Citation: Zhang Qian, Dong Xue, Wang Kun-Peng, Zhu Ting-Ting, Sun Feng-Nan, Meng Shu-Xian, Feng Ya-Qing. Glycine-conjugated porphyrin fluorescent probe with iRGD for live cell imaging[J]. Chinese Chemical Letters, ;2017, 28(4): 777-781. doi: 10.1016/j.cclet.2017.03.001 shu

Glycine-conjugated porphyrin fluorescent probe with iRGD for live cell imaging

Zhang Qian ^a,b ,
Dong Xue ^a,b ,
Wang Kun-Peng ^a,b ,
Zhu Ting-Ting ^a,b ,
Sun Feng-Nan ^a,b ,
Meng Shu-Xian ^a,b,, ,
Feng Ya-Qing ^a,b

a.
School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China
b.
Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), Tianjin 300072, China

Corresponding author: Meng Shu-Xian, msxmail@tju.edu.cn
Received Date: 3 January 2017
Revised Date: 13 January 2017
Accepted Date: 2 March 2017
Available Online: 4 April 2017

Figures(5)

A porphyrin modified by glycine has been synthesized and developed as a near-infrared(NIR) fluorescence probe to detect tumor.Porphyrins'longwavelength emission at ~650 nm can efficiently avoid the spectral crosstalk with Spontaneous fluorescence in the visible light region.A disulfide-based cyclic RGD peptide named iRGD c(CRGDKGPDC), a tumor homing peptide, harbors a cryptic C-end Rule (CendR)motif that is responsible for neuropilin-1(NRP-1) binding and for triggering extravasation and tumor penetration of the peptide to improve the imaging sensitivity and therapeutic efficacy.We used N-hydroxy succinimide as an activator to introduce the glycine methyl ester to detect tumor.We got a porphyrin modified by glycine.The affinity between probe and tumor cell entered GLC-82 cells(human glandular lung cancer cell line)can be observed by Confocal Microscope.The toxicity of probe has been identified by MTT Assay.The summary has been gotten that the porphyrins were nontoxic to GLC-82 cells and glycine modified porphyrin has a good affinity with GLC-82 cells under the iRGD function by our experiment.
- Fluorescence probe,
- iRGD,
- Glycine,
- Porphyrin,
- Near-infrared
1. [1]
  Tanaka S., Kizaka-Kondoh S.. Development of fluorescent in vivo imaging probes for cancers[J]. Gan to Kagaku Ryoho, 2008,35:1272-1276.
2. [2]
  Zhao H.Y., Li Y.M., Gong T.J., Guo Q.X.. A highly selective and easy-to-synthesize Zn(Ⅱ) fluorescent probe based on 6-methoxyquinolin[J]. Chin.Chem.Lett., 2011,22:1013-1016. doi: 10.1016/j.cclet.2011.03.007
3. [3]
  Gao Y., Li J.L., Shi Z.. Synthesis and application of rhodamine-based fluorescent probe dyes with spacer linker arm[J]. Chin.Chem.Lett., 2007,18:667-669. doi: 10.1016/j.cclet.2007.04.007
4. [4]
  Sun C.L., Cai J., Chen J.Q.. The synthesis of a novel near-infrared fluorescent probe and its application in imaging of living cells[J]. Appl.Biochem. Biotechnol., 2015,175:1644-1650. doi: 10.1007/s12010-014-1398-9
5. [5]
  Shao F.W., Weissleder R., Hilderbrand S.A.. Monofunctional carbocyanine dyes for bio-and bioorthogonal conjugation[J]. Bioconjugate Chem., 2008,19:2487-2491. doi: 10.1021/bc800417b
6. [6]
  Zhang X.F., Xiao Y., Qi J.. Long-wavelength photostable, two-photon excitable bodipy fluorophores readily modifiable for molecular probes[J]. J.Org. Chem., 2013,78:9153-9160. doi: 10.1021/jo401379g
7. [7]
  Li P., Tang B., Xing Y.L.. A near-infrared fluorescent probe for lipid hydroperoxides in living cells[J]. Analyst, 2008,133:1409-1415. doi: 10.1039/b802836b
8. [8]
  Kojima H.. Development of near-infrared fluorescent probes for in vivo imaging[J]. Yakugaku Zasshi., 2008,128:1653-1663. doi: 10.1248/yakushi.128.1653
9. [9]
  Li D.H., Diao J.L., Yu K.G., Zhou C.H.. Synthesis and anticancer activities of porphyrin induced anticancer drugs[J]. Chin.Chem.Lett., 2007,18:1331-1334. doi: 10.1016/j.cclet.2007.09.012
10. [10]
  Choi J., Kim H., Choi Y.. Theranostic nanoparticles for enzyme-activatable fluorescence imaging and photodynamic/chemo dual therapy of triple-negative breast cancer[J]. Quant.Imaging Med.Surg., 2015,5:656-664.
11. [11]
  Giuntini F., Chauhan V.M., Aylott J.W.. Conjugatable water-soluble Pt(Ⅱ) and Pd(Ⅱ)porphyrin complexes:novel nano-and molecular probes for optical oxygen tension measurement in tissue engineering[J]. Photochem.Photobiol. Sci., 2014,13:1039-1051. doi: 10.1039/c4pp00026a
12. [12]
  Amin M., Mansourian M., Koning G.A.. Development of a novel cyclic RGD peptide for multiple targeting approaches of liposomes to tumor region[J]. J. Control.Release, 2015,220:308-315. doi: 10.1016/j.jconrel.2015.10.039
13. [13]
  Beer A.J., Schwaiger M.. Imaging of integrin ανβ3 expression[J]. Cancer Metastasis Rev., 2008,27:631-644. doi: 10.1007/s10555-008-9158-3
14. [14]
  Luo M.Y., Chen M.Z., Lee I.. α_Ibβ₃ modeling simulation and design of cyclic RGD peptide[J]. Chin.J.Biotechnol., 2008,24:297-301. doi: 10.1016/S1872-2075(08)60015-1
15. [15]
  Simón-Gracia L., Hunt H., Scodeller P.. iRGD peptide conjugation potentiates intraperitoneal tumor delivery of paclitaxel with polymersomes[J]. Biomaterials, 2016,104:247-257. doi: 10.1016/j.biomaterials.2016.07.023
16. [16]
  Hamilton A.M., Aidoudi-Ahmed S., Sharma S.. Nanoparticles coated with the tumor-penetrating peptide iRGD reduce experimental breast cancer metastasis in the brain[J]. J.Mol.Med., 2015,93:991-1001. doi: 10.1007/s00109-015-1279-x
17. [17]
  Sugahara K.N., Braun G.B., de Mendoza T.H.. Tumor-penetrating iRGD peptide inhibits metastasis[J]. Mol.Cancer Ther., 2015,14:120-128.
18. [18]
  Chilakamarthi U., Kandhadi J., Gunda S.. Synthesis and functional characterization of a fluorescent peptide probe for non invasive imaging of collagen in live tissues[J]. Exp.Cell Res., 2014,327:91-101. doi: 10.1016/j.yexcr.2014.05.005
19. [19]
  Wang L.S., Jiang X.S., Wang H., Cheng S.X., Zhuo R.X.. Preparation and cytotoxicity of novel aliphatic polycarbonate synthesized from dihydroxyacetone[J]. Chin.Chem.Lett., 2005,16:572-574.
1. [1]
  Yudi Cheng , Xiao Wang , Jiao Chen , Zihan Zhang , Jiadong Ou , Mengyao She , Fulin Chen , Jianli Li . A near-infrared fluorescent probe for visualizing transformation pathway of Cys/Hcy and H₂S and its applications in living system. Chinese Chemical Letters, 2024, 35(5): 109156-. doi: 10.1016/j.cclet.2023.109156
2. [2]
  Dandan Tang , Ningge Xu , Yuyang Fu , Wei Peng , Jinsheng Wu , Heng Liu , Fabiao Yu . Rationally designed an innovative proximity labeling near-infrared fluorogenic probe for imaging of peroxynitrite in acute lung injury. Chinese Chemical Letters, 2025, 36(5): 110082-. doi: 10.1016/j.cclet.2024.110082
3. [3]
  Meiling Zhao , Yao Lu , Yutao Zhang , Haoyun Xue , Zhiqian Guo . Ultra-high signal-to-noise ratio near-infrared chemiluminescent probe for in vivo sensing singlet oxygen. Chinese Chemical Letters, 2025, 36(5): 110105-. doi: 10.1016/j.cclet.2024.110105
4. [4]
  Chen Lu , Zefeng Yu , Jing Cao . Advancement in porphyrin/phthalocyanine compounds-based perovskite solar cells. Chinese Journal of Structural Chemistry, 2024, 43(3): 100240-100240. doi: 10.1016/j.cjsc.2024.100240
5. [5]
  Wenping Dong , Mo Ma , Jingkang Li , Lanlan Xu , Dejiang Gao , Pinyi Ma , Daqian Song . Near-infrared fluorescent probe with large Stokes shift and long emission wavelength for rapid diagnosis of lung cancer via aerosol inhalation delivery. Chinese Chemical Letters, 2025, 36(5): 110147-. doi: 10.1016/j.cclet.2024.110147
6. [6]
  Yupeng Liu , Hui Wang , Songnan Qu . Review on near-infrared absorbing/emissive carbon dots: From preparation to multi-functional application. Chinese Chemical Letters, 2025, 36(5): 110618-. doi: 10.1016/j.cclet.2024.110618
7. [7]
  Gongcheng Ma , Qihang Ding , Yuding Zhang , Yue Wang , Jingjing Xiang , Mingle Li , Qi Zhao , Saipeng Huang , Ping Gong , Jong Seung Kim . Palladium-free chemoselective probe for in vivo fluorescence imaging of carbon monoxide. Chinese Chemical Letters, 2024, 35(9): 109293-. doi: 10.1016/j.cclet.2023.109293
8. [8]
  Wenxiang Ma , Xinyu He , Tianyi Chen , De-Li Ma , Hongzheng Chen , Chang-Zhi Li . Near-infrared non-fused electron acceptors for efficient organic photovoltaics. Chinese Chemical Letters, 2024, 35(4): 109099-. doi: 10.1016/j.cclet.2023.109099
9. [9]
  Yihao Zhang , Yang Jiao , Xianchao Jia , Qiaojia Guo , Chunying Duan . Highly effective self-assembled porphyrin MOCs nanomaterials for enhanced photodynamic therapy in tumor. Chinese Chemical Letters, 2024, 35(5): 108748-. doi: 10.1016/j.cclet.2023.108748
10. [10]
  Changhui Yu , Peng Shang , Huihui Hu , Yuening Zhang , Xujin Qin , Linyu Han , Caihe Liu , Xiaohan Liu , Minghua Liu , Yuan Guo , Zhen Zhang . Evolution of template-assisted two-dimensional porphyrin chiral grating structure by directed self-assembly using chiral second harmonic generation microscopy. Chinese Chemical Letters, 2024, 35(10): 109805-. doi: 10.1016/j.cclet.2024.109805
11. [11]
  Jianhui Yin , Wenjing Huang , Changyong Guo , Chao Liu , Fei Gao , Honggang Hu . Tryptophan-specific peptide modification through metal-free photoinduced N-H alkylation employing N-aryl glycines. Chinese Chemical Letters, 2024, 35(6): 109244-. doi: 10.1016/j.cclet.2023.109244
12. [12]
  Haixian Ren , Yuting Du , Xiaojing Yang , Fangjun Huo , Le Zhang , Caixia Yin . Development of ESIPT-based specific fluorescent probes for bioactive species based on the protection-deprotection of the hydroxyl. Chinese Chemical Letters, 2025, 36(2): 109867-. doi: 10.1016/j.cclet.2024.109867
13. [13]
  Yuqing Wang , Zhemin Li , Qingjun Lu , Qizhao Li , Jiaxin Luo , Chengjie Li , Yongshu Xie . Solar cells based on doubly concerted companion dyes with the efficiencies modulated by inserting an ethynyl group at different positions. Chinese Chemical Letters, 2024, 35(5): 109093-. doi: 10.1016/j.cclet.2023.109093
14. [14]
  Boran Cheng , Lei Cao , Chen Li , Fang-Yi Huo , Qian-Fang Meng , Ganglin Tong , Xuan Wu , Lin-Lin Bu , Lang Rao , Shubin Wang . Fluorine-doped carbon quantum dots with deep-red emission for hypochlorite determination and cancer cell imaging. Chinese Chemical Letters, 2024, 35(6): 108969-. doi: 10.1016/j.cclet.2023.108969
15. [15]
  Zihong Li , Jie Cheng , Ping Huang , Guoliang Wu , Weiying Lin . Activatable photoacoustic bioprobe for visual detection of aging in vivo. Chinese Chemical Letters, 2024, 35(4): 109153-. doi: 10.1016/j.cclet.2023.109153
16. [16]
  Linfang ZHANG , Wenzhu YIN , Gui YIN . A 2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran-based near-infrared fluorescence probe for the detection of hydrogen sulfide and imaging of living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 540-548. doi: 10.11862/CJIC.20240405
17. [17]
  Yang Liu , Leilei Zhang , Kaixuan Liu , Ling-Ling Wu , Hai-Yu Hu . Penicillin G acylase-responsive near-infrared fluorescent probe: Unravelling biofilm regulation and combating bacterial infections. Chinese Chemical Letters, 2024, 35(11): 109759-. doi: 10.1016/j.cclet.2024.109759
18. [18]
  Huamei Zhang , Jingjing Liu , Mingyue Li , Shida Ma , Xucong Zhou , Aixia Meng , Weina Han , Jin Zhou . Imaging polarity changes in pneumonia and lung cancer using a lipid droplet-targeted near-infrared fluorescent probe. Chinese Chemical Letters, 2024, 35(12): 110020-. doi: 10.1016/j.cclet.2024.110020
19. [19]
  Hui Peng , Xiao Wang , Weiguo Huang , Shuiyue Yu , Linghang Kong , Qilin Wei , Jialong Zhao , Bingsuo Zou . Efficient tunable visible and near-infrared emission in Sb³⁺/Sm³⁺-codoped Cs₂NaLuCl₆ for near-infrared light-emitting diode, triple-mode fluorescence anti-counterfeiting and information encryption. Chinese Chemical Letters, 2024, 35(11): 109462-. doi: 10.1016/j.cclet.2023.109462
20. [20]
  Lixian Fu , Yiyun Tan , Yue Ding , Weixia Qing , Yong Wang . Water–soluble and polarity–sensitive near–infrared fluorescent probe for long–time specific cancer cell membranes imaging and C. Elegans label. Chinese Chemical Letters, 2024, 35(4): 108886-. doi: 10.1016/j.cclet.2023.108886

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(823)
HTML views(39)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142