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1H NMR Spectra of Resorufin Arachidonate. TMS. CHCl3. EtOAc impurities. EtOAc impurities. N. O. O. O. O. 1H NMR (CDCl3,360 MHz). DCM impurity. EtOAc.

SUPPORTING INFORMATION Synthesis and Evaluation of Cytosolic Phospholipase A 2 Activatable Fluorophores for Cancer Imaging Michael G. Chiorazzo†,‡, Noah B. Bloch‡, Anatoliy V. Popov‡, and Edward J. Delikatny‡ † Department of Pharmacology, University of Pennsylvania, Philadelphia, PA 19104, USA ‡ Department of Radiology, University of Pennsylvania, Philadelphia, PA 19104, USA

Table of Contents: Figure S1…………………………………………………………………………………S2 Figure S2………………………………………………………………………………....S3 Figure S3…………………………………………………………………………………S4 Figure S4…………………………………………………………………………………S5 Figure S5…………………………………………………………………………………S6

S1

8.5 7.5 7.0 6.5 5.5

H NMR (CDCl3, 360 MHz)

N O

4.5 4.0 f1 (ppm)

Figure S1. H NMR Spectra of Resorufin Arachidonate 1

S2 3.0 2.0

3.53

1

6.08

6.85 1.58 0.95 1.92 1.24 1.66 1.54

8.35

0.65

0.72 1.05 0.75 0.69

0.75

DCM impurity EtOAc impurities

CHCl3 EtOAc impurities

O

O

O

EtOAc impurities TMS

1.0 0.0

0.90 0.89 0.86

2.83 2.64 2.62 2.60 2.39 2.37 2.35 2.25 2.24 2.22 2.20 2.17 2.15 2.13 2.11 1.90 1.88 1.86 1.84 1.82 1.77 1.75 1.73 1.71 1.68 1.30

5.38

7.45 7.42 7.26 7.15 7.14 7.13 7.11 6.33 6.33

7.81 7.78

1.26

0.90 0.88 0.86

1.81 1.79 1.77 1.75 1.73

2.62 2.60 2.58

7.81 7.78

7.45 7.42 7.26 7.15 7.14 7.13 7.11 6.33 6.33

DCM impurity

CHCl3

1

H NMR (CDCl3, 360 MHz) O

N

O

O O

7.5

8.5

7.0

6.5

5.5

4.5 4.0 3.5 f1 (ppm)

1

Figure S2. H NMR Spectra of Resorufin Palmitate

S3

2.5

1.5

3.82

23.95

2.28

2.00

0.87

1.02 0.90 0.98 0.93

1.02

TMS

0.5

-0.5

8.5 7.5 7.0 6.5 5.5 4.5 4.0 3.5 f1 (ppm)

Figure S3. H NMR Spectra of DDAO Arachidonate 1

S4 2.5 1.5

3.62

8.42

2.15 2.32 6.35

Cl

2.08

CHCl3 N

5.99

8.19

1.00 1.04

0.99 0.89

1

H NMR (CDCl3, 360 MHz)

O O

Cl

O

TMS

0.5 -0.5

0.88 0.87 0.85

2.22 2.20 2.18 2.04 2.02 1.86 1.27

2.81 2.61 2.59 2.57

5.37

7.66 7.63 7.62 7.24 7.21 7.21 7.12 7.12 7.10 7.09

1.86 1.79 1.77 1.75 1.73 1.24 1.01 0.88 0.86 0.84

2.59 2.57 2.55

3.58

7.66 7.63 7.62 7.24 7.22 7.21 7.12 7.12 7.10 7.09

1

H NMR (CDCl3 : MeOH, 20 : 1, 360 MHz) Cl O

N

CHCl3

Cl

O

O

MeOH impurities

TMS MeOH impurities

7.5

8.5

7.0

6.5

5.5

4.5 4.0 3.5 f1 (ppm)

1

Figure S4. H NMR Spectra of DDAO Palmitate

S5

2.5

1.5

3.61

24.05

6.35 2.45

2.18

1.00 1.08

1.03 0.86

DCM impurity

0.5

-0.5

0.79 0.77 0.75

1.60 1.58 1.56 1.19

2.22 2.20 2.18 1.97

2.69

5.25

7.97

7.55 7.27 7.23 7.21 7.20 7.05 7.04 6.61 6.59

8.52 8.50

EtOAc impurities TMS

1

H NMR (CDCl3, 360 MHz) EtOAc impurities

O O

O O O

O O

7.5

8.5

7.0

6.5

5.5

4.5 4.0 3.5 f1 (ppm)

1

Figure S5. H NMR Spectra of Naphthofluorescein Diarachidonate

S6

2.5

1.5

6.73

12.15

4.04

7.75

3.75

12.70

16.00

1.69

EtOAc impurities

3.04 2.18

1.61

0.71

1.51

CHCl3

0.5

-0.5