109792-60-1

Usage

Uses

Used in Pharmaceutical Industry:
1-Boc-1,12-diaminododecane is used as a chemical intermediate for the synthesis of inhibitors of topoisomerase I, which are employed as anticancer agents. This application is crucial in the development of novel treatments for cancer, as topoisomerase I inhibitors can effectively target and inhibit the enzyme responsible for DNA replication, thereby hindering cancer cell growth.
Used in Chemical Synthesis:
1-Boc-1,12-diaminododecane is used as a PROTAC linker in the synthesis of proteolysis-targeting chimeras (PROTACs). PROTACs are a new class of therapeutics that can selectively degrade target proteins, offering a promising approach to treating various diseases, including cancer and neurodegenerative disorders. The alkane chain with terminal amine and Boc-protected amino groups in 1-Boc-1,12-diaminododecane allows for the efficient conjugation of small molecules to form PROTACs, enhancing their potential as therapeutic agents.

InChI:InChI=1/C17H36N2O2/c1-17(2,3)21-16(20)19-15-13-11-9-7-5-4-6-8-10-12-14-18/h4-15,18H2,1-3H3,(H,19,20)

Upstream product

• 2783-17-7 1,12-Diaminododecane 
• 24424-99-5 di-tert-butyl dicarbonate 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 1538-75-6 2,2-dimethylpropanoic anhydride 

Downstream Products

• 556065-59-9 4-[(1E)-3-({12-[(tert-butoxycarbonyl)amino]dodecyl}amino)-3-oxoprop-1-enyl]phenyl acetate 
• 678188-76-6 tert-butyl [12-(1-phenethylpiperidin-4-ylamino)dodecyl]carbamate 
• 869276-82-4 {12-[3-(2-{4-[2,9-bis-(2,6-diisopropyl-phenyl)-1,3,8,10-tetraoxo-1,2,3,8,9,10-hexahydro-anthra[2,1,9-def;6,5,10-d'e'f']diisoquinolin-5-yloxy]-phenyl}-ethylcarbamoyl)-acryloylamino]-dodecyl}-carbamic acid tert-butyl ester 
• 869276-87-9 {12-[3-(2-{4-[2,9-bis-(2,6-diisopropyl-phenyl)-1,3,8,10-tetraoxo-1,2,3,8,9,10-hexahydro-anthra[2,1,9-def;6,5,10-d'e'f']diisoquinolin-5-yloxy]-phenyl}-ethylcarbamoyl)-acryloylamino]-dodecyl}-carbamic acid tert-butyl ester 
• 678188-90-4 N-[12-(N²,N³-bis(tert-butoxycarbonyl)guanidino)dodecyl]-N-(1-phenethylpiperidin-4-yl)propanamide 
• 678188-81-3 tert-butyl {12-[(1-phenethylpiperidin-4-yl)propionylamino]dodecyl}carbamate 
• 678188-86-8 N-(12-amino-dodecyl)-N-(1-phenethyl-piperidin-4-yl)-propionamide 
• 678188-90-4 C₃₉H₆₇N₅O₅ 
• 1169975-36-3 N-(12-(tert-butyl-carbamoyloxy)dodecyl)-3,4,5-trisbenzyloxybenzamide 

Relevant academic research and scientific papers

A new perylene bisimide bola amphiphile: Synthesis, characterization, fluorescent properties and applications as a potential probe

Fluorescently-tagged lipids are a powerful tool for investigating the dynamics of lipids in cell biological studies and in biophysical applications. Herein we report the synthesis and the characterization of a new bola amphiphile, PC12, based on a bisimidic perylene moiety: a central perylene unit is symmetrically linked to two aliphatic chains both ending with a quaternary ammonium group. Absorption and fluorescent properties of the newly synthesized compound were investigated in DMSO and in water as a function of concentration and temperature. Further, the entrapment efficiency, the fluorescence behavior in dimyristoyl-sn-glycero-phosphocholine (DMPC) liposomes, and cell uptake on human and murine glioblastoma cell lines were evaluated. When loaded in liposomes, PC12 follows the same destiny of liposomes themselves in the cell cultures: this is an interesting result because PC12 could be used both as an aspecific dye (free form) and as an organelle-specific lipid probe.

Identification of nuclear proteins that interact with platinum-modified DNA by photoaffinity labeling

Interactions between cellular proteins and cisplatin-modified DNA are important in determining the anticancer activity of the drug. To develop a general approach for identifying proteins that mediate cellular responses to cisplatin, photoreactive cisplati

Solvent-dependent self-assembly and morphological transition of low-molecular-weight azobenzene organogel

A novel low molecular weight organogelator (LMOG) containing an azobenzene group has been designed and synthesized. Stable gels could be formed in various organic solvents. UV–Vis spectroscopy indicated that the sol-gel transition of the organogels could be reversibly tuned by UV/visible light irradiations. Importantly, scanning electron microscopy (SEM) revealed that the characteristic gelation morphologies would vary from solvents of different polarities. FT-IR, XRD and rheological measurements demonstrated that the different nanostructures in polar and non-polar solvents might result from the differences in the intermolecular hydrogen bonding, π-π stacking driving forces as well as the different stacking models for the formation of the gels. Moreover, as an efficient phase-selective gelator, this photo-switchable gel could perform as an efficient absorbent and water cleaner to remove pollutants (e.g. rhodamine B).

Synthesis of dimeric acridine derived nucleic acid intercalators

A series of antiviral compounds consisting of an intercalating acridine derived part, a spacer region and a reactive EDTA-derived conjugate was synthesized in an easy sequence. Suitably monoprotected 1,ω-alkyldiamines gave upon reaction with 6,9-dichloro-2-methoxyacridine (1) followed by deprotection and reaction with EDTA dianhydride the target molecules. In the presence of ascorbate a reduction of the phage-titer of the MS2 phages by > 8 logarithmic decades was achieved.

Investigation of the lactam side chain length necessary for optimal indenoisoquinoline topoisomerase I inhibition and cytotoxicity in human cancer cell cultures

Indenoisoquinolines with lactam substituents such as ethylamino, propylamino, and butylamino have previously demonstrated potent biological activity, but an optimal length has never been established. In the present study, a series of simplified indenoisoquinoline analogues possessing a linker spacing of 0-12 carbon atoms between the lactam nitrogen and the terminal amino group have been prepared, determining that 2-4-atom lengths are optimal for topoisomerase I inhibition and cytotoxicity. Using these lengths, analogues were prepared with the amino group and portions of the linker replaced by a pyridine ring. A three-carbon spacer within the pyridine series still demonstrated potent topoisomerase I inhibition.

Structure-Activity Relationship of Hetarylpropylguanidines Aiming at the Development of Selective Histamine Receptor Ligands?

New classes of alkylated hetarylpropylguanidines with different functionality and variation in spacer length were synthesized to determine their behavior at the four histamine receptor (H1R, H2R, H3R, H4R) subtypes. Alkylated guanidines with different terminal functional groups and varied basicity, like amine, guanidine and urea were developed, based on the lead structure SK&F 91486 (2). Furthermore, heteroatomic exchange at the guanidine structure of 2 led to simple analogues of the lead compound. Radioassays at all histamine receptor subtypes were accomplished, as well as organ bath studies at the guinea pig (gp) ileum (gpH1R) and right atrium (gpH2R). Ligands with terminal functionalization led to, partially, highly affine and potent structures (two digit nanomolar), which showed up a bad selectivity profile within the histamine receptor family. While the benzoylurea derivative 144 demonstrated a preference towards the human (h) H3R, S-methylisothiourea analogue 143 obtained high affinity at the hH4R (pKi=8.14) with moderate selectivity. The molecular basis of the latter finding was supported by computational studies.

Compositions comprising a biocidal polyamine

Compounds, compositions, and methods comprising a polyamine compound are described, which may be used to kill, disperse, treat, reduce biofilms, and/or inhibit or substantially prevent biofilm formation. In certain aspects, the present invention relates t

Efficient phosphodiester cleaving nanozymes resulting from multivalency and local medium polarity control

The self-organization of Zn(II) complexes on the surface of 1.6-nm diameter gold nanoparticles (nanozymes) allows the spontaneous formation of multiple bimetallic catalytic sites capable to promote the cleavage of a RNA model substrate. We show that by tu

LDV peptidomimetics equipped with biotinylated spacer-arms: Synthesis and biological evaluation on CCRF-CEM cell line

The tripeptide Leu-Asp-Val (LDV) is known to bind α4β 1 integrin in leukemia cells. Here we have synthesized a LDV peptidomimetic equipped with a biotin-conjugated spacer-arm. Compound 9 acts as an inhibitor of the α4β1 integrin in an adhesion assay using fluorescently labeled, α4β 1 integrin-expressing leukemia CCRF-CEM cells. Furthermore, when bound to neutravidin-coated plates, compound 9 could capture CCRF-CEM cells. Such biotin-conjugated LDV peptidomimetic may thus represent a novel tool for biotechnological applications using avidin interaction for leukapheresis or leukemia cell targeting.

Synthesis and biological evaluation of the first dual tyrosyl-DNA phosphodiesterase i (Tdp1)-topoisomerase i (Top1) inhibitors

Substances with dual tyrosyl-DNA phosphodiesterase I-topoisomerase I inhibitory activity in one low molecular weight compound would constitute a unique class of anticancer agents that could potentially have significant advantages over drugs that work against the individual enzymes. The present study demonstrates the successful synthesis and evaluation of the first dual Top1-Tdp1 inhibitors, which are based on the indenoisoquinoline chemotype. One bis(indenoisoquinoline) had significant activity against human Tdp1 (IC 50 = 1.52 ± 0.05 μM), and it was also equipotent to camptothecin as a Top1 inhibitor. Significant insights into enzyme-drug interactions were gained via structure-activity relationship studies of the series. The present results also document the failure of the previously reported sulfonyl ester pharmacophore to confer Tdp1 inhibition in this indenoisoquinoline class of inhibitors even though it was demonstrated to work well for the steroid NSC 88915 (7). The current study will facilitate future efforts to optimize dual Top1-Tdp1 inhibitors.