卟啉衍生物的合成及抗肿瘤活性研究
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摘要
卟啉类化合物具有较好的光学性能,目前作为光敏剂被广泛用于多种肿瘤的诊断和光动力治疗。同时在其他领域也有广泛应用,已成为人们研究的热点。对于光敏剂的研究主要集中在四苯基卟啉类化合物及其金属络合物,由于激发波长短,对动物组织穿透能力差,不能用于深层肿瘤的治疗。为延长卟啉化合物的激发波长,增强其组织穿透能力,我们首先设计合成了一系列萘基卟啉、亚甲二氧基苯基卟啉化合物,对这些化合物的光学特性研究表明,与四苯基卟啉相比,由于亚甲二氧基和萘基的引入,紫外吸收波长以及荧光激发波长都有不同程度的红移,有增强对动物组织的穿透力的可能。在此基础上进一步合成了一系列具有抗肿瘤活性的小分子酸类化合物与卟啉缩合成的酯类化合物,并对其进行了抗肿瘤活性研究。
通过比较,单羟基取代萘基卟啉以及单羟基取代苯基亚甲二氧基卟啉化合物的合成采用了Adler法,产率约6%,虽然产率不太高,但制备工艺简单,产品易得,且后处理方便。
小分子酸类化合物与单羟基取代萘基卟啉的连接的采用DCC(二环己基碳二亚胺)脱水法,产率约15%～23%。
最后,采用MTT(噻唑蓝)法对化合物21～28对小鼠肺腺癌细胞LA795的体外抗肿瘤活性进行了研究。结果表明,化合物23、28有显著的体外抗肿瘤活性,同时具有剂量-效应关系,当药物浓度达到800μmol·L-1时,肿瘤抑制率可达到80%;化合物5、6、21、26虽然在实验浓度下没有显著的抑制肿瘤细胞生长的效果,但也可以初步看出具有剂量依赖性,随着药物浓度的增加对肿瘤细胞生长的抑制率也在逐渐增大;化合物24和27在低浓度时对肿瘤细胞生长的抑制率较低,但当浓度增加到一定程度时抑制率增加较为显著。
With good optical properties, porphyrins have been widely used as photosensitizer for clinical diagnose and photodynamic therapy of many kinds of cancer, while they have also been widely used in many other fields. Porphyrins have become the hot spot of science research. The study of photosensitizer was mainly on tetraphenyl porphyrins and its metal complex. Because exitation wavelength is short, penetrating power for animal tissue is not so good, the current photosensitizers are not fit for cancer in deep tissue.
In this paper, a series of naphthylporphyrins and methylenedioxy phenylporphyrins were synthesized first for extanding exitation wavelength and reforcing penetrating power for animal tissue, The results on optical property studies of these compounds show that the introduction of naphthyl and methylenedioxy group can enhance the conjugate degree of the porphyrin to a certain extent. Further a group of ester compounds of porphyrins and small molecule acids with anti-tumor activities were synthesized.
The Adler`s method was employed to synthesize naphthylporphyrins and methylenedioxy phenylporphyrins. The yields were not so high, but the prossese products were easily obtained. The ester compounds was synthesized by DCC dehydration, yields 15%～23%.
Finally, MTT method in vitro was used to observe anti-tumor activities of compounds 21～28 on mouse pulmonary adenocarcinoma cells. The result show that compounds 23 and 28 have evident activity and the dosage-effect relation. The inhibition rate upto 80% at concentration 800μmol·L~(-1). Compounds 5, 6, 21, 26 have no evident activity, but they are dose dependent. Compounds 24 and 27 have a little activity under the experiment concentration, but they are more active when concentration was upto a certain degree.
通过比较,单羟基取代萘基卟啉以及单羟基取代苯基亚甲二氧基卟啉化合物的合成采用了Adler法,产率约6%,虽然产率不太高,但制备工艺简单,产品易得,且后处理方便。
小分子酸类化合物与单羟基取代萘基卟啉的连接的采用DCC(二环己基碳二亚胺)脱水法,产率约15%～23%。
最后,采用MTT(噻唑蓝)法对化合物21～28对小鼠肺腺癌细胞LA795的体外抗肿瘤活性进行了研究。结果表明,化合物23、28有显著的体外抗肿瘤活性,同时具有剂量-效应关系,当药物浓度达到800μmol·L-1时,肿瘤抑制率可达到80%;化合物5、6、21、26虽然在实验浓度下没有显著的抑制肿瘤细胞生长的效果,但也可以初步看出具有剂量依赖性,随着药物浓度的增加对肿瘤细胞生长的抑制率也在逐渐增大;化合物24和27在低浓度时对肿瘤细胞生长的抑制率较低,但当浓度增加到一定程度时抑制率增加较为显著。
With good optical properties, porphyrins have been widely used as photosensitizer for clinical diagnose and photodynamic therapy of many kinds of cancer, while they have also been widely used in many other fields. Porphyrins have become the hot spot of science research. The study of photosensitizer was mainly on tetraphenyl porphyrins and its metal complex. Because exitation wavelength is short, penetrating power for animal tissue is not so good, the current photosensitizers are not fit for cancer in deep tissue.
In this paper, a series of naphthylporphyrins and methylenedioxy phenylporphyrins were synthesized first for extanding exitation wavelength and reforcing penetrating power for animal tissue, The results on optical property studies of these compounds show that the introduction of naphthyl and methylenedioxy group can enhance the conjugate degree of the porphyrin to a certain extent. Further a group of ester compounds of porphyrins and small molecule acids with anti-tumor activities were synthesized.
The Adler`s method was employed to synthesize naphthylporphyrins and methylenedioxy phenylporphyrins. The yields were not so high, but the prossese products were easily obtained. The ester compounds was synthesized by DCC dehydration, yields 15%～23%.
Finally, MTT method in vitro was used to observe anti-tumor activities of compounds 21～28 on mouse pulmonary adenocarcinoma cells. The result show that compounds 23 and 28 have evident activity and the dosage-effect relation. The inhibition rate upto 80% at concentration 800μmol·L~(-1). Compounds 5, 6, 21, 26 have no evident activity, but they are dose dependent. Compounds 24 and 27 have a little activity under the experiment concentration, but they are more active when concentration was upto a certain degree.
引文
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