68076-39-1

Usage

Uses

Used in Chemical Synthesis:
BIS-BOC-SPERMIDINE is used as a linker for chemical synthesis, particularly in the formation of complex molecules and bioconjugates. Its reactivity with various functional groups allows for the efficient creation of stable and functional molecular constructs.
Used in Pharmaceutical Industry:
BIS-BOC-SPERMIDINE is used as a building block for the development of new drugs and drug candidates. Its ability to form stable linkages with other molecules makes it a valuable component in the design and synthesis of novel therapeutic agents.
Used in Bioconjugation:
BIS-BOC-SPERMIDINE is used as a coupling agent for bioconjugation, a process that involves the attachment of biologically active molecules to other molecules, such as antibodies or enzymes. Its reactivity and Boc protection allow for the selective formation of covalent bonds under mild conditions, preserving the integrity of the biomolecules involved.
Used in Research and Development:
BIS-BOC-SPERMIDINE is used as a research tool for studying the interactions between various biomolecules and their potential applications in drug discovery, diagnostics, and therapeutics. Its versatility and reactivity make it a valuable compound for exploring new chemical and biological possibilities.

Upstream product

• 68102-93-2 {3-[tert-Butoxycarbonyl-(4-tert-butoxycarbonylamino-butyl)-amino]-propyl}-carbamic acid benzyl ester 
• 57294-38-9 N-(tert-butoxycarbonyl)-4-aminobutanoic acid 
• 95687-08-4 N¹-(3-chloropropyl)-N¹,N⁴-bis(t-butoxycarbonyl)butane-1,4-diamine 
• 90914-09-3 N⁽¹⁾-benzyl-N⁽⁴⁾-(tert-butyloxycarbonyl)-1,4-diaminobutane 
• 201211-59-8 tert-butyl {4-{benzyl[3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)propyl]amino}butyl}carbamate 
• 378785-51-4 [4-(benzylideneamino)butyl]carbamic acid tert-butyl ester 
• 75178-96-0 N-Boc-1,3-diaminopropane 
• 191277-07-3 tert-butyl {4-{[3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)propyl]amino}butyl}carbamate 
• 73371-96-7 2-<<(tert-butoxycarbonyl)oxy>imino>-2-phenylacetonitrile 
• 24424-99-5 di-tert-butyl dicarbonate 
• 68076-40-4 N¹-tert-butoxycarbonyl-N⁴-(2-cyanoethyl)-1,4-butanediamine 
• 1379342-99-0 N-Boc-diaminobutane 
• 4748-73-6 N-(cyanoethyl)-1,4-diaminobutane 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 

Downstream Products

• 70374-97-9 Z-Gly-di-Boc-Spe(3,4) 
• 133765-76-1 N¹-<<3-<3-4,N⁸-bis(tert-butoxycarbonyl)spermidinosuccinamido>benzene-1-carboxamido>benzen-1-yl>carbonyl>-N⁴,N⁸-bis(tert-butoxycarbonyl)spermidine 
• 77251-53-7 (E)-3-{4-[2-Benzyloxy-5-((E)-2-{3-[tert-butoxycarbonyl-(4-tert-butoxycarbonylamino-butyl)-amino]-propylcarbamoyl}-vinyl)-phenoxy]-3-methoxy-phenyl}-acrylic acid methyl ester 
• 95687-13-1 N¹-(4-acetoxycinnamoyl)-N⁴,N⁸-bis(t-butoxycarbonyl)spermidine 
• 95687-14-2 N¹-(4-acetoxy-3-methoxycinnamoyl)-N⁴,N⁸-bis(t-butoxycarbonyl)spermidine 
• 95687-16-4 N¹-(3,4-diacetoxycinnamoyl)-N⁴,N⁸-bis(t-butoxycarbonyl)spermidine 
• 95687-15-3 N¹-(4-acetoxy-3,5-dimethoxycinnamoyl)-N⁴,N⁸-bis(t-butoxycarbonyl)spermidine 
• 159719-44-5 tert-butyl N-<3-(benzamido)propyl>-N-<4-(<(tert-butyloxy)carbonyl>amino)butyl>carbamate 
• 160726-45-4 N¹-4<2-methoxy-5-(3-oxo-3-methoxy-1-propenyl)-phenoxy>-cinnamoyl-N²,N³-di-t-butoxycarbonyl-spermidine 
• 160726-39-6 N¹-4<2-methoxy-5-(3-oxo-3-t-butoxy-1-propenyl)-phenoxy>-cinnamoyl-N²,N³-di-t-butoxycarbonyl-spermidine 
• 69089-01-6 Di(tert-butyl)-N-(3-(<(E)-3-(4-hydroxyphenyl)prop-2-enoyl>amino)propyl)-N,N'-(butan-1,4-diyl)bis 
• 202979-78-0 (2'S)-N-(tert-butoxycarbonyl)phenylalanyl-N⁴,N⁸-bis(tert-butoxycarbonyl)spermidine 
• 322638-58-4 2-(benzyloxy)-N,N'-bis(3-{[(tert-butoxy)carbonyl](4-{[(tert-butoxy)carbonyl]amino}butyl)amino}propyl)-5-(tert-butyl)benzene-1,3-bis[propanamide] 
• 350609-84-6 3-[(2-benzyloxy)phenyl]-N-(3-{[(tert-butoxy)carbonyl](4-{[(tert-butoxy)carbonyl]amino}butyl)amino}propyl)propanamide 

Relevant academic research and scientific papers

Design, synthesis and anticancer activity of 2-amidomethoxy-1,4-naphthoquinones and its conjugates with Biotin/polyamine

In continuation with the previous work, a series of 5-hydroxy-2-amidomethoxy-1,4-naphthoquinones were prepared to establish the structure-activity relationship studies toward anticancer activity (IC50 in μM) against three cell lines; colo205 (colon adenocarcinoma), T47D (breast ductal carcinoma) and K562 (chronic myelogenous leukemia). Among the synthesized compounds, naphthoquinone amines, 5 (0.8; 0.6; 0.8), 14 (0.8; 0.6; 0.5) and the amine precursor, 4 (1.3; 0.3; 1.0) displayed potent anticancer activities. A tumor targeting drug delivery system was achieved by synthesizing the conjugate 6 (1.4; 0.5; 1.1) of naphthoquinone-amine 5 and Biotin which also proved its potency. Finally, to introduce polyamine conjugate, spermidine was attached with 2-amidomethoxy-1,4-naphthoquinone. The naphthoquinone-spermidine conjugate 27 (1.2; 1.7; 1.7) also retained the activity. Thus, potent naphthoquinone amines were explored and Biotin/polyamine conjugate was developed as tumor targeting drug delivery system.

A naphthalimide-polyamine conjugate preferentially accumulates in hepatic carcinoma metastases as a lysosome-targeted antimetastatic agent

Disseminated tumors lead to approximately 90% of cancer-associated deaths especially for hepatocellular carcinoma (HCC), indicating the imperative need of antimetastatic drugs and the ineffectiveness of current therapies. Recently polyamine derivatives have been identified as a promising prospect in dealing with metastatic tumors. Herein, a novel class of naphthalimide-polyamine conjugates 8a-8d, 13a-13c, 17 and 21 were synthesized and the mechanism was further determined. The polyamine conjugate 13b displayed remarkably elevated anti-tumor and anti-metastatic effects (76.01% and 75.02%) than the positive control amonafide (46.91% and 55.77%) at 5 mg/kg in vivo. The underlying molecular mechanism indicated that in addition to induce DNA damage by up-regulating p53 and γH2AX, 13b also targeted lysosome to modulate polyamine metabolism and function in a totally different way from that of amonafide. Furthermore, the HMGB1/p62/LC3II/LC3I and p53/SSAT/β-catenin pathways were mainly involved in the inhibition of 13b-induced HCC metastasis by targeting polyamine transporters (PTs) overexpressed in HCC. At last, 13b down-regulated the concentrations of Put, Spd and Spm by modulating polyamine metabolism key enzymes SSAT and PAO, which favored the suppression of fast growing tumor cells. Taken together, our study implies a promising strategy for naphthalimide conjugates to treat terminal cancer of HCC by targeting autophagy and tumor microenvironment with reduced toxicities and notable activities.

Naphthalene diimide-polyamine hybrids as antiproliferative agents: Focus on the architecture of the polyamine chains

Naphthalene diimides (NDIs) have been widely used as scaffold to design DNA-directed agents able to target peculiar DNA secondary arrangements endowed with relevant biochemical roles. Recently, we have reported disubstituted linear- and macrocyclic-NDIs that bind telomeric and non-telomeric G-quadruplex with high degree of affinity and selectivity. Herein, the synthesis, biological evaluation and molecular modelling studies of a series of asymmetrically substituted NDIs are reported. Among these, compound 9 emerges as the most interesting of the series being able to bind telomeric G-quadruplex (ΔTm = 29 °C at 2.5 μM), to inhibit the activity of DNA processing enzymes, such as topoisomerase II and TAQ-polymerase, and to exert antiproliferative effects in the NCI panel of cancer cell lines with GI50values in the micro-to nanomolar concentration range (i.e. SR cell line, GI50= 76 nM). Molecular mechanisms of cell death have been investigated and molecular modelling studies have been performed in order to shed light on the antiproliferative and DNA-recognition processes.

8-polyamido dihydromyricetin derivative and preparation method and application thereof

The present invention discloses an 8-polyamido dihydromyricetin derivative or a pharmaceutically acceptable hydrate and salt thereof including stereoisomers or tautomers thereof. The 8-polyamido dihydromyricetin derivative has anticancer activity and can be used for anticancer treatment drugs. The invention discloses a preparation method of the 8-polyamido dihydromyricetin derivative.

METHODS OF INCREASING THE CYTOTOXICITY OF CHEMOTHERAPEUTIC AGENTS WITH MULTISUBSTRATE INHIBITORS OF HISTONE, PROTEIN-LYS, POLYAMINE ACETYLATION, AND POLYAMINE METABOLISM

A method of treating cancer in a subject in need thereof, comprising administering to the subject a first amount of a compound of the HAT inhibitor of the following formula: wherein R is chosen from coenzyme A, (CH2)2NHCO(CH2)2NHCOR2; (CH2)2NHCOR3; (CH2)2NHCO(CH2)2NHCOR4; R1 is H, NH2, NH, N, and R1 can optionally cyclize with at least one other X2 to form a C3-8 membered ring containing C, O, S, or N; R2 is chosen from alkyl, cycloalkyl, aryl, heteroaryl; R3 is chosen from an alkyl, cycloalkyl, aryl, heteroaryl; R4 is chosen from CH(OH)C(CH3)2CH2)OCOR2; X1 is chosen from H or can cyclize with one other X2 or R1 to form a C3-8 membered ring containing C, O, S, or N; and X2 is chosen from C, N, NH, and can optionally cyclize with at least one other X2 or R1 to form a C3-8 membered ring containing C, O, S, or N; or a pharmaceutically acceptable salt or hydrate thereof, thereby treating the cancer.

Design, synthesis and in vitro antikinetoplastid evaluation of N-acylated putrescine, spermidine and spermine derivatives

A structure-activity relationship study on polyamine derivatives led to the synthesis and the determination of antikinetoplastid activity of 17 compounds. Among them, a spermidine derivative (compound 13) was specifically active in vitro against Leishmania donovani axenic amastigotes (IC50 at 5.4 μM; Selectivity Index >18.5) and a spermine derivative (compound 28) specifically active against Trypanosoma brucei gambiense (IC50 at 1.9 μM; Selectivity Index >52).

Design, synthesis and in vitro antikinetoplastid evaluation of N-acylated putrescine, spermidine and spermine derivatives

A structure-activity relationship study on polyamine derivatives led to the synthesis and the determination of antikinetoplastid activity of 17 compounds. Among them, a spermidine derivative (compound 13) was specifically active in vitro against Leishmania donovani axenic amastigotes (IC50 at 5.4 ??M; Selectivity Index >18.5) and a spermine derivative (compound 28) specifically active against Trypanosoma brucei gambiense (IC50 at 1.9 ??M; Selectivity Index >52).

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.

New ianthelliformisamine derivatives as antibiotic enhancers against resistant gram-negative bacteria

A series consisting of ianthelliformisamimes A, B, and C as well as its synthetic analogues was prepared in high chemical yield, from 27 to 91%, using peptide coupling as the key step, and the compounds were evaluated for their in vitro antibiotic enhancer properties against resistant Gram-negative bacteria and clinical isolates. The mechanism of action of one of these derivatives against Pseudomonas aeruginosa when combined with doxycycline was precisely evaluated utilizing bioluminescence to measure ATP efflux and fluorescence to evaluate membrane depolarization.

PLANT ACTIVATOR

A compound useful as a plant activator for activating an endogenous defense system of a plant to control disease damage is provided. A compound represented by the formula: (R3)NH—(CH2)4—N(R1)—(CH2)3—NH(R2) (one of R1 and R2 represents a linear C6-18 alkanoyl group or alkenoyl group, the other represents hydrogen atom or a protective group of amino group; and R3 represents hydrogen atom or a protective group of amino group).