Design and synthesis of biodegradable nonconjugated SSPAMAM dendrimers with unexpected Deep-red/NIR emission and cell membrane targeting ability for biological imaging

Fluorescent non-conjugated polymers without any π-aromatic building blocks are of great significance in biological applications due to low cytotoxicity and good biocompatibility. However, it is still a great challenge to achieve bright and deep-red/near-infrared (NIR) emissions. Herein, we have desi...

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Main Authors: Xiao-lin Guan, Xue-qin Yang, Shou-jun Lai, Yuan-yuan Ding, Jing-yu Wei, Jia-ming Zhang, Li-yuan Zhang, Cheng-hao Li, Jin-hui Tong, Zi-qiang Lei
Format: Article
Language:English
Published: Elsevier 2022-09-01
Series:Materials & Design
Subjects:
Online Access:http://www.sciencedirect.com/science/article/pii/S0264127522006049
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author Xiao-lin Guan
Xue-qin Yang
Shou-jun Lai
Yuan-yuan Ding
Jing-yu Wei
Jia-ming Zhang
Li-yuan Zhang
Cheng-hao Li
Jin-hui Tong
Zi-qiang Lei
author_facet Xiao-lin Guan
Xue-qin Yang
Shou-jun Lai
Yuan-yuan Ding
Jing-yu Wei
Jia-ming Zhang
Li-yuan Zhang
Cheng-hao Li
Jin-hui Tong
Zi-qiang Lei
author_sort Xiao-lin Guan
collection DOAJ
description Fluorescent non-conjugated polymers without any π-aromatic building blocks are of great significance in biological applications due to low cytotoxicity and good biocompatibility. However, it is still a great challenge to achieve bright and deep-red/near-infrared (NIR) emissions. Herein, we have designed and synthesized a series of deep-red/NIR non-conjugated polymers with aggregation-induced emission based on disulfide-linked poly(amidoamine) (SSPAMAM) dendrimers, which exhibit excellent biodegradation for bioimaging. These SSPAMAM dendrimers (G0.5-G2.0) containing disulfide bonds in their backbone were synthesized in high yield by incorporating cystamine instead of common diacrylamide. Unexpectedly, the SSPAMAM dendrimers prepared exhibited bright and excitation dependent multicolor-tunable emission. More interestingly, G2.0 SSPAMAM showed a deep-red/NIR emission (λem = 625 nm with a shoulder at 800 nm) originated from an extraordinarily rigid and compact conformation via strong intramolecular hydrogen bonds. Meanwhile, these dendrimers displayed excellent biodegradability because of the large number of disulfide linkages in backbone. Due to the excellent specific cytomembrane location, SSPAMAM dendrimers can be used as a potential cell membrane imaging reagent for multi-color (blue, green, and deep-red) imaging. Furthermore, they could also be used in zebrafish for bioimaging. This investigation has expanded the applications of fluorescent non-conjugated polymers to the field of long-wavelength in vivo biological imaging.
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spelling doaj.art-d5412c9811cd4732a542ce7a7d77062e2022-12-22T02:16:12ZengElsevierMaterials & Design0264-12752022-09-01221110982Design and synthesis of biodegradable nonconjugated SSPAMAM dendrimers with unexpected Deep-red/NIR emission and cell membrane targeting ability for biological imagingXiao-lin Guan0Xue-qin Yang1Shou-jun Lai2Yuan-yuan Ding3Jing-yu Wei4Jia-ming Zhang5Li-yuan Zhang6Cheng-hao Li7Jin-hui Tong8Zi-qiang Lei9Key Laboratory of Eco-Environment-Related Polymer Materials Ministry of Education, Key Laboratory of Polymer Materials Ministry of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, PR China; Corresponding authors.Key Laboratory of Eco-Environment-Related Polymer Materials Ministry of Education, Key Laboratory of Polymer Materials Ministry of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, PR ChinaCollege of Chemical Engineering, Lanzhou University of Arts and Science, Lanzhou, Gansu 730000, PR China; Corresponding authors.Key Laboratory of Eco-Environment-Related Polymer Materials Ministry of Education, Key Laboratory of Polymer Materials Ministry of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, PR ChinaKey Laboratory of Eco-Environment-Related Polymer Materials Ministry of Education, Key Laboratory of Polymer Materials Ministry of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, PR ChinaKey Laboratory of Eco-Environment-Related Polymer Materials Ministry of Education, Key Laboratory of Polymer Materials Ministry of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, PR ChinaKey Laboratory of Eco-Environment-Related Polymer Materials Ministry of Education, Key Laboratory of Polymer Materials Ministry of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, PR ChinaKey Laboratory of Traditional Chinese Medicine Prevention and Treatment, Gansu University of Traditional Chinese Medicine, Lanzhou 730000, ChinaKey Laboratory of Eco-Environment-Related Polymer Materials Ministry of Education, Key Laboratory of Polymer Materials Ministry of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, PR ChinaKey Laboratory of Eco-Environment-Related Polymer Materials Ministry of Education, Key Laboratory of Polymer Materials Ministry of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, PR ChinaFluorescent non-conjugated polymers without any π-aromatic building blocks are of great significance in biological applications due to low cytotoxicity and good biocompatibility. However, it is still a great challenge to achieve bright and deep-red/near-infrared (NIR) emissions. Herein, we have designed and synthesized a series of deep-red/NIR non-conjugated polymers with aggregation-induced emission based on disulfide-linked poly(amidoamine) (SSPAMAM) dendrimers, which exhibit excellent biodegradation for bioimaging. These SSPAMAM dendrimers (G0.5-G2.0) containing disulfide bonds in their backbone were synthesized in high yield by incorporating cystamine instead of common diacrylamide. Unexpectedly, the SSPAMAM dendrimers prepared exhibited bright and excitation dependent multicolor-tunable emission. More interestingly, G2.0 SSPAMAM showed a deep-red/NIR emission (λem = 625 nm with a shoulder at 800 nm) originated from an extraordinarily rigid and compact conformation via strong intramolecular hydrogen bonds. Meanwhile, these dendrimers displayed excellent biodegradability because of the large number of disulfide linkages in backbone. Due to the excellent specific cytomembrane location, SSPAMAM dendrimers can be used as a potential cell membrane imaging reagent for multi-color (blue, green, and deep-red) imaging. Furthermore, they could also be used in zebrafish for bioimaging. This investigation has expanded the applications of fluorescent non-conjugated polymers to the field of long-wavelength in vivo biological imaging.http://www.sciencedirect.com/science/article/pii/S0264127522006049Disulfide-linked poly(amidoamine)Non-conjugated polymersDeep-red/NIR emissionBiodegradationBioimaging
spellingShingle Xiao-lin Guan
Xue-qin Yang
Shou-jun Lai
Yuan-yuan Ding
Jing-yu Wei
Jia-ming Zhang
Li-yuan Zhang
Cheng-hao Li
Jin-hui Tong
Zi-qiang Lei
Design and synthesis of biodegradable nonconjugated SSPAMAM dendrimers with unexpected Deep-red/NIR emission and cell membrane targeting ability for biological imaging
Materials & Design
Disulfide-linked poly(amidoamine)
Non-conjugated polymers
Deep-red/NIR emission
Biodegradation
Bioimaging
title Design and synthesis of biodegradable nonconjugated SSPAMAM dendrimers with unexpected Deep-red/NIR emission and cell membrane targeting ability for biological imaging
title_full Design and synthesis of biodegradable nonconjugated SSPAMAM dendrimers with unexpected Deep-red/NIR emission and cell membrane targeting ability for biological imaging
title_fullStr Design and synthesis of biodegradable nonconjugated SSPAMAM dendrimers with unexpected Deep-red/NIR emission and cell membrane targeting ability for biological imaging
title_full_unstemmed Design and synthesis of biodegradable nonconjugated SSPAMAM dendrimers with unexpected Deep-red/NIR emission and cell membrane targeting ability for biological imaging
title_short Design and synthesis of biodegradable nonconjugated SSPAMAM dendrimers with unexpected Deep-red/NIR emission and cell membrane targeting ability for biological imaging
title_sort design and synthesis of biodegradable nonconjugated sspamam dendrimers with unexpected deep red nir emission and cell membrane targeting ability for biological imaging
topic Disulfide-linked poly(amidoamine)
Non-conjugated polymers
Deep-red/NIR emission
Biodegradation
Bioimaging
url http://www.sciencedirect.com/science/article/pii/S0264127522006049
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