A cyclo-trimer of acetonitrile combining fluorescent property with ability to induce osteogenesis and its potential as multifunctional biomaterial
Source abstract
Abstract
A biomaterial combining fluorescent property with ability to induce osteogenesis can serve as an ideal multifunctional scaffold in bone tissue engineering. However, the frequently used fluorescent agents can only serve as imaging probes. The polymer or oligomer with a conjugated system containing nitrogen atoms will fulfill these criteria. In this study, a cyclo-trimer of acetonitrile is synthesized using a facile method, which is proved to be 4-amino-2,6-dimethylpyrimidine. The cyclo-trimer of acetonitrile demonstrates strong intrinsic photoluminescence and has the potential for in vivo imaging. The cyclo-trimer of acetonitrile shows no toxicity both in vitro and in vivo. Moreover, the cyclo-trimer of acetonitrile significantly promotes the osteogenesis of SaOS-2 cells by improving alkaline phosphatase activity, collagen type I and osteocalcin expression, as well as expressions of osteoblastic genes, and enhances the matrix mineralization of rBMSCs. Thus, the cyclo-trimer of acetonitrile synthesized in present study illustrates the employment of this kind multifunctional biomaterial in bone tissue engineering and may offer great potential in biomedical applications where bioimaging and osteogenesis are both required. Statement of significance A conjugated cyclo-trimer of acetonitrile combining intrinsic fluorescent property with ability to induce osteogenesis was reported. Different from the traditional fluorescent dye or quantum dots, which are just "imaging agents", the cyclo-trimer of acetonitrile can serve as a multifunctional biomaterial and offer great potential in biomedical applications where bioimaging and osteogenesis are both required. To our best knowledge, the fluorescent property, especially fluorescent property in vivo and the ability of this molecule to induce osteogenesis have not been reported before. Our work illustrates the employment of this kind multifunctional biomaterial in bone tissue engineering and will highlight the importance of multifunctional biomaterial in biomedical applications.
Source: europepmc · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Bone Tissue Engineering Materials · Supramolecular Self-Assembly in Materials · Luminescence and Fluorescent Materials
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (44)
Show source-provided references
1. Surface modification by allylamine plasma polymerization promotes osteogenic differentiation of human adipose-derived stem cells10.1021/am502170s ↗
2. Bone tissue engineering: a review in bone biomimetics and drug delivery strategies10.1002/btpr.246 ↗
3. Tissue engineering-technique uses body as 'bioreactor' to grow new bone10.1126/science.309.5735.683a ↗
4. A decade of progress in tissue engineering10.1038/nprot.2016.123 ↗
5. Fabrication and characterization of biomimetic multichanneled crosslinked-urethane-doped polyester tissue engineered nerve guides
6. In vivo engineering of organs: the bone bioreactor10.1073/pnas.0504705102 ↗
7. From in vitro to in situ tissue engineering10.1007/s10439-014-1022-8 ↗
8. Recent advances in bone tissue engineering scaffolds10.1016/j.tibtech.2012.07.005 ↗
9. Phage nanofibers induce vascularized osteogenesis in 3D printed bone scaffolds10.1002/adma.201400154 ↗
10. Phage as a genetically modifiable supramacromolecule in chemistry, materials and medicine10.1021/acs.accounts.5b00557 ↗
11. Enhanced physiochemical and mechanical performance of chitosan-grafted graphene oxide for superior osteoinductivity10.1002/adfm.201504141 ↗
12. Fluorescence imaging enabled urethane-doped citrate-based biodegradable elastomers10.1016/j.biomaterials.2013.02.040 ↗
13. Development of a multifunctional platform based on strong, intrinsically photoluminescent and antimicrobial silica-poly(citrates)-based hybrid biodegradable elastomers for bone regeneration10.1002/adfm.201501712 ↗
14. Quantum dots versus organic dyes as fluorescent labels10.1038/nmeth.1248 ↗
15. Quantum dot bioconjugates for imaging, labelling and sensing10.1038/nmat1390 ↗
16. Conjugated polymer nanodots as ultrastable long-term trackers to understand mesenchymal stem cell therapy in skin regeneration10.1002/adfm.201501081 ↗
17. Near-infrared emitting and pro-angiogenic electrospun conjugated polymer scaffold for optical biomaterial tracking10.1002/adfm.201500351 ↗
18. Quantum dot cytotoxicity and ways to reduce it10.1021/ar3000585 ↗
19. Cellular toxicity of inorganic nanoparticles: common aspects and guidelines for improved nanotoxicity evaluation10.1016/j.nantod.2011.08.001 ↗
20. Design strategies for fluorescent biodegradable polymeric biomaterials10.1039/C2TB00071G ↗
21. Synthesis and characterization of a cyclic polyacetonitril oligomer and its application on solid polymer electrolyte10.1016/S1452-3981(23)17277-4 ↗
22. Surface chemical gradient affects the differentiation of human adipose-derived stem cells via ERK1/2 signaling pathway10.1021/acsami.5b04635 ↗
23. Selective oligomerization of nitriles having α-hydrogen catalyzed by alkali10.1016/S1381-1169(03)00154-7 ↗
24. The trimerization of nitriles at high pressures10.1021/ja01142a028 ↗
25. Formation of 4-aminopyrimidines via the trimerization of nitriles using focused microwave heating10.1021/cc049826d ↗
26. RhCl3-catalyzed hydroboration of alkenyl nitriles10.1016/S0040-4039(03)01522-3 ↗
27. Vibrational spectroscopic investigation of tetracyanopalladate bridged two dimensional coordination polymer compounds of pyrimidine10.14233/ajchem.2013.15119 ↗
28. Infrared and Raman spectroscopic study of 4-aminopyrimidine tetracyanonickelate complexes10.1016/j.molstruc.2006.11.042 ↗
29. Multicolor conjugated polymer dots for biological fluorescence imaging10.1021/nn800590n ↗
30. Time-domain fluorescence lifetime imaging applied to biological tissue10.1039/b316456j ↗
31. A symmetrical fluorous dendron-cyanine dye-conjugated bimodal nanoprobe for quantitative 19F MRI and NIR fluorescence bioimaging10.1002/adhm.201400088 ↗
32. Development of aliphatic biodegradable photoluminescent polymers10.1073/pnas.0900004106 ↗
33. Characterization of a human osteosarcoma cell line (SaOS-2) with osteoblastic properties
34. Granulocyte-macrophage colony-stimulating factor (GM-CSF) induces the osteoblastic differentiation of the human osteosarcoma cell line SaOS-210.1007/s00223-001-2088-5 ↗
35. Silica as a morphogenetically active inorganic polymer10.1039/c3bm00001j ↗
36. Runx2 induces osteoblast and chondrocyte differentiation and enhances their migration by coupling with PI3K-Akt signaling10.1083/jcb.200401138 ↗
37. Combination of Runx2 and BMP2 increases conversion of human ligamentum flavum cells into osteoblastic cells10.5483/BMBRep.2011.44.7.446 ↗
38. X. Liu, B. Yu, Q. Huang, R. Liu, Q. Feng, Q. Cai, S. Mi, In vitro BMP-2 peptide release from thiolated chitosan based hydrogel, Int. J. Biol. Macromol. 93, Part A (2016) 314–321.10.1016/j.ijbiomac.2016.08.048 ↗
39. Development of therapeutic small-molecule fluorophore for cell transplantation10.1002/adfm.201600996 ↗
40. pH-responsive pHLIP (pH low insertion peptide) nanoclusters of superparamagnetic iron oxide nanoparticles as a tumor-selective MRI contrast agent10.1016/j.actbio.2017.03.046 ↗
41. Multi-functional nanoparticles as theranostic agents for the treatment & imaging of pancreatic cancer10.1016/j.actbio.2016.11.053 ↗
42. Systematic evaluation of multifunctional paclitaxel-loaded polymeric mixed micelles as a potential anticancer remedy to overcome multidrug resistance10.1016/j.actbio.2016.12.021 ↗
43. Rapid fabrication of carbon quantum dots as multifunctional nanovehicles for dual-modal targeted imaging and chemotherapy10.1016/j.actbio.2016.09.027 ↗
44. A bifunctional biomaterial with photothermal effect for tumor therapy and bone regeneration10.1002/adfm.201504142 ↗