Delivery of hydrophilic compounds across membranes is usually problematic. Modification with triphenylphosphonium ions has been shown to overcome this barrier.
Lysine dendron with four triphenylphosphonium groups.
We recently included a triphenylphosphonium (TPP)-bearing dendron into our portfolio (LS-3650).
This type of building block was designed for the targeted delivery of peptides, polymers and different types of drugs to mitochondria. Bearing a hydrazide group, LS-3650 can be easily conjugated to the molecule of choice via reaction with aldehyde groups (hydrazone ligation).
Effect of the Conjugation Density of Triphenylphosphonium Cation on the Mitochondrial Targeting of Poly(amidoamine) Dendrimers; E. R. Bielski, Q. Zhong, M. Brown and S. R. P. da Rocha; Molecular pharmaceutics 2015; 12: 3043-3053. doi:10.1021/acs.molpharmaceut.5b00320
Mitochondrial targeting dendrimer allows efficient and safe gene delivery; X. Wang, N. Shao, Q. Zhang and Y. Cheng; Journal of Materials Chemistry B 2014; 2: 2546-2553. doi:10.1039/c3tb21348j
Surface conjugation of triphenylphosphonium to target poly(amidoamine) dendrimers to mitochondria; S. Biswas, N. S. Dodwadkar, A. Piroyan and V. P. Torchilin; Biomaterials 2012; 33: 4773-4782. doi:http://dx.doi.org/10.1016/j.biomaterials.2012.03.032
Multiple Triphenylphosphonium Cations as a Platform for the Delivery of a Pro-Apoptotic Peptide; N. Kolevzon, U. Kuflik, M. Shmuel, S. Benhamron, I. Ringel and E. Yavin; Pharmaceutical Research 2011; 28: 2780. doi:10.1007/s11095-011-0494-6
Multiple Triphenylphosphonium Cations Shuttle a Hydrophilic Peptide into Mitochondria; S. E. Abu-Gosh, N. Kolvazon, B. Tirosh, I. Ringel and E. Yavin; Molecular pharmaceutics 2009; 6: 1138-1144. doi:10.1021/mp900032r