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用于乳腺癌硼中子俘获治疗的硼载体五甘氨硼烷醇的合成及细胞毒性

Synthesis and cytotoxicity of the boron carrier pentagamaboronon-0-ol for boron neutron capture therapy against breast cancer.

作者信息

Utomo Rohmad Yudi, Wulandari Febri, Novitasari Dhania, Susidarti Ratna Asmah, Kirihata Mitsunori, Hermawan Adam, Meiyanto Edy

机构信息

Cancer Chemoprevention Research Center, Faculty of Pharmacy, Universitas Gadjah Mada Sekip Utara II, Yogyakarta, Indonesia.

Department of Pharmaceutical Chemistry, Laboratory of Medicinal Chemistry, Faculty of Pharmacy, Universitas Gadjah Mada Sekip Utara II, Yogyakarta, Indonesia.

出版信息

J Adv Pharm Technol Res. 2022 Jan-Mar;13(1):70-76. doi: 10.4103/japtr.japtr_220_21. Epub 2022 Jan 21.

DOI:10.4103/japtr.japtr_220_21
PMID:35223445
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8820341/
Abstract

Boronic acid-containing curcumin analog, pentagamaboronon-0 (PGB-0), acts as a potential boron-carrier agent but has limited water solubility. Thus, a new compound (PGB-0-ol) with better chemical and pharmacological properties than PGB-0 has been synthesized. Molecular docking was performed using a molecular operating environment. Prediction of PGB-0-ol absorption, distribution, metabolism, and excretion (ADME) was performed using pkCSM software. PGB-0-ol was synthesized by adding NaBH to PGB-0 and stirring for 1 h. The crude PGB-0-ol was purified using preparative layer chromatography. Cell viability was evaluated using the trypan blue exclusion assay. In comparison to PGB-0 based on molecular docking study, PGB-0-ol could interact in with several cancer biomarkers, such as human epidermal growth factor2 epidermal growth factor receptor, IκB kinase, folate receptor-α, and integrin αβ. PGB-0-ol also showed an improved ADME profile because of its higher water solubility than PGB-0. PGB-0-ol was synthesized by selective ketone reduction of PGB-0 into primary alcohol by sodium borohydrate producing 30% yield. The cytotoxicity of PGB-0-ol against several breast cancer cells was lower than that of PGB-0. The novel compound PGB-0-ol was synthesized using simple steps. PGB-0-ol has low cytotoxicity against breast cancer cells and could be applied in boron neutron capture therapy as a boron carrier.

摘要

含硼酸的姜黄素类似物五戊硼酸-0（PGB-0）作为一种潜在的硼载体剂，但水溶性有限。因此，已合成了一种化学和药理性质比PGB-0更好的新化合物（PGB-0-醇）。使用分子操作环境进行分子对接。使用pkCSM软件预测PGB-0-醇的吸收、分布、代谢和排泄（ADME）。通过向PGB-0中加入硼氢化钠并搅拌1小时来合成PGB-0-醇。使用制备层色谱法纯化粗制的PGB-0-醇。使用台盼蓝排斥试验评估细胞活力。基于分子对接研究，与PGB-0相比，PGB-0-醇可以与几种癌症生物标志物相互作用，如人表皮生长因子2表皮生长因子受体、IκB激酶、叶酸受体-α和整合素αβ。由于PGB-0-醇的水溶性高于PGB-0，其ADME特性也有所改善。通过硼氢化钠将PGB-0选择性酮还原为伯醇来合成PGB-0-醇，产率为30%。PGB-0-醇对几种乳腺癌细胞的细胞毒性低于PGB-。新型化合物PGB-0-醇的合成步骤简单。PGB-0-醇对乳腺癌细胞的细胞毒性较低，可作为硼载体应用于硼中子俘获治疗。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/90da/8820341/43b98d1952d9/JAPTR-13-70-g007.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/90da/8820341/224e99731010/JAPTR-13-70-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/90da/8820341/85ab7c05ad07/JAPTR-13-70-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/90da/8820341/43b98d1952d9/JAPTR-13-70-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/90da/8820341/a7e00525f69e/JAPTR-13-70-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/90da/8820341/68c05a0117b5/JAPTR-13-70-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/90da/8820341/471d0b48f103/JAPTR-13-70-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/90da/8820341/33ddeaff693f/JAPTR-13-70-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/90da/8820341/224e99731010/JAPTR-13-70-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/90da/8820341/85ab7c05ad07/JAPTR-13-70-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/90da/8820341/43b98d1952d9/JAPTR-13-70-g007.jpg

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