• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

碳硼烷基二氢卟吩e6作为一种高效抗菌光敏剂。

Carboranyl-Chlorin e6 as a Potent Antimicrobial Photosensitizer.

作者信息

Omarova Elena O, Nazarov Pavel A, Firsov Alexander M, Strakhovskaya Marina G, Arkhipova Anastasia Yu, Moisenovich Mikhail M, Agapov Igor I, Ol'shevskaya Valentina A, Zaitsev Andrey V, Kalinin Valery N, Kotova Elena A, Antonenko Yuri N

机构信息

Belozersky Institute of Physico-Chemical Biology, Lomonosov Moscow State University, Moscow, Russia.

Biological Department, Lomonosov Moscow State University, Moscow, Russia.

出版信息

PLoS One. 2015 Nov 4;10(11):e0141990. doi: 10.1371/journal.pone.0141990. eCollection 2015.

DOI:10.1371/journal.pone.0141990
PMID:26535905
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4633095/
Abstract

Antimicrobial photodynamic inactivation is currently being widely considered as alternative to antibiotic chemotherapy of infective diseases, attracting much attention to design of novel effective photosensitizers. Carboranyl-chlorin-e6 (the conjugate of chlorin e6 with carborane), applied here for the first time for antimicrobial photodynamic inactivation, appeared to be much stronger than chlorin e6 against Gram-positive bacteria, such as Bacillus subtilis, Staphyllococcus aureus and Mycobacterium sp. Confocal fluorescence spectroscopy and membrane leakage experiments indicated that bacteria cell death upon photodynamic treatment with carboranyl-chlorin-e6 is caused by loss of cell membrane integrity. The enhanced photobactericidal activity was attributed to the increased accumulation of the conjugate by bacterial cells, as evaluated both by centrifugation and fluorescence correlation spectroscopy. Gram-negative bacteria were rather resistant to antimicrobial photodynamic inactivation mediated by carboranyl-chlorin-e6. Unlike chlorin e6, the conjugate showed higher (compared to the wild-type strain) dark toxicity with Escherichia coli ΔtolC mutant, deficient in TolC-requiring multidrug efflux transporters.

摘要

抗菌光动力灭活目前被广泛认为是感染性疾病抗生素化疗的替代方法，这吸引了人们对新型有效光敏剂设计的高度关注。首次用于抗菌光动力灭活的碳硼烷基二氢卟吩 - e6（二氢卟吩e6与碳硼烷的共轭物），对革兰氏阳性菌，如枯草芽孢杆菌、金黄色葡萄球菌和分枝杆菌属，似乎比二氢卟吩e6的抗菌能力强得多。共聚焦荧光光谱和膜渗漏实验表明，用碳硼烷基二氢卟吩 - e6进行光动力处理后细菌细胞死亡是由细胞膜完整性丧失引起的。通过离心和荧光相关光谱评估，增强的光杀菌活性归因于细菌细胞对共轭物积累的增加。革兰氏阴性菌对碳硼烷基二氢卟吩 - e6介导的抗菌光动力灭活相当耐药。与二氢卟吩e6不同，该共轭物对缺乏需要TolC的多药外排转运蛋白的大肠杆菌ΔtolC突变体显示出更高（与野生型菌株相比）的暗毒性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/508b/4633095/9a26827c2816/pone.0141990.g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/508b/4633095/02702f5a08a5/pone.0141990.g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/508b/4633095/ed973048f09b/pone.0141990.g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/508b/4633095/a7f25eeaef21/pone.0141990.g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/508b/4633095/b949224609b6/pone.0141990.g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/508b/4633095/26f90c0efe8b/pone.0141990.g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/508b/4633095/d0f776929a86/pone.0141990.g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/508b/4633095/7da84ff00355/pone.0141990.g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/508b/4633095/9a26827c2816/pone.0141990.g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/508b/4633095/02702f5a08a5/pone.0141990.g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/508b/4633095/ed973048f09b/pone.0141990.g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/508b/4633095/a7f25eeaef21/pone.0141990.g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/508b/4633095/b949224609b6/pone.0141990.g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/508b/4633095/26f90c0efe8b/pone.0141990.g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/508b/4633095/d0f776929a86/pone.0141990.g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/508b/4633095/7da84ff00355/pone.0141990.g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/508b/4633095/9a26827c2816/pone.0141990.g008.jpg

相似文献

1
Carboranyl-Chlorin e6 as a Potent Antimicrobial Photosensitizer.碳硼烷基二氢卟吩e6作为一种高效抗菌光敏剂。
PLoS One. 2015 Nov 4;10(11):e0141990. doi: 10.1371/journal.pone.0141990. eCollection 2015.
2
Polycationic photosensitizer conjugates: effects of chain length and Gram classification on the photodynamic inactivation of bacteria.聚阳离子光敏剂缀合物：链长和革兰氏分类对细菌光动力灭活的影响。
J Antimicrob Chemother. 2002 Jun;49(6):941-51. doi: 10.1093/jac/dkf053.
3
Photodynamic activity of the boronated chlorin e6 amide in artificial and cellular membranes.硼化二氢卟吩e6酰胺在人工膜和细胞膜中的光动力活性。
Biochim Biophys Acta. 2014 Mar;1838(3):793-801. doi: 10.1016/j.bbamem.2013.11.012. Epub 2013 Nov 25.
4
Chlorin e6 conjugated chitosan as an efficient photoantimicrobial agent.二氢卟吩e6共轭壳聚糖作为一种高效的光抗菌剂。
Int J Biol Macromol. 2021 Jul 31;183:1309-1316. doi: 10.1016/j.ijbiomac.2021.05.085. Epub 2021 May 14.
5
Protease-stable polycationic photosensitizer conjugates between polyethyleneimine and chlorin(e6) for broad-spectrum antimicrobial photoinactivation.用于广谱抗菌光灭活的聚乙烯亚胺与二氢卟吩（e6）之间的蛋白酶稳定型聚阳离子光敏剂缀合物。
Antimicrob Agents Chemother. 2006 Apr;50(4):1402-10. doi: 10.1128/AAC.50.4.1402-1410.2006.
6
The susceptibility of anaerobic bacteria isolated from periodontal diseases to photodynamic inactivation with Fotolon (chlorin e6).从牙周疾病中分离出的厌氧菌对使用Fotolon（二氢卟吩e6）进行光动力灭活的敏感性。
Pol J Microbiol. 2005;54(4):305-10.
7
A conjugate of chlorin e6 and cationic amphipathic peptoid: a dual antimicrobial and anticancer photodynamic therapy agent.氯吡咯并[3,4-b]吡咯-1,4-二酮与阳离子两亲性肽的偶联物：一种兼具抗菌和抗癌作用的光动力治疗剂。
Photochem Photobiol Sci. 2023 Mar;22(3):655-667. doi: 10.1007/s43630-022-00343-8. Epub 2022 Dec 8.
8
Photobiological characteristics of chlorophyll a derivatives as microbial PDT agents.叶绿素a衍生物作为微生物光动力治疗剂的光生物学特性。
Photochem Photobiol Sci. 2014 Aug;13(8):1137-45. doi: 10.1039/c3pp50376c.
9
Synthesis and properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl] chlorin as potential broad-spectrum antimicrobial photosensitizers.5,10,15,20-四[4-(3-N,N-二甲基氨基丙氧基)苯基]二氢卟吩作为潜在的广谱抗菌光敏剂的合成与性质
J Photochem Photobiol B. 2016 May;158:243-51. doi: 10.1016/j.jphotobiol.2016.02.021. Epub 2016 Mar 4.
10
Improved photoinactivation of gram-negative and gram-positive methicillin-resistant bacterial strains using a new near-infrared absorbing meso-tetrahydroporphyrin: a comparative study with a chlorine e6 photosensitizer photolon.使用一种新型近红外吸收中-四氢卟啉改善革兰氏阴性和革兰氏阳性耐甲氧西林菌株的光灭活：与氯e6光敏剂Photolon的比较研究
Methods Find Exp Clin Pharmacol. 2008 Mar;30(2):129-33. doi: 10.1358/mf.2008.30.2.1165448.

引用本文的文献

1
Activity of Organoboron Compounds against Biofilm-Forming Pathogens.有机硼化合物对生物膜形成病原体的活性。
Antibiotics (Basel). 2024 Sep 29;13(10):929. doi: 10.3390/antibiotics13100929.
2
Multidrug Resistance Pumps as a Keystone of Bacterial Resistance.多药耐药泵作为细菌耐药性的关键因素
Moscow Univ Biol Sci Bull. 2022;77(4):193-200. doi: 10.3103/S009639252204006X. Epub 2023 Feb 20.
3
MDR Pumps as Crossroads of Resistance: Antibiotics and Bacteriophages.多重耐药泵作为耐药性的交叉点：抗生素与噬菌体

本文引用的文献

1
Evaluation of the interplay among the charge of porphyrinic photosensitizers, lipid oxidation and photoinactivation efficiency in Escherichia coli.卟啉类光敏剂电荷、脂质氧化与大肠杆菌光灭活效率之间相互作用的评估
J Photochem Photobiol B. 2014 Dec;141:145-53. doi: 10.1016/j.jphotobiol.2014.08.024. Epub 2014 Oct 13.
2
In vitro studies of different irradiation conditions for Photodynamic inactivation of Helicobacter pylori.幽门螺杆菌光动力灭活不同照射条件的体外研究
J Photochem Photobiol B. 2014 Dec;141:113-8. doi: 10.1016/j.jphotobiol.2014.09.015. Epub 2014 Oct 12.
3
A mitochondria-targeted protonophoric uncoupler derived from fluorescein.
Antibiotics (Basel). 2022 May 30;11(6):734. doi: 10.3390/antibiotics11060734.
4
Cobalt Bis-Dicarbollide Enhances Antibiotics Action towards Planktonic Growth Due to Cell Envelopes Disruption.钴双二碳硼烷通过破坏细胞膜增强抗生素对浮游生长的作用。
Pharmaceuticals (Basel). 2022 Apr 26;15(5):534. doi: 10.3390/ph15050534.
5
Synthesis and Structure of the Bis- and Tris-Polyhedral Hybrid Carboranoclathrochelates with Functionalizing Biorelevant Substituents-The Derivatives of Propargylamine Iron(II) Clathrochelates with Terminal Triple C≡C Bond(s).具有功能化生物相关取代基的双多面体和三多面体杂化碳硼烷笼形螯合物的合成与结构——末端含三键（C≡C）的炔丙胺铁（II）笼形螯合物的衍生物
Molecules. 2021 Jun 14;26(12):3635. doi: 10.3390/molecules26123635.
6
Fluorinated maleimide-substituted porphyrins and chlorins: synthesis and characterization.氟化马来酰亚胺取代的卟啉和二氢卟吩：合成与表征
Beilstein J Org Chem. 2019 Nov 13;15:2704-2709. doi: 10.3762/bjoc.15.263. eCollection 2019.
7
Antimicrobial Photodynamic Inactivation Mediated by Rose Bengal and Erythrosine Is Effective in the Control of Food-Related Bacteria in Planktonic and Biofilm States.Rose Bengal 和赤藓红介导的抗菌光动力失活在控制浮游和生物膜状态下与食物相关的细菌方面是有效的。
Molecules. 2018 Sep 7;23(9):2288. doi: 10.3390/molecules23092288.
8
Mitochondria-targeted antioxidants as highly effective antibiotics.线粒体靶向抗氧化剂作为高效抗生素。
Sci Rep. 2017 May 3;7(1):1394. doi: 10.1038/s41598-017-00802-8.
9
Efficient access to βvinylporphyrin derivatives via palladium cross coupling of β-bromoporphyrins with -tosylhydrazones.通过β-溴卟啉与对甲苯磺酰腙的钯交叉偶联高效合成β-乙烯基卟啉衍生物。
Beilstein J Org Chem. 2017 Jan 30;13:195-202. doi: 10.3762/bjoc.13.22. eCollection 2017.
一种源自荧光素的线粒体靶向质子载体解偶联剂。
Chem Commun (Camb). 2014 Dec 18;50(97):15366-9. doi: 10.1039/c4cc04996a. Epub 2014 Oct 28.
4
AcrB, AcrD, and MdtABC multidrug efflux systems are involved in enterobactin export in Escherichia coli.AcrB、AcrD和MdtABC多药外排系统参与大肠杆菌中铁载体肠杆菌素的输出。
PLoS One. 2014 Sep 26;9(9):e108642. doi: 10.1371/journal.pone.0108642. eCollection 2014.
5
Synthesis and biological evaluation of new BSH-conjugated chlorin derivatives as agents for both photodynamic therapy and boron neutron capture therapy of cancer.新型BSH共轭二氢卟吩衍生物作为癌症光动力治疗和硼中子俘获治疗药物的合成及生物学评价
J Photochem Photobiol B. 2014 Nov;140:140-9. doi: 10.1016/j.jphotobiol.2014.07.008. Epub 2014 Jul 22.
6
The potential for photodynamic therapy in the treatment of localized infections.光动力疗法在局部感染治疗中的应用潜力。
Photodiagnosis Photodyn Ther. 2005 Dec;2(4):247-62. doi: 10.1016/S1572-1000(05)00099-2. Epub 2005 Oct 27.
7
Evaluation of antibacterial properties of novel phthalocyanines against Escherichia coli--comparison of analytical methods.新型酞菁对大肠杆菌抗菌性能的评估——分析方法比较
J Photochem Photobiol B. 2014 Sep 5;138:230-9. doi: 10.1016/j.jphotobiol.2014.04.014. Epub 2014 Apr 30.
8
Photobiological characteristics of chlorophyll a derivatives as microbial PDT agents.叶绿素a衍生物作为微生物光动力治疗剂的光生物学特性。
Photochem Photobiol Sci. 2014 Aug;13(8):1137-45. doi: 10.1039/c3pp50376c.
9
Unsaturated lipids protect the integral membrane peptide gramicidin A from singlet oxygen.不饱和脂质可保护整合膜肽短杆菌肽 A 免受单线态氧的侵害。
FEBS Lett. 2014 May 2;588(9):1590-5. doi: 10.1016/j.febslet.2014.02.046. Epub 2014 Mar 5.
10
Influence of external bacterial structures on the efficiency of photodynamic inactivation by a cationic porphyrin.外部细菌结构对阳离子卟啉光动力灭活效率的影响。
Photochem Photobiol Sci. 2014 Apr;13(4):680-90. doi: 10.1039/c3pp50408e.