BTTAA,a (Cu(I)) ligand stabilizer and catalyst,can enhances bioorthogonal click reactions and reduces cytotoxicity by lowering the amount of copper ions used. BTTAA can be used with azide to label and detect azide-labeled complexes in Jurkat cells, zebrafish, and bacteria [1.3].
Experimental proof that 50 μM BTTAA-Cu(I) complex have no effect on cell viability[2]. BTTAA-Cu(I) catalyst provided the strongest labeling of the SiaNAz-displaying cells, yielding cell-associated Alexa Fluor 488 signal 3 to 4-fold higher than the signal achieved[3] .Cu-BTTAA performs significantly better as a catalyst than Cu-THPTA or Cu-TBTA. BTTAA has been shown to perform much better than THPTA or TBTA [4.5].
References:
[1] Haldón E, Nicasio MC, Pérez PJ. Copper-catalysed azide-alkyne cycloadditions (CuAAC): an update. Org Biomol Chem. 2015 Oct 7;13(37):9528-50.
[2] Yang M, Yang Y, Chen PR. Transition-Metal-Catalyzed Bioorthogonal Cycloaddition Reactions. Top Curr Chem (Cham). 2016 Feb;374(1):2.
[3]Besanceney-Webler C, Jiang H, Zheng T, Feng L, Soriano del Amo D, Wang W, Klivansky LM, Marlow FL, Liu Y, Wu P. Increasing the efficacy of bioorthogonal click reactions for bioconjugation: a comparative study. Angew Chem Int Ed Engl. 2011 Aug 22;50(35):8051-6.
[4] Besanceney-Webler C, Jiang H, Zheng T, Feng L, Soriano del Amo D, Wang W, Klivansky LM, Marlow FL, Liu Y, Wu P. Increasing the efficacy of bioorthogonal click reactions for bioconjugation: a comparative study. Angew Chem Int Ed Engl. 2011 Aug 22;50(35):8051-6.
[5] Loh CT, Ozawa K, Tuck KL, Barlow N, Huber T, Otting G, Graham B. Lanthanide tags for site-specific ligation to an unnatural amino acid and generation of pseudocontact shifts in proteins. Bioconjug Chem. 2013 Feb 20;24(2):260-8.
BTTAA 一种 (Cu(I)) 配体稳定剂和催化剂，可提高生物正交点击反应，并降低铜离子用量，减少细胞毒性。BTTAA可与叠氮化物一起使用，用于标记和检测 Jurkat 细胞、斑马鱼和细菌中的叠氮化物标记的复合物[1. 3]。
实验证明50 μM BTTAA-Cu(I) 复合物不影响细胞活力[2]。BTTAA-Cu(I) 催化剂对 SiaNAz-displaying细胞的标记效果强，产生的细胞相关 Alexa Fluor 488 信号比实际信号高出 3 至 4 倍[3]。Cu-BTTAA 作为催化剂的性能明显优于 Cu-THPTA 或 Cu-TBTA，BTTAA 的性能远优于 THPTA或 TBTA[4.5]。