Lucente-Schultz Rebecca M, Moore Valerie C, Leonard Ashley D, Price B Katherine, Kosynkin Dmitry V, Lu Meng, Partha Ranga, Conyers Jodie L, Tour James M
Department of Chemistry and Mechanical Engineering, The Smalley Institute for Nanoscale Science and Technology, Rice University, MS-222, 6100 Main Street, Houston, Texas 77005, USA.
J Am Chem Soc. 2009 Mar 25;131(11):3934-41. doi: 10.1021/ja805721p.
Single-walled carbon nanotubes (SWCNTs) and ultrashort SWCNTs (US-SWCNTs) were functionalized with derivatives of the phenolic antioxidant, butylated hydroxytoluene (BHT). By using the oxygen radical absorbance capacity (ORAC) assay, the oxygen radical scavenging ability of the SWCNT antioxidants is nearly 40 times greater than that of the radioprotective dendritic fullerene, DF-1. In addition, ORAC results revealed two divergent trends in the antioxidant potential of SWCNTs, depending on the type of functionalization employed. When existing pendant sites on US-SWCNTs were further functionalized by either covalent or noncovalent interactions of the existing pendant sites with a BHT derivative, the amount of BHT-derivative loading proportionately increased the overall antioxidant activity. If, however, functionalization occurred via covalent functionalization of a BHT-derivative directly to the SWCNT sidewall, the amount of BHT-derivative loading was inversely proportional to the overall antioxidant activity. Therefore, increasing the number of pendant sites on the SWCNT sidewalls by covalent functionalization led to a concomitant reduction in ORAC activity, suggesting that the nanotube itself is a better radical scavenger than the BHT-derivatized SWCNT. Cytotoxicity assays showed that both nonfunctionalized and BHT-derivatized SWCNTs have little or no deleterious effect on cell viability. Therefore, SWCNTs may be attractive agents for antioxidant materials and medical therapeutics research.
单壁碳纳米管(SWCNTs)和超短单壁碳纳米管(US-SWCNTs)用酚类抗氧化剂丁基化羟基甲苯(BHT)的衍生物进行了功能化处理。通过使用氧自由基吸收能力(ORAC)测定法,SWCNT抗氧化剂的氧自由基清除能力比辐射防护树枝状富勒烯DF-1的清除能力大近40倍。此外,ORAC结果揭示了SWCNTs抗氧化潜力的两种不同趋势,这取决于所采用的功能化类型。当US-SWCNTs上现有的悬垂位点通过现有悬垂位点与BHT衍生物的共价或非共价相互作用进一步功能化时,BHT衍生物的负载量相应增加了总体抗氧化活性。然而,如果功能化是通过将BHT衍生物直接共价功能化到SWCNT侧壁上发生的,BHT衍生物的负载量与总体抗氧化活性成反比。因此,通过共价功能化增加SWCNT侧壁上的悬垂位点数量会导致ORAC活性随之降低,这表明纳米管本身比BHT衍生化的SWCNT是更好的自由基清除剂。细胞毒性测定表明,未功能化和BHT衍生化的SWCNTs对细胞活力几乎没有或没有有害影响。因此,SWCNTs可能是抗氧化材料和医学治疗研究中有吸引力的试剂。