator.

Upstream product

• 819869-77-7 tri-tert-butyl 2,2’,2”-(10-(2-((2,5-dioxopyrrolidin-1-yl)oxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate 
• 825625-07-8 tri-tert-butyl 2,2’,2’‘-(10-(2-ethoxy-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate 
• 137076-54-1 1,4,7-tris(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane-10-acetic acid 
• 122555-91-3 1,4,7-tris-tert-butoxycarbonylmethyl-1,4,7,10-tetraazacyclododecane 
• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 60239-18-1 1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane 
• 294-90-6 1,4,7,10-tetraazacyclododecan 
• 192635-89-5 phenylmethyl 2-(1,4,7,10-Tetraaza-4,7,10-tris(((tert-butyl)oxycarbonyl)methyl)cyclododecyl)-acetate 

Downstream Products

• 1009319-55-4 10-(2-(2-(4-((1E,3E)-3-ethoxycarbonyl-5-hydroxypenta-1,3-dienyl)-phenylamino)-2-oxoethylamino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid 
• 1004552-65-1 Gd(C₈H₁₆N₄(CH₂COO)3CH₂CONHCH₂CH₂C₆H₃(OH)2) 
• 909024-55-1 DOTA-cyclo-RGDfK 
• 424838-61-9 C₅₇H₇₄N₁₄O₁₆ 
• 1448229-18-2 C₃₂H₄₅N₇O₁₁S 
• 1588764-91-3 C₆₃H₁₀₂N₂₂O₁₉ 
• 1588764-94-6 C₄₆H₇₀N₁₆O₁₄ 

Relevant articles and documents

Preparation, quality control and biodistribution studies of two [ 111In]-rituximab immunoconjugates

In order to use Auger-electron therapeutic effects in CD20 antigen targeting in lymphomas, Mabthera (rituximab) was successively labeled with [111In]-indium chloride (185 MBq) after conjugation with freshly prepared macrocyclic bifunctional chelating agent, N-succinimidyl-1,4,7,10- tetraazacyclododecane-1,4,7,10-tetra-acetic acid (DOTA-NHS) and ccDTPA separately. Conjugated-Rituximab was obtained by the addition of 1 ml of a rituximab pharmaceutical solution (5 mg/ml, in phosphate buffer, pH=7.8) to a glass tube pre-coated with freshly prepared DOTA-NHS or ccDTPA (0.01-0.1 mg) at 25°C. Radiolabeling was performed at 37°C in 3h and room temperature for one hour for DOTA-conjugate and DTPA-conjugate respectively. HPLC showed an overall radiochemical purity of 97.5 and 95% for DOTA and DTPA-conjugates respectively (Specific activity =2800-5600 GBq/mM). The final isotonic 111In-rituximab complexes were checked by gel electrophoresis for radiolysis. Preliminary biodistribution studies in normal rat model performed to determine radioimmunoconjugates distribution of up to 48h. Oesterreichische Apotheker-Verlagsgesellschaft m. b. H.

Development of 170Tm-DOTA-cetuximab for radioimmunotherapy

Thulium-170 [T1/2=128.4days, Eβ(max)=968keV, Eγ=84keV (3.26%)] has radionuclidic properties suitable for use in therapy. 170Tm can be produced by a relatively feasible route involving thermal neutron bombardment on natural Tm(NO3)3 (100% 169Tm) in medium flux research reactors. The combination of beta-particle emission of Tm-170 with therapeutic properties of C225 monoclonal antibody (cetuximab) as well as optimization studies for future Tm-167 labeling was targeted in this study. Conjugated cetuximab was obtained by the addition of 0.5ml of a cetuximab pharmaceutical solution (1mg, in phosphate buffer, pH7.8) to a glass tube pre-coated with in situ prepared 1,4,7,10-tetraazacyclododecane- N,N,N,N-tetraacetic acid mono-(N-hydroxysuccinimidyl) ester (DOTA-NHS) (～5mg) at 25°C. Cetuximab was labeled with 170Tm-Thulium chloride (100MBq) after conjugation with DOTA-NHS in 2-3h (radiochemical purity >99%, instant thin-layer chromatography, specific activity=77-385TBq/mmol). Biodistribution studies in wild-type rats for free Tm-170 and the radioimmunoconjugate were performed to determine the distribution up to 72h. A comparative time-frame study was performed for critical organs for both radiochemical species. The major organs of accumulation were shown to be the lung, liver, and spleen, respectively.

CONJUGATES OF THE B-SUBUNIT OF SHIGA TOXIN FOR USE AS CONTRASTING AGENTS FOR IMAGING AND THERAPY

Multivalent conjugates comprising the following formula: (STxB-linker A-S)x-GNS-(S-linker B-T)y wherein STxB is the B-subunit of Shiga toxin; linker A is a noncleavable linker; linker B is a cleavable linker used to release at least