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