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来自印度尼西亚海洋海绵的含氧多溴二苯醚：X 射线、SAR 和计算研究。

Oxy-Polybrominated Diphenyl Ethers from the Indonesian Marine Sponge, : X-ray, SAR, and Computational Studies.

机构信息

Department of Chemistry, Faculty of Mathematics and Natural Sciences, IPB University, Bogor 16680, Indonesia.

Department of Chemistry, Biology, and Marine Science, University of the Ryukyus, Nishihara 903-0213, Okinawa, Japan.

出版信息

Molecules. 2021 Oct 20;26(21):6328. doi: 10.3390/molecules26216328.

DOI:10.3390/molecules26216328
PMID:34770740
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8588277/
Abstract

Polybrominated diphenyl ether (PBDE) compounds, derived from marine organisms, originate from symbiosis between marine sponges and cyanobacteria or bacteria. PBDEs have broad biological spectra; therefore, we analyzed structure and activity relationships of PBDEs to determine their potential as anticancer or antibacterial lead structures, through reactions and computational studies. Six known PBDEs (-) were isolated from the sponge, ; C NMR data for compound are reported for the first time and their assignments are confirmed by their theoretical C NMR chemical shifts (RMSE < 4.0 ppm). Methylation and acetylation of (2, 3, 4, 5-tetrabromo-6-(3', 5'-dibromo-2'-hydroxyphenoxy) phenol) at the phenol functional group gave seven molecules (-), of which , , and were new. New crystal structures for and are also reported. Debromination carried out on produced nine compounds (, , , -, , and ) of which was new. Debromination product showed a significant IC 8.65 ± 1.11; 8.11 ± 1.43 µM against human embryonic kidney (HEK293T) cells. Compounds and exhibited antibacterial activity against Gram-positive and Gram-negative with MID 0.078 µg/disk. The number of four bromine atoms and two phenol functional groups are important for antibacterial activity ( and ) and cytotoxicity (HEK293T). The result was supported by analysis of frontier molecular orbitals (FMOs). We also propose possible products of acetylation and debromination using analysis of FMOs and electrostatic charges and we confirm the experimental result.

摘要

多溴二苯醚（PBDE）化合物源自海洋生物，来源于海洋海绵与蓝细菌或细菌之间的共生关系。PBDE 具有广泛的生物谱，因此，我们通过反应和计算研究分析了 PBDE 的结构与活性关系，以确定其作为抗癌或抗菌先导结构的潜力。从海绵中分离出了 6 种已知的 PBDE（-）；首次报道了化合物的 13 C NMR 数据，并通过理论 13 C NMR 化学位移（RMSE < 4.0 ppm）确认了其归属。在酚羟基官能团上对 （2,3,4,5-四溴-6-（3',5'-二溴-2'-羟基苯氧基）苯酚）进行甲基化和乙酰化，得到了 7 种分子（-），其中 、 、和 是新的。还报道了 和 的新晶体结构。对 进行脱溴反应得到了 9 种化合物（、、、-、、和 ），其中 是新的。脱溴产物 对人胚肾（HEK293T）细胞的 IC 8.65 ± 1.11；8.11 ± 1.43 µM 显示出显著的抑制活性。化合物 和 对革兰氏阳性 和革兰氏阴性 表现出抗菌活性，MID 为 0.078 µg/disk。4 个溴原子和 2 个酚羟基官能团的数量对抗菌活性（和 ）和细胞毒性（HEK293T）很重要。这一结果得到了前线分子轨道（FMOs）分析的支持。我们还通过分析 FMOs 和静电电荷提出了乙酰化和脱溴的可能产物，并通过实验验证了这一结果。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25bd/8588277/65fb8e943b08/molecules-26-06328-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25bd/8588277/09bb878554a1/molecules-26-06328-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25bd/8588277/76c159002996/molecules-26-06328-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25bd/8588277/118fe23c1cbf/molecules-26-06328-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25bd/8588277/a43c2c4f2205/molecules-26-06328-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25bd/8588277/aabb91dd1db0/molecules-26-06328-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25bd/8588277/ba27a68c38fa/molecules-26-06328-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25bd/8588277/7bfc90730eb8/molecules-26-06328-g007a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25bd/8588277/dee9109b4ce9/molecules-26-06328-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25bd/8588277/65fb8e943b08/molecules-26-06328-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25bd/8588277/09bb878554a1/molecules-26-06328-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25bd/8588277/76c159002996/molecules-26-06328-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25bd/8588277/118fe23c1cbf/molecules-26-06328-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25bd/8588277/a43c2c4f2205/molecules-26-06328-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25bd/8588277/aabb91dd1db0/molecules-26-06328-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25bd/8588277/ba27a68c38fa/molecules-26-06328-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25bd/8588277/7bfc90730eb8/molecules-26-06328-g007a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25bd/8588277/dee9109b4ce9/molecules-26-06328-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25bd/8588277/65fb8e943b08/molecules-26-06328-g009.jpg

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Org Lett. 2021 Jul 16;23(14):5457-5460. doi: 10.1021/acs.orglett.1c01796. Epub 2021 Jun 28.
3
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5
Structural, biological and pharmaceutical importance of antibiotic agent chloramphenicol.抗生素氯霉素的结构、生物学及药学重要性。
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6
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7
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8
Marine Natural Products from Indonesian Waters.印尼海域的海洋天然产物。
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9
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10
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