75920-10-4

Usage

Uses

Used in Chemical Industry:
1,4,8,11-Tetraazatricyclo[9.3.1.1(4,8)]hexadecane is used as a ligand for metal ion coordination, enabling the formation of stable complexes with various metal ions. This property makes it useful in the development of catalysts and other chemical processes.
Used in Pharmaceutical Industry:
1,4,8,11-Tetraazatricyclo[9.3.1.1(4,8)]hexadecane is used as a catalyst for organic reactions, facilitating the synthesis of various pharmaceutical compounds. Its unique structure allows it to act as an efficient catalyst, improving the yield and selectivity of the reactions.
Used in Materials Science:
1,4,8,11-Tetraazatricyclo[9.3.1.1(4,8)]hexadecane is used as a building block for the synthesis of novel molecular architectures. Its cage-like structure can be incorporated into the design of new materials with unique properties, such as molecular containers, sensors, and drug delivery systems.

InChI:InChI=1/C12H24N4/c1-3-13-7-9-15-5-2-6-16(12-15)10-8-14(4-1)11-13/h1-12H2

Upstream product

• 295-37-4 1,4,8,11-Tetraazacyclotetradecane 
• 50-00-0 formaldehyd 
• 75-09-2 dichloromethane 
• 199275-80-4 1,4,8,11-tetraazabicyclo[9.3.1]pentadecane 
• 294-90-6 1,4,7,10-tetraazacyclododecan 

Downstream Products

• 214078-92-9 1,8-Dimethyl-1,4,8,11-tetraazacyclotetradecane 
• 121187-41-5 1,4-dimethyl-1,4,8,11-tetraazacyclotetradecane 
• 41203-22-9 1,4,8,11-tetramethyl-1,4,8,11-tetra-azacyclotetradecane 
• 214078-93-0 1,8-Dibenzyl-1,4,8,11-tetraazacyclotetradecane 
• 1227479-17-5 1,8-(4-tert-butylbenzyl)-1,4,8,11-tetraazacyclotetradecane 
• 1227479-18-6 1,8-bis(4-(trifluoromethyl)benzyl)-1,4,8,11-tetraazacyclotetradecane 
• 1186198-19-5 H₂(3,5-di(tert-butyl)benzyl)cyclam 
• 1186198-18-4 H₂(3,5-dimethylbenzyl)cyclam 

Relevant academic research and scientific papers

Kinetics Are Crucial When Targeting Copper Ions to Fight Alzheimer's Disease: An Illustration with Azamacrocyclic Ligands

Targeting copper ions to either remove or redistribute them is currently viewed as a possible therapeutic strategy in the context of Alzheimer's disease (AD). Thermodynamic parameters, as for instance the copper(II) affinity of the drug candidate or the copper(II) over zinc(II) selectivity, are considered in the design of the drug candidate. In contrast, kinetic factors have been overlooked despite their probable high importance. In the present article, we use a series of azamacrocyclic ligands to demonstrate that kinetic issues must be taken into account when designing copper-targeting drug candidates in the context of AD.

Non-cross-bridged tetraazamacrocyclic chelator for stable 64Cu-based radiopharmaceuticals

N-mono/dimethylated TE2A tetraazamacrocycles (MM-TE2A and DM-TE2A) were synthesized in high yields. Both Cu-MM/DM-TE2A complexes showed increased kinetic stability compared to that of Cu-TE2A, whereas Cu-DM-TE2A showed even higher in vitro stability than that of Cu-ECB-TE2A. MM-TE2A and DM-TE2A were quantitatively radiolabeled with 64Cu ions and showed rapid clearance from the body to emerge as a potential efficient bifunctional chelator.

Revival of TE2A; A better chelate for Cu(II) ions than TETA?

A highly effective synthetic route for TE2A was developed and the 64Cu-labeled TE2A complexes showed higher kinetic inertness and faster clearance than most commonly used TETA analogs.

Synthesis and Evaluation of 1,8-Disubstituted-Cyclam/Naphthalimide Conjugates as Probes for Metal Ions

Fluorescent molecular probes for metal ions have a raft of potential applications in chemistry and biomedicine. We report the synthesis and photophysical characterisation of 1,8-disubstituted-cyclam/naphthalimide conjugates and their zinc complexes. An ef

New heterobimetallic Cu(II)/Mn(II) complexes with trans-1,8-cyclam derivatives: Synthesis, characterization, magnetic properties and crystal structures of (μ2-Chloro)-(dpc)-copper(II)-trichloro-manganese(II) and two polymorphs of (μ2-Chloro)-(dac)-copper(II)-trichloro-manganese(II)

Two derivatives of cyclam (cyclam = 1,4,8,11-tetraazacyclotetradecane) with propyl- or allyl- (prop-2-en-1-yl) substituents on nitrogen atoms in trans positions, namely 1,8-dipropyl-1,4,8,11-tetraazacyclotetradecane (dpc) and 1,8-diallyl-1,4,8,11-tetraazacyclotetradecane (dac) were prepared and characterized by IR, 1H NMR and 13C NMR spectroscopy. Reaction of dpc and dac with copper(II) chloride gives compounds [Cu(dpc)(H2O)2]Cl2 (1) and [Cu(dac)(H2O)2]Cl2 (3) with similar crystal structures. Compounds 1 and 3 were used as precursors in the synthesis of Cu(II)/Mn(II) complexes 2, 4a and 4b. Prepared complexes were characterized by IR spectroscopy, elemental analysis and their crystal structures were determined using single crystal X-ray analysis. Compounds 4a and 4b are polymorphs, both crystallize in the monoclinic crystal system and the main difference in their crystal structures is in steric arrangement of metal centres within a chain. Moreover, measurements of magnetic susceptibility and Broken Symmetry DFT calculations (BS DFT calculations) carried out for bimetallic complexes 2 and 4a showed that a ferromagnetic exchange interaction J/kB = 2.28 K and J/kB = 2.34 K, respectively, exists within the dinuclear units.

Copper(ii) complexes ofN-propargyl cyclam ligands reveal a range of coordination modes and colours, and unexpected reactivity

The coordination chemistry ofN-functionalised cyclam ligands has a rich history, yet cyclam derivatives with pendant alkynes are largely unexplored. This is despite the significant potential and burgeoning application ofN-propargyl cyclams and related com

Towards the development of a targeted albumin-binding radioligand: Synthesis, radiolabelling and preliminary in vivo studies

Introduction: The compound named 4-[10-(4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanamido)decyl]-11-[10-(β,D-glucopyranos-1-yl)-1-oxodecyl]-1,4,8,11-tetraazacyclotetradecane-1,8-diacetic acid is a newly synthesised molecule capable of binding in vivo to

CoII Complexes as Liposomal CEST Agents

Three paramagnetic CoII macrocyclic complexes containing 2-hydroxypropyl pendant groups, 1,1′,1′′,1′′′-(1,4,8,11-tetraazacyclotetradecane-1,4,8,11-tetrayl)tetrakis- (propan-2-ol) ([Co(L1)]2+, 1,1′-(4,11-dibenzyl-1,4,8,11-tetraazacyclotetradecane-1,8-diyl)bis(propan-2-ol) ([Co(L2)]2+), and 1,1′-(4,11-dibenzyl-1,4,8,11-tetraazacyclotetradecane-1,8-diyl)bis(octadecan-2-ol) ([Co(L3)]2+) were synthesized to prepare transition metal liposomal chemical exchange saturation transfer (lipoCEST) agents. In solution, ([Co(L1)]2+) forms two isomers as shown by 1H NMR spectroscopy. X-ray crystallographic studies show one isomer with 1,8-pendants in cis-configuration and a second isomer with 1,4-pendants in trans-configuration. The [Co(L2)]2+ complex has 1,8-pendants in a cis-configuration. Remarkably, the paramagnetic-induced shift of water 1H NMR resonances in the presence of the [Co(L1)]2+ complex is as large as that observed for one of the most effective LnIII water proton shift agents. Incorporation of [Co(L1)]2+ into the liposome aqueous core, followed by dialysis against a solution of 300 mOsm L?1 produces a CEST peak at 3.5 ppm. Incorporation of the amphiphilic [Co(L3)]2+ complex into the liposome bilayer produces a more highly shifted CEST peak at ?13 ppm. Taken together, these data demonstrate the feasibility of preparing CoII lipoCEST agents.

Tetraazamacrocyclic derivatives and their metal complexes as antileishmanial leads

A total of 44 bis-aryl-monocyclic polyamines, monoaryl-monocyclic polyamines and their transition metal complexes were prepared, chemically characterized, and screened in vitro against the Leishmania donovani promastigotes, axenic amastigotes and intracellular amastigotes in THP1 cells. The IC50 and/or IC90 values showed that 10 compounds were similarly active at about 2-fold less potent than known drug pentamidine against promastigotes. The most potent compound had an IC50 of 2.82 μM (compared to 2.93 μM for pentamidine). Nine compounds were 1.1–13.6-fold more potent than pentamidine against axenic amastigotes, the most potent one being about 2-fold less potent than amphotericin B. Fourteen compounds were about 2–10 fold more potent than pentamidine, the most potent one is about 2-fold less potent than amphotericin B against intracellular amastigotes in THP1 cells. The 2 most promising compounds (FeL7Cl2 and MnL7Cl2), with strong activity against both promastigotes and amastigotes and no observable toxicity against the THP1 cells are the Fe2+- and Mn2+-complexes of a dibenzyl cyclen derivative. Only 2 of the 44 compounds showed observable cytotoxicity against THP1 cells. Tetraazamacrocyclic monocyclic polyamines represent a new class of antileishmanial lead structures that warrant follow up studies.

Copper(ii) complexes for cysteine detection using 19F magnetic resonance

Cysteine plays an essential role in maintaining cellular redox homeostasis and perturbations in cysteine concentration are associated with cardiovascular disease, liver disease, and cancer. 19F MRI is a promising modality for detecting cysteine in biology due to its high tissue penetration and negligible biological background signal. Herein we report fluorinated macrocyclic copper complexes that display a 19F NMR/MRI turn-on response following reduction of the Cu(ii) complexes by cysteine. The reactivity with cysteine was studied by monitoring the appearance of a robust diamagnetic 19F signal following addition of cysteine in conjunction with UV-vis and EPR spectroscopies. Importantly, complexes with-CH2CF3 tags display good water solubility. Studies with this complex in HeLa cells demonstrate the applicability of these probes to detect cysteine in complex biological environments.