Dataset Information

Molecular recognition. 1. Crystal structures of hexaazamacrocyclic amines containing p-xylylene spacers and their adducts with acids.

ABSTRACT: The macrocyclic amine, 1,5,9,18,22,26-hexaaza [11.11]-p-cyclophane (1) contains two dipropylenetriamine units which make the molecule highly basic. Owing to this basicity, 1 can be highly protonated in acidic media and can form supramolecular assemblies with different anions. Two new supramolecular structures arise from self-assembly of the salt of 1 with fumaric acid and of the N-methyl derivative of 1.

SUBMITTER: Borowiak T

PROVIDER: S-EPMC1399464 | biostudies-other | 2005

REPOSITORIES: biostudies-other

ACCESS DATA

Publications

Molecular recognition. 1. Crystal structures of hexaazamacrocyclic amines containing p-xylylene spacers and their adducts with acids.

Borowiak Teresa T Dutkiewicz Grzegorz G Dutkiewicz Grzegorz G Kubicki Maciej M Pietraszkiewicz Marek M Gil Agnieszka A Mattes Rainer R

Beilstein journal of organic chemistry 20051209

The macrocyclic amine, 1,5,9,18,22,26-hexaaza [11.11]-p-cyclophane (1) contains two dipropylenetriamine units which make the molecule highly basic. Owing to this basicity, 1 can be highly protonated in acidic media and can form supramolecular assemblies with different anions. Two new supramolecular structures arise from self-assembly of the salt of 1 with fumaric acid and of the N-methyl derivative of 1. ...[more]

PMID: 16551374

Similar Datasets

Project description:Arylamines (AAs) and heterocyclic aromatic amines (HAAs) are structurally related carcinogens formed during the combustion of tobacco or cooking of meat. They undergo cytochrome P450 mediated N-hydroxylation to form metabolites which bind to DNA and lead to mutations. The N-hydroxylated metabolites of many AAs also can undergo a co-oxidation reaction with oxy-hemolgobin (HbO2) to form methemoglobin (met-Hb) and the arylnitroso intermediates, which react with the ?-Cys(93) chain of Hb to form Hb-arylsulfinamide adducts. The biochemistry of arylamine metabolism has been exploited to biomonitor certain AAs through their Hb arylsulfinamide adducts in humans. We examined the reactivity of HbO2 with the N-hydroxylated metabolites of 4-aminobiphenyl (ABP, HONH-ABP), aniline (ANL, HONH-ANL), and the HAAs 2-amino-9H-pyrido[2,3-b]indole (A?C, HONH-A?C), 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP, HONH-PhIP), and 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx, HONH-MeIQx). HONH-ABP, HO-ANL, and HONH-A?C induced methemoglobinemia and formed Hb sulfinamide adducts. However, HONH-MeIQx and HONH-PhIP did not react with the oxy-heme complex, and met-Hb formation and chemical modification of the ?-Cys(93) residue were negligible. Molecular modeling studies showed that the distances between the H-ON-AA or H-ON-HAA substrates and the oxy-heme complex of HbO2 were too far away to induce methemoglobinemia. Different conformational changes in flexible helical and loop regions around the heme pocket induced by the H-ON-AA or H-ON-HAAs may explain the different proclivities of these chemicals to induce methemoglobinemia. Hb-Cys(93?) sulfinamide and sulfonamide adducts of ABP, ANL, and A?C were identified, by Orbitrap MS, following the proteolysis of Hb with trypsin, Glu-C, or Lys-C. Hb sulfinamide and sulfonamide adducts of ABP were identified in the blood of mice exposed to ABP, by Orbitrap MS. This is the first report of the identification of intact Hb sulfinamide adducts of carcinogenic AAs in vivo. The high reactivity of HONH-A?C with HbO2 suggests that the Hb sulfinamide adduct of A?C may be a promising biomarker of exposure to this HAA in humans.

Dataset Information

Molecular recognition. 1. Crystal structures of hexaazamacrocyclic amines containing p-xylylene spacers and their adducts with acids.

Publications

Molecular recognition. 1. Crystal structures of hexaazamacrocyclic amines containing p-xylylene spacers and their adducts with acids.

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets