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Synthesis, characterization, and radioprotective activity of ?,?-unsaturated aryl sulfone analogs and their Tempol conjugates.

ABSTRACT: Some novel ?,?-unsaturated aromatic sulfone analogs (5a-5m) and their Tempol conjugates (6a-6e) have been synthetically prepared, characterized and evaluated for their radioprotective activity under ?-ray radiation. The Tempol conjugates were characterized by X-ray single crystal diffraction. In vitro studies showed that 5a, 5b and 6b had superior activities to Ex-Rad pre-treated before 5 Gy irradiation, and 5a, 6a and 6b had better activities than Ex-Rad after 5 Gy irradiation, while 5a, 6a and 6b exhibited both prophylactic and mitigation effects, indicating the advantage of combining ?,?-unsaturated aromatic sulfones with Tempol nitroxide. Both p53 and phospho-p53 levels were significantly lower in compound-treated cells than those in untreated irradiated cells. The conjugates offer an improved radioprotective ability, which is an advantage in the treatment protocol.

SUBMITTER: Zhou N

PROVIDER: S-EPMC6072343 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature

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Synthesis, characterization, and radioprotective activity of α,β-unsaturated aryl sulfone analogs and their Tempol conjugates.

Zhou Nan N Feng Tian T Shen Xin X Cui Jiahui J Wu Rangxin R Wang Libin L Wang Siwang S Zhang Shengyong S Chen Hui H

MedChemComm 20170308 5

Some novel α,β-unsaturated aromatic sulfone analogs (5a-5m) and their Tempol conjugates (6a-6e) have been synthetically prepared, characterized and evaluated for their radioprotective activity under γ-ray radiation. The Tempol conjugates were characterized by X-ray single crystal diffraction. In vitro studies showed that 5a, 5b and 6b had superior activities to Ex-Rad pre-treated before 5 Gy irradiation, and 5a, 6a and 6b had better ...[more]

PMID: 30108819

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Project description:Three symmetrical bis-aryl-α,β-unsaturated ketone derivatives, 2,6-di((E)-benzylidene)-cyclohexan-1-one (DBC), 2,6-bis((E)-4-chlorobenzylidene)cyclohexan-1-one (BCC), and (1E,1'E,4E,4'E)-5,5'-(1,4-phenylene)bis(2-methyl-1-phenylpenta-1,4-dien-3-one) (PBMP), have been prepared using the aldol condensation approach toward ketones having two enolizable sites. The structures of DBC, BCC, and PBMP have been resolved via spectrometric methods. Moreover, the crystal structure of PBMP is determined by the single-crystal X-ray diffraction (SC-XRD) technique, which revealed that the PBMP molecular assembly is stabilized by the intermolecular C-H···O bonding and C-O···π and weak T-shaped offset π···π stacking interactions. The Hirshfeld surface analysis (HSA) of the PBMP crystal structure was performed as well, and the results were compared with the results of DBC and BCC. The density functional theory (DFT) study results revealed that the longer conjugated molecule of PBMP has smaller but still quite significant HOMO-LUMO gaps compared to the smaller molecules of BCC and DBC. The natural population analysis (NPA) and natural bonding orbital (NBO) analysis were performed. Accordingly, the hydrogen bonding and dipole-dipole interactions stabilize the crystal structures of these compounds. Additionally, the NBO analysis showed numerous high-energy stabilizing interactions for the PBMP compound due to the presence of numerous delocalized and relatively easily polarizable π-electrons, thus implying its significant thermodynamic stability. According to the global reactivity parameter (GRP) analysis, the compounds BCC and DBC are relatively stable in redox processes and have high thermodynamic stability and relatively lower reactivity in general. The molecular electrostatic potential (MEP) analysis results imply potential formation of the intermolecular hydrogen bonding and dispersion interactions, which stabilizes the crystal structures of these compounds.

Dataset Information

Synthesis, characterization, and radioprotective activity of ?,?-unsaturated aryl sulfone analogs and their Tempol conjugates.

Publications

Synthesis, characterization, and radioprotective activity of α,β-unsaturated aryl sulfone analogs and their Tempol conjugates.

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