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Hydrophobic tail chemistry has been implicated in these limitations; however, a systematic structure\u2013activity relationship (SAR) analysis is lacking. In this study, the authors synthesized a 56\u2010member library of tail\u2010modified ionizable lipids with biodegradable disulfide linkages and variations in chain length and branching. Systematic SAR evaluation revealed that hydrophobic tail architecture critically determines endosomal escape, biocompatibility, and mRNA translation efficiency. Optimized LNPs delivered mRNA with potent efficacy and markedly reduced cytotoxicity, lower cytokine induction, and balanced Th1\/Th2 immune activation in a nonhuman primate model. 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