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通过铜催化的叠氮-炔环加成反应（CuAAC）用β-环糊精单元对PAMAM G1树枝状大分子表面进行高效修饰：对水溶性和细胞毒性的影响

Efficient modification of PAMAM G1 dendrimer surface with β-cyclodextrin units by CuAAC: impact on the water solubility and cytotoxicity.

作者信息

Sorroza-Martínez Kendra, González-Méndez Israel, Martínez-Serrano Ricardo D, Solano José D, Ruiu Andrea, Illescas Javier, Zhu Xiao Xia, Rivera Ernesto

机构信息

Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México Circuito Exterior, Ciudad Universitaria CP 04510 México City México

Facultad de Química, Departamento de Biología, Universidad Nacional Autónoma de México Circuito Exterior, Ciudad Universitaria CP 04510 México City México.

出版信息

RSC Adv. 2020 Jul 7;10(43):25557-25566. doi: 10.1039/d0ra02574g. eCollection 2020 Jul 3.

DOI:10.1039/d0ra02574g
PMID:35518581
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9055266/
Abstract

The toxicity of the poly(amidoamine) dendrimers (PAMAM) caused by the peripheral amino groups has been a limitation for their use as drug carriers in clinical applications. In this work, we completely modified the periphery of PAMAM dendrimer generation 1 (PAMAM G1) with β-cyclodextrin (β-CD) units through the Cu(i)-catalyzed azide-alkyne cycloaddition (CuAAC) to obtain the PAMAM G1-β-CD dendrimer with high yield. The PAMAM G1-β-CD was characterized by H- and C-NMR and mass spectrometry studies. Moreover, the PAMAM G1-β-CD dendrimer showed remarkably higher water solubility than native β-CD. Finally, we studied the toxicity of PAMAM G1-β-CD dendrimer in four different cell lines, human breast cancer cells (MCF-7 and MDA-MB-231), human cervical adenocarcinoma cancer cells (HeLa) and pig kidney epithelial cells (LLC-PK1). The PAMAM G1-β-CD dendrimer did not present any cytotoxicity in cell lines tested which shows the potentiality of this new class of dendrimers.

摘要

聚（酰胺胺）树枝状大分子（PAMAM）由外围氨基引起的毒性一直是其在临床应用中作为药物载体使用的限制因素。在这项工作中，我们通过铜（I）催化的叠氮化物-炔烃环加成反应（CuAAC）用β-环糊精（β-CD）单元完全修饰了第一代PAMAM树枝状大分子（PAMAM G1）的外围，以高产率获得了PAMAM G1-β-CD树枝状大分子。通过氢和碳核磁共振以及质谱研究对PAMAM G1-β-CD进行了表征。此外，PAMAM G1-β-CD树枝状大分子的水溶性明显高于天然β-CD。最后，我们研究了PAMAM G1-β-CD树枝状大分子在四种不同细胞系中的毒性，即人乳腺癌细胞（MCF-7和MDA-MB-231）、人宫颈腺癌细胞（HeLa）和猪肾上皮细胞（LLC-PK1）。PAMAM G1-β-CD树枝状大分子在测试的细胞系中未表现出任何细胞毒性，这表明了这类新型树枝状大分子的潜力。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b13b/9055266/65416a877a87/d0ra02574g-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b13b/9055266/c4cbd277d5a5/d0ra02574g-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b13b/9055266/0b80cbcd8f34/d0ra02574g-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b13b/9055266/34f30c9105cf/d0ra02574g-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b13b/9055266/2b4acbf21791/d0ra02574g-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b13b/9055266/65416a877a87/d0ra02574g-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b13b/9055266/c4cbd277d5a5/d0ra02574g-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b13b/9055266/0b80cbcd8f34/d0ra02574g-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b13b/9055266/34f30c9105cf/d0ra02574g-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b13b/9055266/2b4acbf21791/d0ra02574g-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b13b/9055266/65416a877a87/d0ra02574g-f2.jpg

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