抗菌、抗病毒双重活性的多金属氧酸盐药物的设计合成、结构和作用机理
摘要
多金属氧酸盐药物化学研究是目前该领域一个前沿热门课题。本论文在大量前期工作积累基础上提出了多酸药物合成的新思路:依据分子设计思想,将目前临床应用的药物分子组装到具有药物活性的多酸结构中,形成具有双活性中心的新的超分子化合物。研究表明,一些这样的超分子对流感病毒及多种病菌显示出强的抑制活性。渴望成为具有抗菌、抗病毒双重活性的新型多酸药物。
一、化合物的合成及结构
1.合成了含有临床药物吗啉胍、咖啡碱、金刚烷胺、5-氟胞嘧啶、异烟肼等14个新多金属氧酸盐超分子化合物,并得到其中4个化合物的晶体结构,分别是:含有吗啉胍的十钒酸盐化合物1, (C6H14N5O)4 H2V10O28·9H2O和化合物2 ,(C6H14N5O)6V10O28·4H2O ,这两个化合物均属单斜晶系,其中化合物1为P21/c空间群, 晶胞参数a = 1.3396 (1), b = 1.4826 (1), c = 1.7135 (1), ? = 111.450 (3) o, V = 3.1675 (4) nm3, Z = 2;化合物2为P21/n空间群, a = 1.1699 (1), b = 2.4079 (1), c = 1.3132 (1) nm, ? = 91.635 (2) o, V = 3.6978 (4) nm3, Z = 2。化合物3由咖啡碱与十钒酸根自组装形成,分子式为(NH4)2(C8H10N4O2)4H4V10O28·2H2O, 单斜晶系,P21/n空间群,a = 1.5801(1),b = 1.2914 (1),c = 1.5913 (2) nm,β= 113.55o,V=2.9764 (5) nm3,Z=2。化合物4为十钒酸根与金刚烷胺形成的化合物,分子式为 (C10H18N)4H2V10O28·12H2O,三斜晶系,Pī空间群,a = 1.31437 (5), b = 1.4401 (1), c = 1.8865(1) nm, α = 105.920 (3), β = 99.578(2) o , γ = 90.082 (2)o, V=3.3819 (3)nm3, Z= 2。
2.以硫脲为还原剂分别与Keggin型钼磷酸、钼硅酸反应,得到2个新的杂多蓝单晶:化合物(C2H4N4S3)2 H5PMo10VIMo2VO40·6H2O(6)和 (CH4NS)0.5(C2H4N4S2)(C2H4N4S3)0.5H6SiMo10VI Mo2VO40·4H2O(7)。其中化合物6属单斜晶系,C2/c空间群,a =2.1746(4), b=1.1177(2), c= 2.0931(4) nm, β =99.59 (3) o, V=4.8871 nm3, Z=4。化合物7属三斜晶系,Pī空间群,a =1.21219(7), b=1.12831(8), c= 1.64655(10) nm, α = 97.2380 (10), β =95.5600(10) , γ = 113.6360 (10)o, V=2.1766 (2)nm3, Z= 2。通过1H NMR和13C NMR表征两个化合物的谱图结果证实了X-ray单晶衍
射解析的结果。
3.化合物(NH4)4(DMSO)4H2V10O28(5)的晶体结构在常温水溶液中得到,属单斜晶系,P21/n空间群,a= 1.0719(2), b=0.9658(2), c=2.0171(4) nm, β=98.42(3) °, V= 2.0657(7) nm3, Z= 2。该晶体沿a或b轴晶胞堆积排列中多阴离子是彼此平行且方向一致的,而沿(1,1,0)平面可以看出多个十钒酸根离子的交错层状排列,DMSO分子之间通过与NH4+的氢键连接呈现出链结构。
二、抗菌、抗病毒活性
1.研究表明:临床药物吗啉胍、咖啡碱、金刚烷胺与同多十钒-氧簇自组装超分子化合物(分别为1,2,3和4)具有广谱的抗菌活性。特别是对肺炎链球菌有强的抑制活性,并且化合物1,2对耐甲氧西林金黄葡萄球菌(MRSA)和耐甲氧西林表皮葡萄球菌(MRSE)也显示出强的抗菌活性。化合物3对革兰氏阳性菌(肺炎链球菌)和革兰氏阴性菌(绿脓杆菌)都有一定抑制效果,但选择性不明显。而化合物4能选择性抑制大肠杆菌。
2.硫脲为还原剂得到的两个杂多蓝晶体(C2H6N4S3)2 H5PMo10VIMo2VO40·6H2O(6)和 (CH4NS)0.5(C2H6N4S2) (C2H6N4S3)0.5H6
SiMo10VI Mo2VO40·4H2O(7)以及异烟肼、吗啉胍与LnW10O369-自组装化合物(9和10)与?-Lactam抗生素甲氧西林联合用药时,对MRSA协同效应明显。进一步研究表明,抑制?-内酰胺酶的产生可能是导致这类化合物与?-Lactam antibiotics联合用药时产生协同效应的原因。
3.上述化合物6,7对流感病毒A, B也显示出明显的抑制活性。
The research on medicinal chemistry of polyoxometalates is one of the highlights in this field currently. This paper present a new synthesis idea based on the previous researches: according to the standpoint of molecular design, introducing the clinical drugs into the framework of pharmaceutical activity polyoxometalates to synthesize novel supramolecular compounds with bi-active centers. The investigation indicated that some of these compounds showed strong inhibitory action to influenza virus and many other bacteria. They are expected to be explored novel polyoxometalate medicines with antibacterial and anti-viral bi-activity.
Synthesis and structure of the compounds
1.1 Fourteen polyoxometalate supramolecular compounds containing moroxydine, caffeine, amantadine, 5-Fc and isoniazid were prepared , and four of them have been characterized by X-ray structure analysis: (C6H14N5O)4H2V10O28·9H2O (1) and (C6H14N5O)6V10O28·4H2O (2) are constructed from decavanadate and moroxydine. Compound 1 crystallizes in the monoclinic crystal system, space group P21/c, a = 1.3396 (1), b = 1.4826 (1), c = 1.7135 (1), ? = 111.450 (3) o, V = 3.1675 (4) nm3, Z = 2;Compound 2, monoclinic, space group P21/n, a = 1.1699 (1), b = 2.4079 (1), c = 1.3132 (1) nm, ? = 91.635 (2) o, V = 3.6978 (4) nm3, Z = 2。The self-assembly by devanadate and caffeine, Compound 3, with the foumula (NH4)2(C8H10N4O2)4H4V10O28·2H2O, monoclinic crystal system, space group P21/n, a = 1.5801(1),b = 1.2914 (1),c = 1.5913 (2),β= 113.55o,V=2.9764 (5) nm3,Z=2。Compound 4 with the molecular formula (C10H18N)4H2V10O28·12H2O (4) consisted of amantadine and devanadate, triclinic crystal system, space group Pī, a = 1.31437 (5), b = 1.4401 (1), c = 1.8865(1) nm, α = 105.920 (3), β = 99.578(2) o , γ = 90.082 (2)o, V=3.3819 (3)nm3, Z= 2。
1.2 Thiourea, as a reducing reagent, reacted with Keggin-
phosphmolybdic acid and silicomolybdic acid, respectively to form two novel heteropolybule crystals : (C2H4N4S3)2 H5PMo10VIMo2VO40·6H2O(6)and (CH4NS)0.5(C2H4N4S2)(C2H4N4S3)0.5H6SiMo10VI Mo2VO40·4H2O(7). Compound 6 crystallizes in the monoclinic crystal system, space group C2/c with a =2.1746(4), b =1.1177(2), c = 2.0931(4) nm, β =99.59 (3) o, V = 4.8871 nm3, Z=4。Compound 7 crystallizes in the triclinic crystal system, space group Pīwith a = 1.21219(7), b = 1.12831(8), c = 1.64655(10) nm, α = 97.2380 (10), β = 95.5600(10) , γ = 113.6360 (10)o, V =2.1766 (2)nm3, Z = 2。These two crystal structures determined by X-ray diffraction could be confirmed by the analysis of 1H NMR and 13C NMR spectra.
1.3 The crystal structure of (NH4)4(DMSO)4H2V10O28 (5) was obtained in aqueous solution at room temperature, crystallized in monoclinic crystal system, space group P21/n , a = 1.0719(2), b =0.9658(2), c = 2.0171(4) nm, β=98.42(3) °, V= 2.0657(7) nm3, Z = 2。In the arrangement of unit-cell packing along a or b axis, the polyanions were parallel and in an identical direction, while onto (1,1,0) plane many decavanadate anions arrange interveined to form layers. In this structure DMSO molecules linked through extensive hydrogen bonds with ammonium to form the chain structure.
Antibacterial and anti-viral activity
2.1. The investigation indicated that clinical drugs such as moroxydine, caffeine, amantadine could be incorporated into decavanadium cluster to form supramolecular compounds (marked 1, 2, 3 and 4) by self-assembly. The novel compounds showed broad-spectrum antibacterial activity, especially had strong inhibition against Streptococcus Pneumoniae (S. Pneumoniae). Simultaneously, Compound 1 and 2 exhibited strong antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) and methicillin-resistant Staphylococcus epidermids (MRSE). Compound 3 showed inhibition to gram-positive strain (S. Pneumoniae) and gram-negative strain (P. aeruginosa) but the selectivity is not distinct, while
compound 4 could inhibit E.Coli selectively.
2.2 The self-assembly constructed from LaW10O369- and isoniazid (8), LaW10O369- and moroxydine (9) and th
一、化合物的合成及结构
1.合成了含有临床药物吗啉胍、咖啡碱、金刚烷胺、5-氟胞嘧啶、异烟肼等14个新多金属氧酸盐超分子化合物,并得到其中4个化合物的晶体结构,分别是:含有吗啉胍的十钒酸盐化合物1, (C6H14N5O)4 H2V10O28·9H2O和化合物2 ,(C6H14N5O)6V10O28·4H2O ,这两个化合物均属单斜晶系,其中化合物1为P21/c空间群, 晶胞参数a = 1.3396 (1), b = 1.4826 (1), c = 1.7135 (1), ? = 111.450 (3) o, V = 3.1675 (4) nm3, Z = 2;化合物2为P21/n空间群, a = 1.1699 (1), b = 2.4079 (1), c = 1.3132 (1) nm, ? = 91.635 (2) o, V = 3.6978 (4) nm3, Z = 2。化合物3由咖啡碱与十钒酸根自组装形成,分子式为(NH4)2(C8H10N4O2)4H4V10O28·2H2O, 单斜晶系,P21/n空间群,a = 1.5801(1),b = 1.2914 (1),c = 1.5913 (2) nm,β= 113.55o,V=2.9764 (5) nm3,Z=2。化合物4为十钒酸根与金刚烷胺形成的化合物,分子式为 (C10H18N)4H2V10O28·12H2O,三斜晶系,Pī空间群,a = 1.31437 (5), b = 1.4401 (1), c = 1.8865(1) nm, α = 105.920 (3), β = 99.578(2) o , γ = 90.082 (2)o, V=3.3819 (3)nm3, Z= 2。
2.以硫脲为还原剂分别与Keggin型钼磷酸、钼硅酸反应,得到2个新的杂多蓝单晶:化合物(C2H4N4S3)2 H5PMo10VIMo2VO40·6H2O(6)和 (CH4NS)0.5(C2H4N4S2)(C2H4N4S3)0.5H6SiMo10VI Mo2VO40·4H2O(7)。其中化合物6属单斜晶系,C2/c空间群,a =2.1746(4), b=1.1177(2), c= 2.0931(4) nm, β =99.59 (3) o, V=4.8871 nm3, Z=4。化合物7属三斜晶系,Pī空间群,a =1.21219(7), b=1.12831(8), c= 1.64655(10) nm, α = 97.2380 (10), β =95.5600(10) , γ = 113.6360 (10)o, V=2.1766 (2)nm3, Z= 2。通过1H NMR和13C NMR表征两个化合物的谱图结果证实了X-ray单晶衍
射解析的结果。
3.化合物(NH4)4(DMSO)4H2V10O28(5)的晶体结构在常温水溶液中得到,属单斜晶系,P21/n空间群,a= 1.0719(2), b=0.9658(2), c=2.0171(4) nm, β=98.42(3) °, V= 2.0657(7) nm3, Z= 2。该晶体沿a或b轴晶胞堆积排列中多阴离子是彼此平行且方向一致的,而沿(1,1,0)平面可以看出多个十钒酸根离子的交错层状排列,DMSO分子之间通过与NH4+的氢键连接呈现出链结构。
二、抗菌、抗病毒活性
1.研究表明:临床药物吗啉胍、咖啡碱、金刚烷胺与同多十钒-氧簇自组装超分子化合物(分别为1,2,3和4)具有广谱的抗菌活性。特别是对肺炎链球菌有强的抑制活性,并且化合物1,2对耐甲氧西林金黄葡萄球菌(MRSA)和耐甲氧西林表皮葡萄球菌(MRSE)也显示出强的抗菌活性。化合物3对革兰氏阳性菌(肺炎链球菌)和革兰氏阴性菌(绿脓杆菌)都有一定抑制效果,但选择性不明显。而化合物4能选择性抑制大肠杆菌。
2.硫脲为还原剂得到的两个杂多蓝晶体(C2H6N4S3)2 H5PMo10VIMo2VO40·6H2O(6)和 (CH4NS)0.5(C2H6N4S2) (C2H6N4S3)0.5H6
SiMo10VI Mo2VO40·4H2O(7)以及异烟肼、吗啉胍与LnW10O369-自组装化合物(9和10)与?-Lactam抗生素甲氧西林联合用药时,对MRSA协同效应明显。进一步研究表明,抑制?-内酰胺酶的产生可能是导致这类化合物与?-Lactam antibiotics联合用药时产生协同效应的原因。
3.上述化合物6,7对流感病毒A, B也显示出明显的抑制活性。
The research on medicinal chemistry of polyoxometalates is one of the highlights in this field currently. This paper present a new synthesis idea based on the previous researches: according to the standpoint of molecular design, introducing the clinical drugs into the framework of pharmaceutical activity polyoxometalates to synthesize novel supramolecular compounds with bi-active centers. The investigation indicated that some of these compounds showed strong inhibitory action to influenza virus and many other bacteria. They are expected to be explored novel polyoxometalate medicines with antibacterial and anti-viral bi-activity.
Synthesis and structure of the compounds
1.1 Fourteen polyoxometalate supramolecular compounds containing moroxydine, caffeine, amantadine, 5-Fc and isoniazid were prepared , and four of them have been characterized by X-ray structure analysis: (C6H14N5O)4H2V10O28·9H2O (1) and (C6H14N5O)6V10O28·4H2O (2) are constructed from decavanadate and moroxydine. Compound 1 crystallizes in the monoclinic crystal system, space group P21/c, a = 1.3396 (1), b = 1.4826 (1), c = 1.7135 (1), ? = 111.450 (3) o, V = 3.1675 (4) nm3, Z = 2;Compound 2, monoclinic, space group P21/n, a = 1.1699 (1), b = 2.4079 (1), c = 1.3132 (1) nm, ? = 91.635 (2) o, V = 3.6978 (4) nm3, Z = 2。The self-assembly by devanadate and caffeine, Compound 3, with the foumula (NH4)2(C8H10N4O2)4H4V10O28·2H2O, monoclinic crystal system, space group P21/n, a = 1.5801(1),b = 1.2914 (1),c = 1.5913 (2),β= 113.55o,V=2.9764 (5) nm3,Z=2。Compound 4 with the molecular formula (C10H18N)4H2V10O28·12H2O (4) consisted of amantadine and devanadate, triclinic crystal system, space group Pī, a = 1.31437 (5), b = 1.4401 (1), c = 1.8865(1) nm, α = 105.920 (3), β = 99.578(2) o , γ = 90.082 (2)o, V=3.3819 (3)nm3, Z= 2。
1.2 Thiourea, as a reducing reagent, reacted with Keggin-
phosphmolybdic acid and silicomolybdic acid, respectively to form two novel heteropolybule crystals : (C2H4N4S3)2 H5PMo10VIMo2VO40·6H2O(6)and (CH4NS)0.5(C2H4N4S2)(C2H4N4S3)0.5H6SiMo10VI Mo2VO40·4H2O(7). Compound 6 crystallizes in the monoclinic crystal system, space group C2/c with a =2.1746(4), b =1.1177(2), c = 2.0931(4) nm, β =99.59 (3) o, V = 4.8871 nm3, Z=4。Compound 7 crystallizes in the triclinic crystal system, space group Pīwith a = 1.21219(7), b = 1.12831(8), c = 1.64655(10) nm, α = 97.2380 (10), β = 95.5600(10) , γ = 113.6360 (10)o, V =2.1766 (2)nm3, Z = 2。These two crystal structures determined by X-ray diffraction could be confirmed by the analysis of 1H NMR and 13C NMR spectra.
1.3 The crystal structure of (NH4)4(DMSO)4H2V10O28 (5) was obtained in aqueous solution at room temperature, crystallized in monoclinic crystal system, space group P21/n , a = 1.0719(2), b =0.9658(2), c = 2.0171(4) nm, β=98.42(3) °, V= 2.0657(7) nm3, Z = 2。In the arrangement of unit-cell packing along a or b axis, the polyanions were parallel and in an identical direction, while onto (1,1,0) plane many decavanadate anions arrange interveined to form layers. In this structure DMSO molecules linked through extensive hydrogen bonds with ammonium to form the chain structure.
Antibacterial and anti-viral activity
2.1. The investigation indicated that clinical drugs such as moroxydine, caffeine, amantadine could be incorporated into decavanadium cluster to form supramolecular compounds (marked 1, 2, 3 and 4) by self-assembly. The novel compounds showed broad-spectrum antibacterial activity, especially had strong inhibition against Streptococcus Pneumoniae (S. Pneumoniae). Simultaneously, Compound 1 and 2 exhibited strong antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) and methicillin-resistant Staphylococcus epidermids (MRSE). Compound 3 showed inhibition to gram-positive strain (S. Pneumoniae) and gram-negative strain (P. aeruginosa) but the selectivity is not distinct, while
compound 4 could inhibit E.Coli selectively.
2.2 The self-assembly constructed from LaW10O369- and isoniazid (8), LaW10O369- and moroxydine (9) and th
引文
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