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. 2022 Apr;74(2):340–372. doi: 10.1124/pharmrev.121.000445

TABLE 4.

Reported structures of adenosine receptor subtypes

PDB Engineering Ligand Resolution (Å) Technique Remarks Reference
A2AAR Antagonist Structures
3PWH TS ZM241385 (42) 3.3 X-ray (Dore et al., 2011)
3REY TS XAC (57) 3.3 X-ray (Dore et al., 2011)
3RFM TS Caffeine (3) 3.6 X-ray (Dore et al., 2011)
3UZA TS T4G (58) 3.3 X-ray T4G: 6-(2,6-dimethylpyridin-4-yl)-5-phenyl-1,2,4-triazin-3-amine (Congreve et al., 2012)
3UZC TS T4E (59) 3.3 X-ray T4E: 4-(3-amino-5-phenyl-1,2,4-triazin-6-yl)-2-chlorophenol (Congreve et al., 2012)
3EML FP (T4L) ZM241385 2.6 X-ray (Jaakola et al., 2008)
4EIY FP (bRIL) ZM241385 1.8 X-ray (Liu et al., 2012)
5UIG FP (bRIL) 8D1 (60) 3.5 X-ray 8D1: 5-amino-N-[(2-methoxyphenyl)methyl]-2-(3-methylphenyl)-2H-1,2,3-triazole-4-carboximidamide (Sun et al., 2017)
5K2A FP (bRIL) ZM241385 2.5 X-ray/SFX/XFEL, sulfur SAD phasing SFX: serial femtosecond crystallography; XFEL: X-ray free-electron laser; SAD: single-wavelength anomalous diffraction (Batyuk et al., 2016)
5K2B FP (bRIL) ZM241385 2.5 X-ray/SFX/XFEL, MR phasing MR: molecular replacement (Batyuk et al., 2016)
5K2C FP (bRIL) ZM241385 1.9 X-ray/SFX/XFEL, sulfur SAD phasing and phase extension (Batyuk et al., 2016)
5K2D FP (bRIL) ZM241385 1.9 X-ray/SFX/XFEL, MR phasing (Batyuk et al., 2016)
5VRA FP (bRIL) ZM241385 2.4 X-ray in situ in situ: film sandwich plates at room temperature (Broecker et al., 2018)
5JTB FP (bRIL) ZM241385 2.8 X-ray/I-SAD I-SAD: iodide-single-wavelength anomalous diffraction (Melnikov et al., 2017)
5UVI FP (bRIL) ZM241385 3.2 X-ray millisec millisec: serial millisecond crystallography using synchrotron radiation (Martin-Garcia et al., 2017)
6AQF FP (bRIL) ZM241385 2.5 X-ray (Eddy et al., 2018b)
7RM5 FP (bRIL) ZM241385 2.8 Microcrystal electron diffraction (Martynowycz et al., 2021)
5NM2 TS-FP (bRIL) ZM241385 2.0 X-ray millisec (cryo) (Weinert et al., 2017)
5NLX TS-FP (bRIL) ZM241385 2.1 X-ray millisec (room temp) (Weinert et al., 2017)
5NM4 TS-FP (bRIL) ZM241385 1.7 X-ray femtosec (room temp) Serial femtosecond crystallography using XFEL (Weinert et al., 2017)
5MZJ TS-FP (bRIL) Theophylline (4) 2.0 X-ray (Cheng et al., 2017)
5MZP TS-FP (bRIL) Caffeine (3) 2.1 X-ray (Cheng et al., 2017)
5N2R TS-FP (bRIL) PSB-36 (18) 2.8 X-ray (Cheng et al., 2017)
5IU4 TS-FP (bRIL) ZM241385 1.7 X-ray (Segala et al., 2016)
5IU7 TS-FP (bRIL) 12c (61, LUF6805) 1.9 X-ray 12c: 2-(furan-2-yl)-N5-(2-(4-phenylpiperidin-1-yl)ethyl)[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7-diamine (Segala et al., 2016)
5IU8 TS-FP (bRIL) 12f (62, LUF6806) 2.0 X-ray 12f: 2-(furan-2-yl)-N5-(2-(4-methylpiperazin-1-yl)ethyl)[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7-diamine (Segala et al., 2016)
5IUA TS-FP (bRIL) 12b (63, LUF6732) 2.2 X-ray 12b: 2-(furan-2-yl)-N5-(3-(4-phenylpiperazin-1-yl)propyl)[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7-diamine (Segala et al., 2016)
5IUB TS-FP (bRIL) 12x (64, LUF6632) 2.1 X-ray 12x: N5-(2-(4-(2,4-difluorophenyl)piperazin-1-yl)ethyl)-2-(furan2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7-diamine (Segala et al., 2016)
5OLG TS-FP (bRIL) ZM241385 1.9 X-ray, soaking soaking of ligand to displace theophylline in the crystals (Rucktooa et al., 2018)
5OLH TS-FP (bRIL) Vipadenant (65) 2.6 X-ray, soaking for 24 hr (Rucktooa et al., 2018)
5OLO TS-FP (bRIL) Tozadenant (66) 3.1 X-ray, soaking for 24 hr (Rucktooa et al., 2018)
5OLV TS-FP (bRIL) LUAA47070 (analog) (67/68) 2.0 X-ray, soaking for 24 hr (Rucktooa et al., 2018)
5OLZ TS-FP (bRIL) 4e (69) 1.9 X-ray 4e: 4-(3-amino-5-phenyl-1,2,4-triazin-6-yl)-2-chlorophenol (Rucktooa et al., 2018)
5OM1 TS-FP (bRIL) 4e 2.1 X-ray, soaking for 1 hr (Rucktooa et al., 2018)
5OM4 TS-FP (bRIL) 4e 2.0 X-ray, soaking for 24 hr (Rucktooa et al., 2018)
6LPJ/K/L FP (bRIL) ZM241385 1.8–2.0 Serial femtosecond crystallography using XFEL EROCOC17 + 4 as crystallization matrix (Ihara et al., 2020)
6ZDR TS-FP (bRIL) Chromone 4d (70) 1.9 X-ray (Jespers et al., 2020)
6ZDV TS-FP (bRIL) Chromone 5d (71) 2.1 X-ray (Jespers et al., 2020)
6GT3 TS-FP (bRIL) AZD4635 (22) 2.0 X-ray (Borodovsky et al., 2020)
6S0Q TS-FP (bRIL) ZM241385 2.7 Native SAD SAD: single-wavelength anomalous diffraction (Nass et al., 2020)
3VG9 antibody-stab ZM241385 2.7 X-ray (Hino et al., 2012)
3VGA antibody-stab ZM241385 3.1 X-ray (Hino et al., 2012)
A2AAR Agonist Structures
2YDO TS Adenosine (1) 3.0 X-ray (Lebon et al., 2011)
2YDV TS NECA (6) 2.6 X-ray (Lebon et al., 2011)
4UG2 TS CGS21680 (10) 2.6 X-ray (Lebon et al., 2015)
4UHR TS CGS21680 2.6 X-ray (Lebon et al., 2015)
3QAK FP (T4L) UK432097 (11) 2.7 X-ray WT receptor (Xu et al., 2011)
5WF5 FP (bRIL) UK432097 2.6 X-ray D52N mutant (White et al., 2018)
5WF6 FP (bRIL) UK432097 2.9 X-ray S91A mutant (White et al., 2018)
5G53 truncated and tagged WT NECA (6) 3.4 X-ray with engineered G protein (mini-Gs) (Carpenter et al., 2016)
6GDG FP (thioredoxin) NECA 4.1 cryo-EM with engineered G protein (mini-Gs-β1γ2); also includes nanobody Nb35 (Garcia-Nafria et al., 2018)
7ARO TS-FP (bRIL) LUF5833 (56) 3.1 X-ray LUF5833 is a partial agonist (Amelia et al., 2021)
A1AR Antagonist Structures
5N2S TS PSB-36 (18) 3.3 X-ray (Cheng et al., 2017)
5UEN FP (bRIL) DU172 (72) 3.2 X-ray (Glukhova et al., 2017)
A1AR Agonist Structures
6D9H tagged WT receptor Adenosine (1) 3.6 cryo-EM with engineered Gi2 protein (Draper-Joyce et al., 2018)
7LD3/4 tagged WT receptor Adenosine (1) +/− MIPS521 (73) 3.3–3.4 cryo-EM with engineered Gi2 protein (Draper-Joyce et al., 2021)

FP, fusion protein; PDB, Protein Data Bank four-digit entry number; TS, thermostabilization.

Chemical structures of ligands are depicted in Fig. 3, if not already in Figs. 1 and 2.