CN106132961A - 是sod模拟物的金属络合物作为食品试剂和作为化妆品的应用 - Google Patents
是sod模拟物的金属络合物作为食品试剂和作为化妆品的应用 Download PDFInfo
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Abstract
本发明涉及是式(1)的由大环聚氮杂环吡啶烷化合物制得的超氧化物歧化酶(SOD)酶的模拟物的金属络合物作为食品试剂的应用，并且还涉及其作为化妆品的应用。
Description
发明领域
本发明涉及模拟酶超氧化物歧化酶(SOD)的金属络合物作为食品试剂的应用以及它们作为化妆品的应用，所述金属络合物记述在专利ES2355784中，并且由大环聚氮杂环吡啶烷化合物获得。
技术状况
抗氧化剂在皮肤保护和修复机制中起重要作用。它们可以作为食品或作为食品补充物消费，或可以作为局部制剂涂覆在皮肤上。酶超氧化物歧化酶(SOD)属于最重要的一组天然抗氧化物质。
现有技术反映SOD在机体中行使重要功能，诸如，例如，针对细胞氧化应激进行保护和针对炎性或变性过程进行保护。由SOD酶催化的超氧化物自由基(O2 -)成为氧和过氧化氢(H2O2)的歧化反应使得该酶在对暴露于氧的大部分细胞的抗氧化防御中是非常重要的。因此，SOD保护细胞免于O2 -自由基的有害反应。
当SOD活性失效时，氧化应激增加，导致人体发展多种病症或疾病，诸如，例如，炎性过程、致癌过程或变性过程。
尽管还没有详细知晓这些物质的潜在作用机制，但是，存在充分的关于抗氧化剂的分布、活性和调控的研究，以使得从营养的观点研发作用策略和涉及新抗氧化制剂的化妆品。这些新的项目包括减少由UV光诱发的癌症危险，由光作用引起的衰老，预防和治疗引起皮肤脱皮的疾病以及维持良好的健康和改善衰老作用。
一些植物天然产生SOD，诸如花椰菜、小麦和大麦，但是，当人体消化SOD时，SOD被胃酸和肠道酶快速破坏，因此，其几乎不能到达血流中。此外，人体在大约10岁的年龄具有SOD产生的最大峰。通过消费适量的适当前体分子的补充物，可能升高血液SOD水平。还已知，小麦新芽是这些前体的丰富来源。然而，仍然存在相同的消化过程导致的SOD破坏的问题。
因此，合成模拟SOD酶的化合物对于补偿内源性SOD活性的可能的缺乏或不存在是必要的，并且因此不仅能够治疗具有缺少或缺乏该酶活性的常见病因的多种病理或疾病，而且能够利用它们作为食品或化妆品试剂的能力。理想地，合成的模拟化合物必须具有低毒性，并且还能够以最低的可能的化合物浓度进行歧化反应。使用较低浓度或剂量的SOD模拟物将减少治疗成本以及与副作用和免疫原性的发展相关的危险。
已知在美容产品中使用SOD以减少皮肤中自由基的伤害，例如，减少由于放疗引起的纤维化。主要的专利ES2355784已经提到与该作用相关的文献目录。最近也与美容效果相关的研究是Campana F.,Zervoudis S.等,2004.Topical superoxide dismutase reducespost-irradiation breast cancer fibrosis(局部超氧化物歧化酶减轻辐射后乳腺癌纤维化).J Cell Mol Med.Jan-Mar；8(1):109-16。可能解释SOD作为能够逆转纤维化的试剂的作用的机制是肌成纤维细胞向成纤维细胞的可能的回复。
用作化妆品的SOD模拟物的实例是lipocromano-6(EP2113242)或专利申请US20130287696中所述的那种，专利申请US20130287696公开了通过使用有效量的聚乙二醇化的SOD模拟物，任选地与第二保存添加剂组合，防止食物变质和氧化的方法。该专利的SOD模拟物的具体实例显示如下：
还已知，口服服用SOD，以去除皱纹或重建组织，但是，没有证据表明这些口服产品被机体吸收。
在现有技术中没有找到具体公开主要专利ES2355784中开发的金属络合物的文献。因此，它们作为化妆品或作为食品试剂的应用都没有被公开。
主要专利中所述的金属络合物具有低毒性、低IC50值，并且不引起免疫原性的发展。这些金属络合物的低IC50值具有重要的含义，原因在于该值越低，引起需要的模仿效应所需要的化合物的量越低。因此，使用较低量的络合物实现歧化反应将极大地减少副作用。
此外，由于它们在血浆中的稳定性，前述金属络合物具有长半衰期，并且它们在施用后不表现出组织分布的问题。
发明描述
本发明涉及模拟SOD的金属络合物，作为化妆品或食品试剂的应用，所述金属络合物由具有连接到分子中心结构上的杂环喹啉的中间大环聚氮杂环吡啶烷化合物获得。
术语“食品试剂”在本文件中涉及下述备选物中的任一种：食品添加剂、功能食品、膳食补充物或功能饮料。
在本文件中，金属络合物涉及式1的中间化合物与至少一个金属离子(优选Cu(II)、Fe(II)或Mn(II))的任何分子连接，并且最优选地，其中所述金属离子是Mn(II)。
在本发明中，SOD模拟络合物涉及能够模仿、补充并最终改善内源性SOD酶的活性和/或功能的金属络合物，其作为化妆品、个人卫生用品或食品试剂。
ES2355784中所述的金属络合物可以包括在制剂中用于食品或化妆品应用，并且按照现有技术中的已知技术以多种方式施用，诸如皮内注射或通过胶囊、糖衣丸或片剂口服。
作为用于化妆品的制剂或个人卫生用品，它们可以形成除臭剂、止汗剂、头发和皮肤护理产品的一部分，并且可以是，例如，保湿剂、清洁产品或二者的组合。用于化妆品的制剂或个人卫生产品还可以以粉剂或固体条的形式，或其他固体形式，诸如，例如，乳剂、奶液、洗液、乳液、糊剂、液体、凝胶、气雾剂、固体形式、胶状物、油膏、面膜、分散液、混悬液、香波、泡沫剂、喷雾剂或无水液体。
类似地，用于化妆品应用的固体形式可以在存在需要的赋形剂的条件下制备，所述赋形剂选自包括但不限于下述的组：甘露醇、聚乙烯吡咯烷酮、微晶纤维素、硅胶、滑石、硬脂酸镁、氧化钛、染料和抗氧化剂。
因此，本发明更具体地涉及具有至少一个金属离子的式1的模拟超氧化物歧化酶的金属络合物作为化妆品或食品试剂的应用。
所述金属离子优选选自Cu(II)、Fe(II)和Mn(II)，并且更优选是Mn(II)。
本发明还涉及具有至少一个金属离子的式1的模拟SOD的金属络合物用于制备食品试剂的应用(所述食品试剂可以是食品添加剂、功能食品、膳食补充剂或功能饮料)，或用于制备个人卫生产品或化妆品制剂的应用。所述金属离子优选选自Cu(II)、Fe(II)和Mn(II)，并且更优选是Mn(II)。
另外，本发明还涉及包含至少一种上文定义的具有至少一种金属离子的式1的模拟SOD的金属络合物的化妆品制剂或个人卫生产品。
该化妆品制剂或个人卫生产品可以配制成乳剂、糊剂、奶液、凝胶、洗液、油膏、混悬液、分散液、粉剂、香波、泡沫剂、喷雾剂或固体条。
此外，本发明涉及包含至少上文定义的具有至少一种金属离子的式1的模拟SOD的金属络合物的食品添加剂、膳食补充物、功能食品或功能饮料。
由于它们具有降低的毒性和低IC50值，本发明的金属络合物克服了现有技术中列出的问题。本发明的金属络合物的低IC50具有重要的含义，原因在于，该值越低，引起需要的模仿效应所需要的络合物的量越小。因此，使用较少量的络合物实现歧化反应极大地减少了副作用。
另外，本发明的金属络合物具有高稳定性(如主要专利ES2355784中所示的)和半衰期，避免了施用后在组织中的分布问题以及免疫原性的发展。
本发明的一个优选实施方案涉及模拟化合物的应用，其中结合在式1的化合物上的金属离子选自Cu(II)、Fe(II)和Mn(II)。
附图描述
图1:将8期青鳉鱼(Medaka)胚胎与氧化剂H2O2和化合物Pytren-4Q+Mn温育72小时后获得的结果的图示，详见实施例。
图2:将8期青鳉鱼(Medaka)胚胎与氧化剂H2O2和化合物Pytren-4Q+Mn温育14天后获得的结果的图示，如实施例所述。
实施例
1.材料和方法
1.1青鳉鱼胚胎
将个体成体(品种Cab,Carolina Biological Supply,(North Carolina))放在具有连续的水流的27℃的水箱中，并且有14小时光和10小时黑暗的光周期。每天用卤虫无节幼体(Artemia nauplii)喂鱼两次，卤虫无节幼体每天从商购的囊孢孵化，并且每天用干食物喂一次。
每天收集受精卵，保存在Yamamoto溶液(0.13M NaCl,2.7mM KCl,1.8mM CaCl2和0.24mM NaHCO3,pH 7.3)(Yamamoto T.,Medaka(killifish):Biology and strains.1975,Tokyo:Keigaku Pub.Co)中，并且在培养箱中在26℃保持。按照Iwamatsu的描述(IwamatsuT.,Stages of normal development in the medaka Oryzias latipes.Mech Dev.2004,Vol.121,第605-618页)确定胚胎阶段。
1.2使用青鳉鱼胚胎进行存活分析
将8期青鳉鱼胚胎(早期桑葚胚阶段，Iwamatsu,2004)分成2个60个胚胎的组和一个30个胚胎的组。将一个60个胚胎的组用以250μM的浓度溶解在Yamamoto溶液中的Pytren-4Q+Mn处理4天。将另一个60个胚胎的组在Yamamoto溶液中温育4天。该组用作阴性对照。将30个胚胎的组，即，阳性对照组，用浓度为100μM的维生素C(抗氧化性化合物)的Yamamoto溶液处理4天。温育4天后，将胚胎用Yamamoto溶液清洗。将60个胚胎的组逐一分成两个30个胚胎的组。将所有组的胚胎单独放置在96孔板的孔中，每个孔包含200μl含有不同浓度的H2O2的Yamamoto溶液，浓度取决于观察死亡率的温育时间的延长。当在放置到H2O2Yamamoto溶液中后72小时观察死亡率时，所用的H2O2浓度为22.5mM。将每个60个胚胎的原始组的三十个胚胎和用维生素C处理的组的30个胚胎用浓度为22.5mM的H2O2Yamamoto溶液处理。当在放置到H2O2Yamamoto溶液中后14天观察死亡率时，所用的H2O2浓度为7.5mM。将每个60个胚胎的原始组的三十个胚胎用浓度为7.5mM的H2O2Yamamoto溶液处理。该实验在72小时的检测中共重复6次，在14天的检测中共重复3次。
1.3统计学分析
为了评估存活差异，在比较这3个检测组时，使用单向方差分析统计学检测(ANOVA)确定是否存在统计学显著性差异。然后，使用Tukey′spost-hoc检验确定这3个组中哪一组具有统计学显著性差异。当比较2个检测组时，使用统计学斯氏(Student’s)t检验。在所有情形中，将显著性水平设为p<0.05。所有这些分析使用GraphPad Prism 5.0a程序进行。
2.结果
使用对胚胎无毒的250μM浓度的化合物Pytren-4Q+Mn进行检测，并且在两个不同的测定中测量它们的抗氧化能力。第一个检测测量在用22.5μM H2O2温育72小时后的死亡率(显示在图1中)。第二个检测测量在用22.5μM H2O2温育14天后的死亡率(显示在图2中)。两个检测表明响应由H2O2引起的氧化应激的死亡率的显著下降。在72小时进行的检测表明Pytren-4Q+Mn和维生素C二者都降低死亡率，在对照中为48.44±4.40％，在用Pytren-4Q+Mn处理的胚胎中为24.96±7.11％，并且在用维生素C处理的胚胎中为25.99±5.25％(表1)。因此，本发明的化合物Pytren-4Q+Mn在所检测的浓度发挥与维生素C相似的抗氧化活性。
表1.在温育72小时的本发明的实施例检测中获得的数据。
| 72小时 | 对照 | Pytren-4Q+Mn | 维生素C |
| 重复1 | 62.5 | 50 | 40.63 |
| 重复2 | 56.25 | 43.75 | 43.75 |
| 重复3 | 50 | 12.9 | 15.63 |
| 重复4 | 43.75 | 15.63 | 14.3 |
| 重复5 | 46.9 | 18.75 | 20.8 |
| 重复6 | 31.25 | 8.7 | 20.8 |
| 平均值 | 48.44 | 24.96 | 25.99 |
| 标准偏差 | 10.78 | 17.41 | 12.87 |
| 标准误差 | 4.40 | 7.11 | 5.25 |
在14天进行的检测表明Pytren-4Q+Mn降低死亡率，在对照中为51.27±3.12％，在用Pytren-4Q+Mn处理的胚胎中为41.47±1.52％(表2)。主要的差异归因于这样的事实：在14天的检测尽管更久，但是其更灵敏，原因在于可以在以后检测到小的致死性作用。
表2.在温育14天的本发明的实施例检测中获得的数据。
| 14天 | 对照 | Pytren-4Q+Mn |
| 重复1 | 46.9 | 39.3 |
| 重复2 | 57.3 | 40.7 |
| 重复3 | 49.6 | 44.4 |
| 平均值 | 51.27 | 41.47 |
| 标准偏差 | 5.40 | 2.64 |
| 标准误差 | 3.12 | 1.52 |
获得的数据表明化合物Pytren-4Q+Mn在250μM的浓度具有与100μM的维生素C相似的抗氧化特性。
Claims (9)
1.具有至少一个金属离子的式1的模拟超氧化物歧化酶的金属络合物作为化妆品的应用：
2.具有至少一个金属离子的式1的模拟超氧化物歧化酶的金属络合物作为食品试剂的应用。
3.根据权利要求1或2中任一项所述的应用，其中所述金属离子选自Cu(II)、Fe(II)和Mn(II)。
4.根据权利要求3所述的应用，其中所述离子是Mn(II)。
5.权利要求1-4中任一项所述的具有至少一个金属离子的式1的模拟超氧化物歧化酶的金属络合物在制备食品添加剂、膳食补充剂、功能食品或功能饮料中的应用。
6.权利要求1-4中任一项所述的具有至少一个金属离子的式1的模拟超氧化物歧化酶的金属络合物在制备化妆品制剂或个人卫生产品中的应用。
7.一种化妆品制剂或个人卫生产品，其包含至少一种权利要求1-4中任一项所述的具有至少一个金属离子的式1的模拟超氧化物歧化酶的金属络合物。
8.根据权利要求7所述的化妆品制剂或个人卫生产品，其中所述制剂或产品配制成乳剂、糊剂、奶液、凝胶、洗液、油膏、混悬液、分散液、粉剂、香波、泡沫剂、喷雾剂或固体条。
9.一种膳食补充物、功能食品或功能饮料，其包含至少一种权利要求1-4中任一项所述的具有至少一个金属离子的式1的模拟超氧化物歧化酶的金属络合物。
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| CN110869054A (zh) * | 2017-07-04 | 2020-03-06 | 比诺斯生物科技有限公司 | 大环氮杂吡啶环蕃金属复合物在治疗疾病中的用途 |
| CN110869054B (zh) * | 2017-07-04 | 2022-06-07 | 比诺斯生物科技有限公司 | 大环氮杂吡啶环蕃金属复合物在治疗疾病中的用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2543850A2 (es) | 2015-08-24 |
| US9750677B2 (en) | 2017-09-05 |
| US20170007521A1 (en) | 2017-01-12 |
| ES2543850R2 (es) | 2015-09-07 |
| EP3112367A4 (en) | 2017-05-03 |
| WO2015124824A1 (es) | 2015-08-27 |
| JP2017507179A (ja) | 2017-03-16 |
| EP3112367A1 (en) | 2017-01-04 |
| ES2543850B1 (es) | 2016-06-16 |
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