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. Author manuscript; available in PMC: 2014 Jan 1.
Published in final edited form as: Bioorg Med Chem Lett. 2012 Nov 5;23(1):26–36. doi: 10.1016/j.bmcl.2012.10.112

Table 1.

Structures of fluorescent adenosine receptor (AR) ligands. In this table, the conjugates are structurally divided into three moieties to fulfill pharmacological, covalent linking, and fluorescent functions (see Figure 1 for structures of fluorophores and Table 2 for references).

No. Compound Namea Pharmacophore Linker Fluorophore
1 FITC-ADAC graphic file with name nihms425538t1.jpg - FITC
2 NBD-ADAC NBD
3 FITC-APEC graphic file with name nihms425538t2.jpg - FITC
4 Alexa488-
APEC (salt form)		 Alexa Fluor 488
5/6 mixed isomers
5 MRS5424 Alexa Fluor 532
6 Dansyl-NECA
(n=3)		 graphic file with name nihms425538t3.jpg (CH2)3NH Dansyl
7 Dansyl-NECA
(n=4)b 		(CH2)4NH
8 Dansyl-NECA
(n=6)		 (CH2)6NH
9 Dansyl-NECA
(n=8)		 (CH2)8NH
10 Dansyl-NECA
(n=10)		 (CH2)10NH
11 Dansyl-NECA
(n=12)		 (CH2)12NH
12 ABEA-AO-dansyl
(8)		 (CH2)4NHCO(CH2)7NH
13 AUEA-dansyl (10) (CH2)11NH
14 NBD-NECA (n=2) (CH2)2NH NBD
15 NBD-NECA (n=4) (CH2)4NH
16 NBD-NECA (n=6) (CH2)6NH
17 NBD-NECA (n=8) (CH2)8NH
18 NBD-NECA (n=10) (CH2)10NH
19 APrEA-X-BY630 (CH2)3NH Bodipy 630/650-X
20 ABEA-X-BY630 (CH2)4NH
21 APEA-X-BY630 (CH2)5NH
22 AOEA-X-BY630 (CH2)8NH
23 ADOEA-X-BY630 ((CH2)2O)2(CH2)2NH
24 NECA-Bodipy-
630/650 (n=2)		 (CH2)2NH Bodipy-630/650
25 NECA-Bodipy-
630/650 (n=3)		 (CH2)3NH
26 NECA-Bodipy-
630/650 (n=4)		 (CH2)4NH
27 NECA-Bodipy-
630/650 (n=8)		 (CH2)8NH
28 NECA-Bodipy-
630/650 (n=11)		 (CH2)11NH
29 NECA-Bodipy-
630/650 (PEG n=2)		 CH2(CH2OCH2)2CH2NH
30 NECA-Bodipy-
630/650 (PEG n=3)		 CH2(CH2OCH2)3CH2NH
31 ABEA-BYLF (CH2)4NH Bodipy FL
32 ABEA-X-BYLF (CH2)4NHCO(CH2)5NH
33 ABEA-X-Texas
Red		 (CH2)4NH Texas Red
34 ABEA-Cy5 Cy5
35 ABEA-EVOBlue30 EVOBlue 30
36 ABA-X-BY630 graphic file with name nihms425538t4.jpg (CH2)4NH Bodipy 630/650-X
37 FITC-XAC graphic file with name nihms425538t5.jpg - FITC
38 FITC-Gly3-XAC CONHCH2
39 XAC-X-BY630 - Bodipy 630/650-X
40 XAC-X-Texas Red - Texas Red
41 XAC-Cy5 Cy5
42 XAC-AEAO-BYFL CO(CH2)6CONH(CH2)2NH Bodipy FL
43 XAC-EVOBlue30 - EVOBlue 30
44 XAC-Dansyl Dansyl
45 XAC-AO-Dansyl CO(CH2)7NH
46 XAC-AHH-Dansyl CO(CH2)5NHCO(CH2)5NH
47 TQO-C8-X-
BODIPY630		 graphic file with name nihms425538t6.jpg CO(CH2)2CONH(CH2)8NH Bodipy 630/650-X
48 TQO-PEG-X-
BODIPY630		 CO(CH2)2CONH((CH2)2O)2(CH2)2NH
49 TQO-PEG-X-
BODIPY-TR		 Bodipy-TR
50 TQO-PEG-Cy5 Cy5
51 TQO-PEG-TAMRA Tamra 5/6-X
mixed isomers
52 TQO-extPEG-
TAMRA		 5-Tamra-PEG
53 MRS5346 graphic file with name nihms425538t7.jpg CH2CONH(CH2)2NH Alexa Fluor 488
5-isomer
54 MRS5418 CH2CONH((CH2)2NH)2 Bodipy650/665-X
55 MRS5347 CH2CONH(CH2)2 Tamra
56 MRS5449 graphic file with name nihms425538t8.jpg CO(CH2)3 Alexa Fluor 488
azide 5-isomer
57 PTP-FITC (1) graphic file with name nihms425538t9.jpg NH FITC
58 PTP-FITC (2) (CH2)3NH
59 PTP-FITC (3) (CH2)4NH
60 PTP-FITC (4) (CH2)5NH
61 PTP-FITC (5) ((CH2)2O)2(CH2)2NH
62 PTP-FITC (6) (CH2)3O((CH2)2O)2(CH2)3NH
63 MRS5218 graphic file with name nihms425538t10.jpg C≡C(CH2)2CONH(CH2)2NH Cy5
64 MRS5243 C≡C(CH2)4 Squaraine-
Rotaxane
65 MRS5238 C≡C(CH2)4 Alexa Fluor 488
azide
66 MRS5704 C≡C 4-Pyrene
67 MRS5783 C≡C 1-Pyrene
68 MRS5421 graphic file with name nihms425538t11.jpg
69 MRS5422
70 MRS5397 graphic file with name nihms425538t12.jpg
71 MRS5399 graphic file with name nihms425538t13.jpg
72 MRS5303 graphic file with name nihms425538t14.jpg
a

abbreviations: ABA: N6-(aminobutyl)adenosine; ABEA: N6-(4-aminobutyl)-5′-ethylamino-5′-oxo-5′-deoxyadenosine; ADAC: adenosine amine congener; ADOEA: N6-(8-amino-3,6-dioxaoctyl)-5′-ethylamino-5′-oxo-5′-deoxyadenosine; AEAO: 8-(2-aminoethylamino)-8-oxooctanoyl; AHH: 6-(6-aminohexanamido)hexanoyl; AO: 8-aminooctanoyl; AOEA: N6-(8-aminooctyl)-5′-ethylamino-5′-oxo-5′-deoxyadenosine; APEA: N6-(5-aminopentyl)-5′-ethylamino-5′-oxo-5′-deoxyadenosine; APrEA: N6-(3-aminopropyl)-5′-ethylamino-5′-oxo-5′-deoxyadenosine; APEC: 2-[(2-aminoethylamino)carbonylethyl-phenylethylamino]-5′-ethylcarboxamidoadenosine; AUEA: N6-(11-aminoundecyl)-5′-ethylamino-5′-oxo-5′-deoxyadenosine; CGS15943: 9-chloro-2-(2-furanyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine; (N)-methanocarba: [3.1.0]bicyclohexane; NECA: 5'-N-ethylcarboxamidoadenosine; PAMAM: polyamidoamine; PTP: pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine; QD: quantum dot; SCH442416: 2-(2-furanyl)-7-[3-(4-methoxyphenyl)propyl]-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine; TQO: [1,2,4]-triazolo[4,3-a]quinoxalin-1-one; TQZ: [1,2,4]-triazolo[1,5-c]quinazolin-5-amine; XAC: xanthine amine congener.

b

structure is same as ABEA-dansyl.36