WO2010081266A1 - 延胡索乙素的新用途 - Google Patents
延胡索乙素的新用途 Download PDFInfo
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- WO2010081266A1 WO2010081266A1 PCT/CN2009/000563 CN2009000563W WO2010081266A1 WO 2010081266 A1 WO2010081266 A1 WO 2010081266A1 CN 2009000563 W CN2009000563 W CN 2009000563W WO 2010081266 A1 WO2010081266 A1 WO 2010081266A1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Definitions
- This invention relates to new uses of tetrahydropalmatine.
- Corydalis is the dry tubers of the poppy plant, the genus Corydalis, which has the effect of promoting blood circulation, benefiting gas and relieving pain. Its main chemical component is alkaloid, of which tetrahydropalmatine (structural formula is shown in formula I) is a tertiary amine alkaloid with the strongest analgesic effect, analgesic, sedative, sleep aid and stability, especially for the gastrointestinal system. The resulting dull pain is effective.
- tetrahydropalmatine has been used as an analgesic and sleepless non-prescription drug, such as tetrahydropalmatine sulfate tablets and Qiangtongning. However, none of them reported on anti-tumor.
- Lung cancer is a common malignant tumor of the lung, and its mortality rate has been the highest in cancer mortality.
- Most lung cancers originate from the bronchial mucosa.
- Chemotherapy can be used alone in advanced lung cancer cases to relieve symptoms or to be combined with surgery and radiotherapy to prevent cancer metastasis, recurrence, and cure.
- chemotherapeutic drugs are cyclophosphamide, 5-fluorouracil, mitomycin (:, doxorubicin, procarbazine, vincristine, methotrexate, nitrosourea, cisplatin, etc.).
- mitomycin :, doxorubicin, procarbazine, vincristine, methotrexate, nitrosourea, cisplatin, etc.
- tetrahydropalmatine provided by the present invention is: the tetrahydropalmatine or the drug thereof of the formula I
- the tetrahydropalmatine may be a left-handed body, a right-handed body or a racemate, and is preferably a drusen of the formula II;
- the present invention also protects a drug which inhibits proliferation of eukaryotic tumor cells, and its active ingredient is tetrahydropalmatine of the formula I or a pharmaceutically acceptable salt thereof.
- the eukaryotic organism described in the present invention is a mammal.
- the tumor cells are cancer cells; the cancer cells may specifically be breast cancer cells, liver cancer cells, pancreatic cancer cells, lung cancer cells, brain cancer cells, ovarian cancer cells, uterine cancer cells, testicular cancer cells, skin cancer cells, gastric cancer A cell, a nasopharyngeal cancer cell, a colon cancer cell, a bladder cancer cell, an anal cancer cell, or a rectal cancer cell; preferably a lung cancer cell.
- novel use of the tetrahydropalmatine provided by the present invention is also: The use of tetrahydropalmatine or a pharmaceutically acceptable salt thereof represented by the formula (I) for the preparation of a medicament for preventing and/or treating a tumor.
- the tetrahydropalmatine may be a left-handed body, a right-handed body or a racemate, and is preferably a left-handed tamarindine represented by the formula.
- the tumor cells are cancer cells; the cancer cells may specifically be breast cancer cells, liver cancer cells, pancreatic cancer cells, lung cancer cells, brain cancer cells, ovarian cancer cells, uterine cancer cells, testicular cancer cells, skin cancer cells, gastric cancer A cell, a nasopharyngeal cancer cell, a colon cancer cell, a bladder cancer cell, an anal cancer cell, or a rectal cancer cell; preferably a lung cancer cell.
- a tetrahydropalmatine or a pharmaceutically acceptable salt thereof represented by Formula I is also within the scope of the present invention to use a tetrahydropalmatine or a pharmaceutically acceptable salt thereof represented by Formula I as an active ingredient for the prevention and/or treatment of a tumor.
- the preventive and/or therapeutic tumor drug can be introduced into the body such as muscle, intradermal, subcutaneous, intravenous, mucosal tissue by injection, jetting, nasal drops, eye drops, infiltration, absorption, physical or chemical mediated methods; Other substances are mixed or wrapped and introduced into the body.
- An antitumor drug containing tetrahydropalmatine or a pharmaceutically acceptable salt thereof as an active ingredient, and if necessary, one or more pharmaceutically acceptable carriers may be added to the above drug.
- the carrier includes conventional diluents, excipients, fillers, binders, wetting agents, disintegrating agents, absorption enhancers, surfactants, adsorption carriers, lubricants and the like in the pharmaceutical field.
- the preventive and/or therapeutic tumor drug prepared by using tetrahydropalmatine or a pharmaceutically acceptable salt thereof can be prepared into various forms such as an injection, a tablet, a powder, a granule, a capsule, an oral solution, an ointment, a cream, and the like.
- the above various dosage forms of the drug can be prepared according to a conventional method in the pharmaceutical field.
- Fig. 1 is a schematic diagram showing the tumor size in nude mice of each group on the 28th day after administration, wherein the blank in the positive control group represents tumor disappearance.
- Tumor cell line human lung cancer cell line A549 (Shanghai Institute of Cell Biology, Chinese Academy of Sciences);
- Test animals Male BALB/c nude mice (SPF grade, Institute of Experimental Animals, Chinese Academy of Medical Sciences), aged 4-6 weeks, 24 animals;
- the animal's body weight range at the start of administration 16-18 g, and the animal's initial body weight is not more than or less than 20% of the average body weight;
- Negative control 0.9% sodium chloride injection (physiological saline).
- the human lung cancer cell line A549 was suspended and cultured in RPMI 1640 medium (containing penicillin 100 U/mL, streptomycin 100 U /mL) containing 10% calf serum, and placed in a cell culture at 37 ° C, 5% CO 2 . Cultivate in the box.
- the logarithmic growth phase A549 cells were collected and centrifuged, and counted after staining with a mass percentage of 0.4% trypan blue solution.
- tumor-bearing murine prepared.
- the tumor was grown to about lg, and the mice were inoculated to prepare F1 generation tumor-bearing mice.
- Tumor-bearing animals with strong tumor growth and no ulceration and good health were taken, and tumors were taken under aseptic conditions to prepare 3nmi 3 , which was inoculated into the right axilla of each animal.
- the tumor growth was observed after inoculation in nude mice.
- the tumor volume was 100-300 mm 3 , the tumor size and body weight were screened.
- the tumor volume was too large and no tumorigenicity was selected.
- Tumor-bearing mice were randomly divided into: negative control group, positive control group and tetrahydropalmatine group, each group
- Negative control group normal saline was administered
- Tetrahydropalmatine group L-Tallowhosin (Chengdu Cisco Hua Biotechnology Co., Ltd.), the intragastric dose is lOOmg I kg body weight;
- Positive control group 0.5 mg I ml of cisplatin solution was administered, and the intraperitoneal dose was: 0.1 ml/lOg body weight.
- the long diameter, short diameter and body weight of the tumor were measured and recorded by vernier calipers twice a week from the time of grouping and administration, including the first dose and the last dose, the tumor volume was calculated and the tumor growth between the groups was compared.
- the difference in the curves, the tumor size in the nude mice of each group on the 28th day after administration is shown in Fig. 1.
- V l/2x long diameter X short diameter 2 ⁇ evaluation of curative effect based on tumor volume
- Vt daily measurement of tumor volume obtained by tumor
- T/C% RTV average of the administration group / RTV average of the control group ⁇ 100%
- tetrahydropalmatine can effectively inhibit tumor growth, and the tumor volume is significantly smaller than the negative control. It can be seen that tetrahydropalmatine, which has been widely used for analgesic action, has excellent antitumor activity, and the results indicate that tetrahydropalmatine can be used for the preparation of a medicament for treating lung cancer.
- the invention broadens the field of medical application of tetrahydropalmatine.
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Abstract
本发明公开了一种延胡索乙素的新用途。该新用途是式I所示的延胡索乙素或其药学上可接受的盐在制备抑制真核生物肿瘤细胞增殖药物中的应用和在制备预防和/或***药物中的应用。裸鼠体内实验结果表明, 延胡索乙素可以有效抑制肿瘤的生长, 肿瘤体积明显小于阴性对照。由此可以看出,目前已经广泛用于镇痛作用的延胡索乙素,具有很好的抗肿瘤活性,该结果表明了延胡索乙素可以用于制备治疗癌症的药物,尤其是治疗肺癌的药物。本发明拓宽了延胡索乙素的医 药应用领域。
Description
延胡索乙素的新用途 技术领域
本发明涉及延胡索乙素的新用途。
背景技术
延胡索为罂粟科紫堇植物延胡索的干燥块茎, 具有活血、 利气、 止痛 的功效。 其主要化学成分为生物碱, 其中延胡索乙素 (结构式如式 I所 示) 属叔胺类生物碱, 镇痛作用最强, 具有镇痛、 镇静、 助眠及安定作 用, 尤其对胃肠***引起的钝痛有效。 目前延胡索乙素已作为镇痛助眠类 非处方药药品, 例如硫酸延胡索乙素片、 强痛宁等。 但均未见其在抗肿瘤 方面的报道。
肺癌是一种常见的肺部恶性肿瘤, 其死亡率已占癌症死亡率之首。 绝 大多数肺癌起源于支气管粘膜上皮, 近年来, 随着吸烟和各种环境因素的 影响, 世界各国特别是工业发达国家, 肺癌的发病率和病死率均迅速上 升。 化疗可以单独用于晚期肺癌病例, 以缓解症状或与手术、 放疗综合应 用, 以防止癌转移、 复发、 提高治愈率。 常用化疗药物有环磷酰胺、 5-氟 脲嘧啶、 丝裂霉素 (:、 阿霉素、 甲基苄肼、 长春新碱、 氨甲嘌呤、 环已亚 硝脲、 顺氯氨铂等。 但是目前临床上尚缺少一种安全有效治疗肺癌的药 物。
发明公开
本发明的目的是提供延胡索乙素的新用途。
本发明所提供的延胡索乙素的用途为: 式 I所示的延胡索乙素或其药
学上可接受的盐在制备抑制真核生物肿瘤细胞增殖药物中的应用
所述延胡索乙素可为左旋体、 右旋体或消旋体, 优选为式 II所示的左 旋延胡索乙素;
本发明还保护一种抑制真核生物肿瘤细胞增殖的药物, 它的有效成分 为式 I所示的延胡索乙素或其药学上可接受的盐。
本发明中所述真核生物为哺乳动物。
所述肿瘤细胞为癌细胞; 所述癌细胞具体可为乳腺癌细胞、 肝癌细 胞、 胰腺癌细胞、 肺癌细胞、 脑癌细胞、 卵巢癌细胞、 子宫癌细胞、 睾丸 癌细胞、 皮肤癌细胞、 胃癌细胞、 鼻咽癌细胞、 结肠癌细胞、 膀胱癌细 胞、 ***癌细胞或直肠癌细胞; 优选为肺癌细胞。
本发明提供的延胡索乙素的新用途还为: 式 ( I ) 所示的延胡索乙素 或其药物学上可接受的盐在制备预防和 /或***药物中的应用。
所述延胡索乙素可为左旋体、 右旋体或消旋体, 优选为式 Π所示的左 旋延胡索乙素。
所述肿瘤细胞为癌细胞; 所述癌细胞具体可为乳腺癌细胞、 肝癌细 胞、 胰腺癌细胞、 肺癌细胞、 脑癌细胞、 卵巢癌细胞、 子宫癌细胞、 睾丸 癌细胞、 皮肤癌细胞、 胃癌细胞、 鼻咽癌细胞、 结肠癌细胞、 膀胱癌细 胞、 ***癌细胞或直肠癌细胞; 优选为肺癌细胞。
以式 I所示的延胡索乙素或其药学上可接受的盐为有效成分制备的预 防和 /或***的药物, 也属于本发明的保护范围。
所述预防和 /或***药物可通过注射、 喷射、 滴鼻、 滴眼、 渗透、 吸收、 物理或化学介导的方法导入机体如肌肉、 皮内、 皮下、 静脉、 粘膜 组织; 或是被其他物质混合或包裹后导入机体。
以延胡索乙素或其药学上可接受的盐为活性成分的抗肿瘤药物, 需要 的时候, 在上述药物中还可以加入一种或多种药学上可接受的载体。 所述 载体包括药学领域常规的稀释剂、 赋形剂、 填充剂、 粘合剂、 湿润剂、 崩 解剂、 吸收促进剂、 表面活性剂、 吸附载体、 润滑剂等。
用延胡索乙素或其药学上可接受的盐制备的预防和 /或***药物可 以制成注射液、 片剂、 粉剂、 颗粒剂、 胶囊、 口服液、 膏剂、 霜剂等多种形 式。 上述各种剂型的药物均可以按照药学领域的常规方法制备。
以下的实施例便于更好地理解本发明, 但并不限定本发明。
附图说明
图 1为给药后第 28天各组裸鼠体内肿瘤大小示意图, 其中阳性对照组 中空白处代表肿瘤消失。
实施发明的最佳方式
下述实施例中的实验方法, 如无特别说明, 均为常规方法
实施例 1、 延胡索乙素对人肺癌细胞增殖能力的影响
肿瘤细胞株: 人肺癌细胞株 A549 (中国科学院上海细胞生物学研究 所) ;
试验动物: 周龄为 4-6周的雄性 BALB/c裸小鼠 (SPF级, 中国医学科 学院实验动物研究所) , 24只;
给药开始时动物体重范围: 16- 18g, 动物的初始体重不超过或低于平 均体重的 20%;
阳性对照品: 顺铂注射液 (ra 科鼎医疗有限公司, 批号:
M071881) ;
阴性对照品: 0.9%氯化钠注射液 (生理盐水) 。
具体操作步骤如下:
(1) 肿瘤细胞的培养
将人肺癌细胞株 A549悬浮培养于含 10%小牛血清的 RPMI 1640培养 基 (含青霉素 100 U/mL、 链霉素 100 U /mL) , 置于 37°C、 5%C02的细胞 孵箱中培养。
每 3天传代一次。 在传代培养 24小时后细胞进入对数生长期即可进行 下一步试验。
(2) 裸鼠移植瘤模型的建立
将对数生长期 A549 细胞收集离心, 用质量百分含量为 0.4%台盼兰溶 液染色后计数。
用上述 RPMI 1640 培养基调整细胞浓度为 ΙχΙΟ7个 / ml, 以 0.2ml / 只接种于裸鼠右侧腋窝皮下, 制备荷瘤种鼠。
待肿瘤生长至 lg左右, 接种小鼠, 制备 F1代荷瘤种鼠。
选择肿瘤生长旺盛且无溃破, 健康情况良好的荷瘤动物, 无菌条件下 取瘤, 制备成 3nmi3, 接种于各动物右侧腋窝皮下。
裸鼠接种后观察肿瘤生长情况, 待肿瘤体积为 100-300mm3时, 按瘤体 积大小及体重进行筛选, 瘤体积过大及未成瘤者不予入选。
将荷瘤鼠随机分组: 阴性对照组、 阳性对照组和延胡索乙素组, 每组
8只, 然后分组给予不同药物。
(3) 供试品的配制
阴性对照组: 给予生理盐水;
延胡索乙素组: 左旋延胡索乙素 (成都思科华生物技术有限公司) , 灌胃剂量为 lOOmg I kg体重;
阳性对照组: 给予 0.5mg I ml 的顺铂溶液, 腹腔给药剂量为: 0. lml/lOg体重。
(4) 给药方法
给药途径及频率: 延胡索乙素和阴性对照品灌胃给药, 每天 1 次, 阳 性对照品腹腔给药, 1次 /周。 给药期限: 4周
(5)实验结果:
在试验过程中, 从分组、 给药开始, 每周 2 次用游标卡尺测量并记录 肿瘤长径、 短径以及体重, 包括首次给药和末次给药当天, 计算肿瘤体积 并比较各组间肿瘤生长曲线的差异, 给药后第 28天各组裸鼠体内肿瘤大小 见图 1。
按照以下公式计算肿瘤体积:
V=l/2x长径 X短径 2 ― 根据肿瘤体积进行疗效评价
按照以下公式计算相对肿瘤体积 (RTV) 和相对肿瘤增殖率 T/C %: RTV=Vt/V0
Vt : 每天测量肿瘤得到的瘤体积
Vo: 初始瘤体积 (给药前)
T/C% = 给药组的 RTV平均值 /对照组的 RTV平均值 χ 100%
利用生物统计学中的 Τ 检验方法, 将各组裸鼠实验结果进行统计整 理, 结果见表 1。
' 表 1 延胡索乙素对人肺癌相对肿瘤体积 (RTV)
及各组内显著性差异 (Ρ ) 结果
其中, "Ρ "值为与阴性对照组相比的显著性差异。 表 2 延胡索乙素对人肺癌相对肿瘤增殖率 (T/C %) 时间 /天 3 7 10 14 18 22 25 28 阴性对 72.6543 49.3087 26.5509 24.3323 20.1204 18.2441 16.0161 16.6303 照组
延胡索 87.6830 73.4258 31.8297 21.2873 14.781 1 21.5647 17.3453 21.9651 乙素组 上述结果表明, 延胡索乙素对人肺癌在体内具有很好的抑制效果。 裸 鼠体内实验结果表明, 延胡索乙素可以有效抑制肿瘤的生长, 肿瘤体积明 显小于阴性对照。 由此可以看出, 目前已经广泛用于镇痛作用的延胡索乙 素, 具有很好的抗肿瘤活性, 该结果表明了延胡索乙素可以用于制备治疗 肺癌的药物。 本发明拓宽了延胡索乙素的医药应用领域。
工业应用
利用裸鼠的人肺癌移植瘤模型对延胡索乙素进行体内抗癌作用研究表 明, 延胡索乙素可以有效抑制肿瘤的生长。 而且由于延胡索乙素为已上市药 物, 其毒性较低, 所以该发现不仅拓宽了延胡索乙素的药用范围, 而且非常 有希望开发成为一种新型高效、 低毒的抗肿瘤药物, 尤其是抗肺癌的药物。
Claims
1、 式 I 所示的延胡索乙素或其药学上可接受的盐在制备抑制真核生 物肿瘤细胞增殖药物中的应用;
(式 I ) 。
2、 根据权利要求 1所述的应用, 其特征在于: 所述延胡索乙素为式 II 所示的左旋延胡索乙素;
(式 II ) 。
3、 根据权利要求 1或 2所述的应用, 其特征在于: 所述真核生物为哺 乳动物; 所述肿瘤细胞为癌细胞; 所述癌细胞为乳腺癌细胞、 肝癌细胞、 胰腺癌细胞、 肺癌细胞、 脑癌细胞、 卵巢癌细胞、 子宫癌细胞、 睾丸癌细 胞、 皮肤癌细胞、 胃癌细胞、 鼻咽癌细胞、 结肠癌细胞、 膀胱癌细胞、 肛 门癌细胞或直肠癌细胞
4、 根据权利要求 3 所述的应用, 其特征在于: 所述癌细胞为肺癌细 胞。
5、 一种抑制真核生物肿瘤细胞增殖的药物, 它的有效成分为式 I所示 的延胡索乙素或其药学上可接受的盐。
6、 根据权利要求 5所述的药物, 其特征在于: 所述真核生物为哺乳动 物; 所述肿瘤细胞为癌细胞; 所述癌细胞为乳腺癌细胞、 肝癌细胞、 胰腺 癌细胞、 肺癌细胞、 脑癌细胞、 卵巢癌细胞、 子宫癌细胞、 睾丸癌细胞、 皮肤癌细胞、 胃癌细胞、 鼻咽癌细胞、 结肠癌细胞、 膀胱癌细胞、 ***癌 细胞或直肠癌细胞.
7、 根据权利要求 6 所述的药物, 其特征在于: 所述癌细胞为肺癌细 胞。
8、 式 I所示的延胡索乙素或其药物学上可接受的盐在制备预防和 /或 ***药物中的应用。
9、 根据权利要求 8所述的应用, 其特征在于: 所述延胡索乙素为式 II 所示的左旋延胡索乙素。
10、 根据权利要求 8或 9所述的应用, 其特征在于: 所述肿瘤为癌。
11、 根据权利要求 10所述的应用, 其特征在于: 所述癌为乳腺癌、 肝 癌、 胰腺癌、 肺癌、 脑癌、 卵巢癌、 子宫癌、 睾丸癌、 皮肤癌、 胃癌、 鼻 咽癌、 结肠癌、 膀胱癌、 ***癌或直肠癌。
12、 根据权利要求 11所述的应用, 其特征在于: 所述癌为肺癌。
13、 一种预防和 /或***的药物, 它的有效成分为式 I所示的延胡 索乙素或其药学上可接受的盐。
14、 根据权利要求 13所述的药物, 其特征在于: 所述肿瘤为癌; 所述 癌为乳腺癌、 肝癌、 胰腺癌、 肺癌、 脑癌、 卵巢癌、 子宫癌、 睾丸癌、 皮 肤癌、 胃癌、 鼻咽癌、 结肠癌、 膀胱癌、 ***癌或直肠癌。
- 15、 根据权利要求 14所述的药物, 其特征在于: 所述癌为肺癌。
16、 根据权利要求 13-15 中任一所述的药物, 其特征在于: 所述药物 的剂型包括注射剂、 片剂、 粉剂、 颗粒剂、 胶囊、 口服液、 膏剂和霜剂。
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CN104490877B (zh) * | 2014-12-10 | 2017-04-12 | 中国科学院化学研究所 | 左旋延胡索乙素衍生物的新用途 |
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