177213-61-5

Basic information

• Product Name: N2,N3-BIS-(TERT-BUTYLOXYCARBONYL)-1,5,10,14-TETRA-AZA-QUATRODECANE
• Synonyms: N2,N3-BIS-(TERT-BUTYLOXYCARBONYL)-1,5,10,14-TETRA-AZA-QUATRODECANE;SPERMINE(HBBH);N2,N3-Bis-(t-butyloxycarbonyl)-1,5,10,14-tetra-aza-quatrodecan;N4,N9-di-Boc-spermine≥ 98% (TLC)
• CAS NO: 177213-61-5
• Molecular Formula: C₂₀H₄₂N₄O₄
• Molecular Weight: 402.57
• Mol File: 177213-61-5.mol
• Article Data: 25

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N2,N3-BIS-(TERT-BUTYLOXYCARBONYL)-1,5,10,14-TETRA-AZA-QUATRODECANE(CAS DataBase Reference)
• NIST Chemistry Reference: N2,N3-BIS-(TERT-BUTYLOXYCARBONYL)-1,5,10,14-TETRA-AZA-QUATRODECANE(177213-61-5)
• EPA Substance Registry System: N2,N3-BIS-(TERT-BUTYLOXYCARBONYL)-1,5,10,14-TETRA-AZA-QUATRODECANE(177213-61-5)

Safety Data

• Hazardous Substances Data: 177213-61-5(Hazardous Substances Data)

Usage

Description

N2,N3-BIS-(TERT-BUTYLOXYCARBONYL)-1,5,10,14-TETRA-AZA-QUATRODECANE, also known as N4, N9-di-Boc-spermine, is a spermine linker that contains two Boc-protected amino groups and two amine groups. The Boc groups can be deprotected under mild acidic conditions to form the free amine. The amino groups are reactive with carboxylic acids, activated NHS esters, carbonyls (ketone, aldehyde), etc. Spermine is a polyamine that modulates various cellular activities like cellular development and differentiation, stability of DNA, and apoptosis. It is a colorless oil.

Uses

Used in Chemical Synthesis:
N2,N3-BIS-(TERT-BUTYLOXYCARBONYL)-1,5,10,14-TETRA-AZA-QUATRODECANE is used as a building block for the synthesis of various complex molecules, including pharmaceuticals and bioactive compounds, due to its reactive amino groups and Boc-protected functionality.
Used in Drug Delivery Systems:
In the pharmaceutical industry, N2,N3-BIS-(TERT-BUTYLOXYCARBONYL)-1,5,10,14-TETRA-AZA-QUATRODECANE is used as a component in drug delivery systems to improve the solubility, stability, and bioavailability of therapeutic agents. Its Boc-protected amino groups can be utilized to attach drug molecules or targeting ligands, enhancing the specificity and efficacy of drug delivery.
Used in Bioconjugation:
N2,N3-BIS-(TERT-BUTYLOXYCARBONYL)-1,5,10,14-TETRA-AZA-QUATRODECANE is used as a bioconjugation agent for the attachment of biomolecules, such as proteins, peptides, or nucleic acids, to other molecules or surfaces. The reactive amino groups facilitate the formation of stable covalent bonds with various functional groups present in the target biomolecules.
Used in Materials Science:
In the field of materials science, N2,N3-BIS-(TERT-BUTYLOXYCARBONYL)-1,5,10,14-TETRA-AZA-QUATRODECANE is used as a component in the development of novel materials with specific properties, such as self-assembling systems, sensors, or stimuli-responsive materials. The spermine linker can provide a versatile platform for the integration of different functional groups and molecular recognition elements.

Upstream product

• 193560-26-8 N₁,N₁₂-ditrifluoroacetyl-N₄,N₉-di(t-butoxycarbonyl)-1,12-diamino-4,9-diazadodecane 
• 194808-59-8 N⁴,N⁹-di(tert-butyloxycarbonyl)-3-(4-[(2-cyanoethyl)amino]butylamino)propanenitrile 
• 267410-81-1 [4-(tert-butoxycarbonyl-{3-[1-(4,4-dimethyl-2,6-dioxo-cyclohexylidene)-ethylamino]-propyl}-amino)-butyl]-{3-[1-(4,4-dimethyl-2,6-dioxo-cyclohexylidene)-ethylamino]-propyl}-carbamic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 109-76-2 Trimethylenediamine 
• 227758-39-6 2-(1-((3-hydroxypropyl)amino)ethylidene)-5,5-dimethylcyclohexane-1,3-dione 
• 301206-98-4 2-(1-((4-hydroxybutyl)amino)ethylidene)-5,5-dimethylcyclohexane-1,3-dione 
• 71-44-3 Spermine 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 267410-80-0 C₃₀H₅₀N₄O₄ 
• 14209-32-6 3-(4-[(2-cyanoethyl)amino]butylamino)propanenitrile 
• 168788-09-8 N¹,N¹²-di(trifluoroacetyl)-1,12-diamino-4,9-diazadodecane 

Downstream Products

• 144117-44-2 Philanthotoxin 343 tris(trifluoroacetate) salt 
• 1643592-87-3 C₄₀H₅₄Br₄N₄O₈ 
• 1643593-18-3 C₄₀H₅₂Br₆N₄O₈ 
• 1643593-19-4 C₄₀H₅₂Br₆N₄O₈ 
• 1643592-89-5 C₃₅H₅₅Br₃N₄O₈ 

Relevant articles and documents

Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule

Carbonic anhydrases (CAs, EC 4.2.1.1) are inhibited by sulfonamides, phenols, and coumarins. Polyamines such as spermine, spermidine, and many synthetic congeners are described to constitute a novel class of CA inhibitors (CAIs), interacting with the different CA isozymes with efficiency from the low nanomolar to millimolar range. The main structure?activity relationship for these CAIs have been delineated: the length of the molecule, number of amine moieties, and their functionalization are the main parameters controlling activity. The X-ray crystal structure of the CA II?spermine adduct allowed understanding of the inhibition mechanism. Spermine anchors to the nonprotein zinc ligand through a network of hydrogen bonds. Its distal amine moiety makes hydrogen bonds with residues Thr200 and Pro201, which further stabilize the adduct. Spermine binds differently compared to sulfonamides, phenols, or coumarins, rendering possible to develop CAIs with a diverse inhibition mechanism, profile, and selectivity for various isoforms.

Lipopolysaccharide sequestrants: Structural correlates of activity and toxicity in novel acylhomospermines

Lipopolysaccharides (LPS), otherwise termed "endotoxins", are outer membrane constituents of Gram-negative bacteria. Lipopolysaccharides play a key role in the pathogenesis of "septic shock", a major cause of mortality in the critically ill patient. Therapeutic options aimed at limiting downstream systemic inflammatory processes by targeting lipopolysaccharide do not exist at the present time. We have defined the pharmacophore necessary for small molecules to specifically bind and neutralize LPS and, using animal models of sepsis, have shown that the sequestration of circulatory LPS by small molecules is a therapeutically viable strategy. In this paper, the interactions of a series of acylated homologated spermine compounds with LPS have been characterized. The optimal acyl chain length for effective sequestration of LPS was identified to be C16 for the monoacyl compounds. The most promising of these compounds, 4e, binds LPS with an ED50 of 1.37 μM. Nitric oxide production in murine J774A.1 cells, as well as TNF-α in human blood, is inhibited in a dose-dependent manner by 4e at concentrations orders of magnitude lower than toxic doses. Administration of 4e to D-galactosamine-sensitized mice challenged with supralethal doses of LPS provided significant protection against lethality. Potent antiendotoxic activity, low toxicity, and ease of synthesis render this class of compounds candidate endotoxin-sequestering agents of potential significant therapeutic value.

Syntheses of a library of molecules on the marine natural product ianthelliformisamines platform and their biological evaluation

Ianthelliformisamines A-C are a novel class of bromotyrosine-derived antibacterial agents isolated recently from the marine sponge Suberea ianthelliformis. We have synthesized ianthelliformisamines A-C straightforwardly by the condensation of (E)-3-(3,5-dibromo-4-methoxyphenyl)acrylic acid and the corresponding Boc-protected polyamine followed by Boc-deprotection with TFA. Further, using this reaction protocol, a library of their analogues (39 analogues) has been synthesized by employing 3-phenylacrylic acid derivatives and Boc-protected polyamine chains through various combinations of these two fragments differing in phenyl ring substitution, double bond geometry or chain length of the central spacer of the polyamine chain (shown in red color). All the synthesized compounds (ianthelliformisamines A-C and their analogues) were screened for antibacterial activity against both Gram-negative (Escherichia coli) and Gram-positive (Staphylococcus aureus) strains. All synthetic analogues of ianthelliformisamine A showed bacterial growth inhibition against both strains (Escherichia coli and Staphylococcus aureus), having MIC values in the range of 117.8-0.10 μM, while none of the synthetic analogues of ianthelliformisamine C as well as the parent compound showed any detectable antibacterial activity. Interestingly, some of the synthetic analogues of ianthelliformisamines A and B exerted a bactericidal effect against both E. coli and S. aureus strains, decreasing viable bacterial count by 99% at concentrations as low as 2 × MIC. This journal is the Partner Organisations 2014.

Polyamine functionalized carbon nanotubes: Synthesis, characterization, cytotoxicity and siRNA binding

In this work we have synthesized a new series of cationic carbon nanotubes (CNTs) for siRNA binding. Both single- and multi-walled CNTs have been modified by addition or amidation reaction with short linear polyamine chains including putrescine, spermidin