90359-20-9

Upstream product

• 3626-00-4 ethylenediaminetetraacetic acid tetraethyl ester 
• 60-00-4 ethylenediaminetetraacetic acid 

Downstream Products

• 508201-36-3 {[({[3-(acridin-9-ylamino)-5-hydroxymethyl-phenylcarbamoyl]-methyl}-carbamoyl)-methyl]-[2-(bis-ethoxycarbonylmethyl-amino)-ethyl]-amino}-acetic acid ethyl ester 
• 508201-37-4 {({3-[3-acetoxymethyl-5-(acridin-9-ylamino)-phenylcarbamoyl]-propylcarbamoyl}-methyl)-[2-(bis-ethoxycarbonylmethyl-amino)-ethyl]-amino}-acetic acid ethyl ester 
• 767349-51-9 5-(2-{[2-(bis-ethoxycarbonylmethyl-amino)-ethyl]-ethoxycarbonylmethyl-amino}-acetylamino)-2-hydroxy-benzoic acid 
• 794488-25-8 5-(2-{[2-(bis-carboxymethyl-amino)-ethyl]-carboxymethyl-amino}-acetylamino)-2-hydroxy-benzoic acid 
• 776297-88-2 5'-O-(4,4'-dimethoxytrityl)-N⁴-[trans-4-(2-{[2-bis(ethoxycarbonylmethylamino)ethyl]ethoxycarbonylmethylamino}acetylamino)cyclohexyl]-2'-deoxycytidine 
• 776297-94-0 5'-O-(4,4'-dimethoxytrityl)-N⁴-[6-(2-{[2-bis(ethoxycarbonylmethylamino)ethyl]ethoxycarbonylmethylamino}acetylamino)hexyl]-2'-deoxycytidine 
• 776297-93-9 5'-O-(4,4'-dimethoxytrityl)-N⁴-[2-(2-{[2-bis(ethoxycarbonylmethylamino)ethyl]ethoxycarbonylmethylamino}acetylamino)ethyl]-2'-deoxycytidine 
• 776297-86-0 N⁴-[trans-4-(2-{[2-bis(ethoxycarbonylmethylamino)ethyl]ethoxycarbonylmethylamino}acetylamino)cyclohexyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-deoxycytidine 
• 776297-87-1 N⁴-[trans-4-(2-{[2-bis(ethoxycarbonylmethylamino)ethyl]ethoxycarbonylmethylamino}acetylamino)cyclohexyl]-2'-deoxycytidine 

Relevant academic research and scientific papers

NOVEL CHELATOR AND USE THEREOF

The present invention relates to dimeric pentadentate chelators with exceptionally strong binding of metal ions, for detection, immobilization and purification of biomolecules. Dimeric chelators offer a cooperativity of binding of two adjacent immobilized metal ions simultaneously to a histidine-tagged biomolecule, which gives advantageous properties regarding strength of binding compared to a corresponding monomer chelator. In addition, a dimer increases the selectivity (ease of separation) against non-tagged biomolecules with low metal-ion affinity. The dimeric pentadentate chelator according to the invention has the following general formula (I) wherein Sc is a scaffold or a connecting structure that contains at least two functional groups enabling coupling of two pentadentate chelators (PD), and PD is a pentadentate chelator having the formula (II).

Synthesis of monomeric 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. In the presence of ascorbate a reduction of the phage-titer of MS2 phages by several logarithmic decades was achieved.

Synthesis of pathogen inactivating 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 starting from 1,ω-alkyldiamines. As shown in model screenings, in the presence of ascorbic acid the Fe-complexes of these compounds reduced the phage-titer of MS2-phages by several logarithmic decades.

Selective Monohydrolysis of Esters of Polyaminocarboxylic acids using Pig Liver Esterase

Esters of a number of α- and β-polyaminocarboxylic acids have been selectively hydrolyzed to the corresponding monoacids using pig liver esterase in moderate to good yields.Foe example, the tetraethyl ester of EDTA is hydrolyzed to the corresponding monoacid using PLE at pH 8 in 4.5 hours in 86percent yield.Enzymatic hydrolysis provides ready access to this important class of synthetic intermediates.

Bifunctional molecules having a DNA intercalator or DNA groove binder linked to ethylene diamine tetraacetic acid, their preparation and use to cleave DNA

Bifunctional molecules having a DNA intercalator or DNA groove binder linked to ethylene diamine tetraacetic acid such as compounds having the formula: STR1 wherein R is methyl or ethyl. Also, the method of cleaving DNA by contact with one of the above-identified molecules in the presence of ferrous ion and oxygen. The process of preparing said molecules by the reaction of P-carboxy methidium halide, p-carboxy ethidium halide, or other DNA intercalator or DNA groove binder with 1-3-diaminopropane followed by condensation with ethylenediamine tetraacetic acid. Distamycin-EDTA.Fe(II)(DE.FE(II)) contains EDTA attached to the amino terminus of the groove binder tripeptide (tris-N-methylpyrrolecarboxamide). De.Fe(II) cleaves DNA contiguous to a five base pair A+T rich sequence. This is a novel and unique molecule and superior in sequence specificity to the naturally occurring antitumor compound used in man, bleomycin which cleaves DNA at a two base pair recognition site. EDTA-distamycin-Fe(II)(ED.Fe(II)) contains EDTA attached to the carboxy terminus of the groove binder tripeptide, tris-N-methylpyrrolecarboxamide. ED.Fe(II) cleaves DNA contiguous to a five base pair A+T rich sequence. Penta-N-methylpyrrolecarboxamide-EDTA.Fe(II)(P5E.Fe(II)) cleaves on opposite strands at the six base pair recognition level in a catalytic reaction. This is the first designed synthetic molecule that approximates the double strand sequence specific cleavage of DNA(4-6 bp recognition level) by the natural substance restriction enzymes, tools which make possible recombinant DNA manipulations. P5E.Fe(II) cuts DNA at sequences not available by the naturally occurring restriction enzymes. The dimers, bis(EDTA-distamycin.Fe(II)) and EDTA-bisdistamycin.Fe(II) which double strand cleave DNA at the eight base pair recognition level (A+T rich).

DNA AFFINITY CLEAVING SEQUENCE SPECIFIC CLEAVAGE OF DNA BY DISTAMYCIN-EDTA*Fe(II) AND EDTA-DISTAMYCIN*Fe(II)

The attachment of EDTA*Fe(II) to distamycin changes the sequence specific DNA binding antibiotic into a sequence specific DNA cleaving molecule.We report the synthesis of EDTA-distamycin (ED) which has the metal chelator, EDTA, tethered to the carboxy terminus of the N-methylpyrrole tripeptide moiety of the antibiotic, distamycin.EDTA-distamycin*Fe(II) (ED*Fe(II)) at 1E-6M concentration efficiently cleaves pBR322 DNA (1E-5M in base pairs) in the presence of oxygen and dithiothreitol (DTT).Using Maxam-Gilbert sequencing gel analyses, we find that ED*Fe(II) affords DNA cleavage patterns of unequal intensity covering two to four contiguous base pairs adjacent to a five base pair site consisting of adenines (A) and thymines (T).The multiple cleavages at each site might be evidence for a diffusible oxidizing species, perhaps hydroxyl radical.The unequal intensity of cleavage on each side of the A + T site permit assignment of major and minor orientations of the tripeptide binding unit.A comparison of the cleavage specificity of ED*Fe(II) with distamycin-EDTA*Fe(II), (DE*Fe(II)) which has EDTA*Fe(II) attached to the amino terminus of the N-methylpyrrole tripeptide, shows DNA cleavage patterns at the same sites but with intensities of opposite polarity.Maxam-Gilbert sequencing gel analysis of the DNA cleavage patterns by ED*Fe(II) and DE*Fe(II) on both DNA strands of a 381 base pair restriction fragment reveals asymmetric DNA cleavage patterns.Cleavage is shifted to the 3' side of each DNA strand.A model consistent with this cleavage pattern indicates one preferred binding site for ED*Fe(II) and DE*Fe(II) is 3'-TTTAA-5' with the "amino end" of the tripeptide oriented to the 3' end of the thyamine rich strand.This "DNA affinity cleavage" method which consists of attaching cleaving functions to DNA binding molecules followed by DNA cleavage pattern analyses using Maxam-Gilbert sequencing gels may be a useful direct method for determining the binding site and orientation of small molecules on native DNA.