Table 1.

Summary of NMR interaction studies between porphyrins and biomolecules.

Porphyrin (Guest)	Macromolecule (Host)	NMR Technique	Result	Ref
Phospholipids
Ce6 Ce6 derivatives	DOPC-SUVs	1H NMR chem. shift perturbation of host Time-dependent 1H NMR chem. shift perturbation of host	Ce6 attached to PL-bilayer head group Transmembrane kinetics of Ce6 (flip-flop) pH dependence of kinetics	[131,133]
Ce6, Ce6 derivatives PPIX, DPIX, HPIX and derivatives	DOPC-SUVs	1H NMR chem. shift perturbation of host	Porphyrin aggregate structure determines membrane interaction	[84]
Ce6 derivatives PPIX, DPIX, HPIX and derivatives TPP derivatives	DOPC-SUVs	1H NMR chem. shift perturbation of host Time-dependent 1H NMR chem. shift perturbation of host	Different patterns of bilayer localization and transmembrane kinetics depending on porphyrin structure and substitution Patterns used for classification of membrane interactions	[134]
TPP Zn-TPP	DMPC liposomes	1H NMR spectral appearance of guest	Transfer from CD complex to liposome	[138]
TPP	Egg-PC liposomes	1H NMR chem. shift perturbation of host	Liposomal localization (hydrophobic core)	[139]
Proteins
Ce6	Bovine rhodopsin 19F-/15N-Trp-labeled rhodopsin	1H-, 19F- and 15N-NMR chem. shift perturbation of host 1H-15N NMR HSQC 1H NMR spectral appearance of guest	Weak binding of Ce6 to rhodopsin localized at cytoplasmic domain	[142]
Ce6 SerCe	HSA Tf	1H NMR spectral appearance of guest	Binding to both HSA and Tf PVP encapsulation prevents binding BCM encapsulation prevents only Tf binding	[143]
Nucleic acids
TMPyP, Ni(II)TMPyP, Zn(II)TMPyP	DNA	31P NMR chem. shift perturbation of host	TMPyP, Ni(II)TMPyP intercalate, Zn(II)TMPyP binds to the outside of DNA	[147]
Cationic TMPyP derivatives	DNA	31P-, 1H NMR chem. shift perturbation of host	Review: Three binding modes (intercalation, outside binding, outside binding with self-stacking)	[148]