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. 2019 Oct 1;1(11):4207–4237. doi: 10.1039/c9na00308h

Example anionic counterions used in hydrophobic ion pairing.

Name Structure MW, Da pKa log P Used to pair with
1-Hydroxy-2-naphthoic acid (xinafoic acid) graphic file with name c9na00308h-u1.jpg 188.2 3.02 2.6 AZD2811 (ref. 38 and 89)
2-Naphthalene sulfonic acid (NSA) graphic file with name c9na00308h-u2.jpg 208.2 −1.8 2.14 Atazanavir28
Brilliant blue FCF graphic file with name c9na00308h-u3.jpg 792.8 5.83 and 6.58 −1.45 Atenolol155
Carboxy methyl polyethylene glycol (CM-PEG) graphic file with name c9na00308h-u4.jpg PEG length not given Bovine serum albumin56
Lysozyme56
r-met-HuGdNF56
Cholesteryl hemisuccinate graphic file with name c9na00308h-u5.jpg 486.7 5.8 8.5 Colistin156
Doxorubicin112
Cholic acid (sodium cholate) graphic file with name c9na00308h-u6.jpg 408.6 4.98 2.02 AZD2811 (ref. 38 and 89)
Bovine serum albumin56
Lysozyme56
r-met-HuGdNF56
Insulin157
Decanoic acid (sodium decanoate/sodium caprate) graphic file with name c9na00308h-u7.jpg 194.3 4.9 4.09 Octreotide9,96
Dimyristoyl phosphatidyl glycerol (DMPG) graphic file with name c9na00308h-u8.jpg 666.9 1.89 9.2 Insulin42
Salmon calcitonin85
Dioleoyl phosphatidic acid (DOPA) graphic file with name c9na00308h-u9.jpg 701 1.3 13.2 Doxorubicin71
Gefitinib30
Docosahexaenoic acid graphic file with name c9na00308h-u10.jpg 328.5 4.89 6.75 Doxorubicin70
Hexadecylphosphate graphic file with name c9na00308h-u11.jpg 320.4 6.38 Doxorubicin158
Thymopentin159
Tobramycin160
Linoleic acid graphic file with name c9na00308h-u12.jpg 280.5 4.77 6.8 Vancomycin64
N,N-Dipalmitoyl-l-lysine graphic file with name c9na00308h-u13.jpg Colistin156
Oleic acid (sodium oleate also used) graphic file with name c9na00308h-u14.jpg 282.5 5 6.78 AZD2811 (ref. 38 and 89)
Berberine161
Desmopressin77,86
Dorzolamide81
Doxorubicin106,121
Insulin86,102,162
Leuprolide86,94,101
Lumefantrine48
Lycobetaine163
Lysozyme57,58
Octreotide96
OZ439 (ref. 43 and 154)
Polymyxin B78
Salmon calcitonin85
Vincristine164
Pamoic acid (disodium pamoate also used) graphic file with name c9na00308h-u15.jpg 388.4 2.68 6.17 AZD2811 (ref. 38)
Bovine serum albumin165
Cinnarizine47
Clozapine47
Donepezil166
Insulin165
Leuprolide165
Polymyxin B78
Sodium acetate graphic file with name c9na00308h-u16.jpg 82 4.7 −0.2 Doxorubicin61
Propanolol61
Quinidine sulfate61
Verapamil61
Sodium cholesteryl sulfate graphic file with name c9na00308h-u17.jpg 466.3 3.13 4.2 Colistin156
Sodium decanesulfonate (SDES) graphic file with name c9na00308h-u18.jpg 244.3 3.75 Doxorubicin116
Sodium deoxycholate graphic file with name c9na00308h-u19.jpg 392.6 4.65 3.8 AZD2811 (ref. 38)
Bovine serum albumin165
Ciprofloxacin88
Insulin80,93,165
Lanreotide98
Leuprolide165
Mitoxantrone diHCl79
Octreotide9,96
Papain97
Salmon calcitonin85
Sodium docusate (AOT, sodium dioctyl sulfosuccinic acid, sodium bis-2- ethylhexyl-sulfosuccinate) graphic file with name c9na00308h-u20.jpg 444.6 −0.75 5.2 α-Chymotrypsin167
Atazanavir28
AZD2811 (ref. 38 and 89)
Bevacizumab168
Bovine serum albumin56,169
Cisplatin83
Concanavalin A167
Desmopressin45,77,86,170
Doxorubicin116
Gentamycin82,117–119,171
Irinotecan29
Lanreotide98
Leuprolide45,84,86,110,172
Lysozyme56
Minocycline173
Mtb8.4 (ref. 174)
Naloxone117
Naltrexone117
Octreotide9
r-met-HuGdNF56
Tobramycin175
Trypsin167
Vancomycin176
Sodium dodecyl benzenesulfonate (SDBS) graphic file with name c9na00308h-u21.jpg 348.5 −1.7 3.73 Polymyxin B78
Sodium dodecyl sulfate (sodium lauryl sulfate) graphic file with name c9na00308h-u22.jpg 288.4 −1.5 1.6 Bovine serum albumin56
Desmopressin77,86
Dorzolamide81
IGG-Fab fragment90
Insulin49,58,84,86,111,177,178
Irinotecan29
Leuprolide11,84,86
Lysozyme18,56,57
Melittin109
Octreotide92,96
Polymyxin B78
r-met-HuGdNF56
Sodium laurate (sodium dodecanoate) graphic file with name c9na00308h-u23.jpg 222.3 4.95 5.3 Bovine serum albumin165
Insulin165
Leuprolide165
Sodium n-octadecyl sulfate (sodium stearyl sulfate) graphic file with name c9na00308h-u24.jpg 372.5 6.8 Desmopressin77
Lanreotide98
Sodium stearate (stearic acid also used) graphic file with name c9na00308h-u25.jpg 306.5 4.7 8.23 Desmopressin77
Doxorubicin61
Propanolol61
Quinidine sulfate61
Verapamil61
Sodium stearoyl glutamate (SSG) graphic file with name c9na00308h-u26.jpg 435.6 6.3 Bovine serum albumin165
Insulin165
Leuprolide165
Sodium taurodeoxycholate (STDC) graphic file with name c9na00308h-u27.jpg 499.7 −0.94 4.5 Doxorubicin72,95,116
Idarubicin95
Sodium tetradecyl sulfate graphic file with name c9na00308h-u28.jpg 316.4 −1.1 5.04 Doxorubicin95
Idarubicin95
Sodium tripolyphosphate graphic file with name c9na00308h-u29.jpg 367.9 0.89 −1.9 Irinotecan29
Taurocholic acid (sodium taurocholate also used) graphic file with name c9na00308h-u30.jpg 515.7 1.4 0.79 Bovine serum albumin56
Lanreotide98
Lysozyme56
r-met-HuGdNF56
IGG-Fab fragment90
Vitamin E (α-tocopherol) succinate graphic file with name c9na00308h-u31.jpg 530.8 4 10.2 Doxorubicin105