Synthesis and Biological Evaluation of 2,5-Bis(alkylamino)-1,4-benzoquinones
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis of 2,5-diamino-p-benzoquinones
2.2. Phytotoxic activity
Compound | Cucumis sativus | Sorghum bicolor | ||||||
---|---|---|---|---|---|---|---|---|
24 h | 48 h | 24 h | 48 h | |||||
Radiclelength [cm]a | Inhibition [%] | Radiclelength [cm]a | Inhibition [%] | Radiclelenght [cm]a | Inhibition [%] | Radiclelength [cm]a | Inhibition [%] | |
12 | 1.40 def | 42 | 1.94 fg | 59 | 0.87 cd | 36 | 1.04 fg | 30 |
13 | 1.75 cde | 28 | 3.91 bcd | 18 | 1.90 ab | -40 | 3.50 abc | -135 |
14 | 2.17 abc | 10 | 4.87 a | -2 | 1.69 ab | -24 | 3.70 ab | -148 |
15 | 2.02 abc | 17 | 3.43 de | 28 | 1.14 bcd | 17 | 1.87 defg | -26 |
16 | 2.02 abc | 17 | 4.24 abcd | 11 | 1.52 abc | -12 | 1.91 defg | -28 |
17 | 1.89 bcd | 22 | 2.73 ef | 43 | 1.17 bcd | 14 | 2.25 bcdef | -51 |
18 | 1.25 ef | 48 | 1.25 g | 74 | 0.49 d | 64 | 0.51 g | 66 |
19 | 2.26 abc | 7 | 3.73 ef | 22 | 1.81 ab | -33 | 3.81 a | -156 |
20 | 1.85 cd | 24 | 2.33 f | 51 | 1.23 bcd | 10 | 2.07 cdef | -39 |
21 | 2.46 a | -2 | 4.41 abc | 7 | 2.09 a | -54 | 3.21 abcd | -115 |
22 | 1.16 f | 52 | 1.79 fg | 62 | 0.85 cd | 38 | 0.92 fg | 38 |
23 | 2.10 abc | 13 | 4.41 abc | 7 | 1.47 abc | -8 | 2.82 abcde | -89 |
Control | 2.42 ab | 4.76 ab | 1.36 abc | 1.49 efg |
Compound | Ipomoea grandifolia | Brachiaria decumbens | ||||||
---|---|---|---|---|---|---|---|---|
24 h | 48 h | 24 h | 48 h | |||||
Radiclelength [cm]a | Inhibition [%] | Radiclelength [cm]a | Inhibition [%] | Radiclelenght [cm]a | Inhibition [%] | Radiclelength [cm]a | Inhibition [%] | |
12 | 0.91 de | 48 | 0.91 d | 67 | 0.87 cd | 47 | 1.06 bcd | 43 |
13 | 1.19 cd | 32 | 2.47 ab | 10 | 1.82 a | -11 | 2.90 a | -56 |
14 | 1.41 abc | 20 | 2.74 a | 0 | 1.69 ab | -3 | 3.07 a | -65 |
15 | 1.43 abc | 19 | 2.39 ab | 13 | 1.48 abc | 10 | 2.35 ab | -26 |
16 | 1.48 abc | 16 | 2.41 ab | 12 | 1.10 bcd | 33 | 1.50 bcd | 19 |
17 | 1.23 cd | 30 | 1.49 bcd | 46 | 1.59 abc | 3 | 2.21 ab | -19 |
18 | 0.94 de | 47 | 0.94 d | 66 | 0.45 d | 73 | 0.45 d | 76 |
19 | 1.69 ab | 4 | 2.25 abc | 18 | 1.67 ab | -2 | 2.98 a | -60 |
20 | 1.22 cd | 31 | 1.57 bcd | 43 | 1.51 abc | 8 | 1.93 abc | -4 |
21 | 1.32 bcd | 26 | 2.40 ab | 12 | 1.80 ab | -10 | 2.82 a | -51 |
22 | 0.77 e | 56 | 1.35 cd | 51 | 0.65 d | 60 | 0.86 cd | 54 |
23 | 1.35 bc | 23 | 2.72 a | 1 | 1.73 ab | -5 | 3.02 a | -62 |
Control | 1.76 a | 2.72 a | 1.64 ab | 1.86 abc |
2.3. ATP assay
2.4. Anti-tumor activity
Compound | Cellsa IC50b [µg/mL]; Confident interval | |||||
---|---|---|---|---|---|---|
HL-60 | SF-295 | HCT-8 | MDA-MB-435 | PBMC | ||
12 | 2.3(1.3-3.9) | 6.0 (4.6-7.9) | 5.2(2.4-11.2) | 5.6(3.8-8.4) | >25 | |
13 | >25 | >25 | >25 | >25 | Nd | |
14 | >25 | >25 | >25 | >25 | Nd | |
16 | >25 | >25 | >25 | >25 | Nd | |
17 | >25 | >25 | >25 | >25 | Nd | |
18 | >25 | >25 | >25 | >25 | Nd | |
19 | >25 | >25 | >25 | >25 | Nd | |
20 | 20.3(17.6-23.4) | 11.3(8.6-14.9) | 13.5(9.1-20.1) | 21.5(18.7-24.8) | 21,8 (15,6-30,1) | |
21 | >25 | >25 | >25 | >25 | Nd | |
22 | >25 | >25 | >25 | >25 | Nd | |
23 | >25 | >25 | >25 | >25 | Nd | |
Doxorrubicin | 0.02(0.01-0.02) | 0.23(0.19-0.25) | 0.01(0.01-0.02) | 0.48(0.34-0.66) | 0,96 (0,51-1,71) |
3. Experimental
3.1. General
3.2. Synthesis of compounds 12-16, 18-23, exemplified by the synthesis of 2,5-bis(isopentylamino)-1,4-benzoquinone (17)
3.3. Biological assays
3.3.1. Phytotoxic activity
3.3.2. Assay of radicle elongation on Petri dishes
3.3.3. Measurement of the ATP synthesis
3.4. Cytotoxicity screening
3.4.1. Cell lines and cell cultures
3.4.2. MTT assay
3.4.3. Alamar Blue assay
4. Conclusions
Acknowledgements
- Sample Availability: Contact the authors.
References and notes
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Almeida Barbosa, L.C.; Alves Pereira, U.; Alvares Maltha, C.R.; Ricardo Teixeira, R.; Moreira Valente, V.M.; Oliveira Ferreira, J.R.; Costa-Lotufo, L.V.; Odorico Moraes, M.; Pessoa, C. Synthesis and Biological Evaluation of 2,5-Bis(alkylamino)-1,4-benzoquinones. Molecules 2010, 15, 5629-5643. https://doi.org/10.3390/molecules15085629
Almeida Barbosa LC, Alves Pereira U, Alvares Maltha CR, Ricardo Teixeira R, Moreira Valente VM, Oliveira Ferreira JR, Costa-Lotufo LV, Odorico Moraes M, Pessoa C. Synthesis and Biological Evaluation of 2,5-Bis(alkylamino)-1,4-benzoquinones. Molecules. 2010; 15(8):5629-5643. https://doi.org/10.3390/molecules15085629
Chicago/Turabian StyleAlmeida Barbosa, Luiz Cláudio, Ulisses Alves Pereira, Célia Regina Alvares Maltha, Róbson Ricardo Teixeira, Vânia Maria Moreira Valente, José Roberto Oliveira Ferreira, Letícia Veras Costa-Lotufo, Manoel Odorico Moraes, and Cláudia Pessoa. 2010. "Synthesis and Biological Evaluation of 2,5-Bis(alkylamino)-1,4-benzoquinones" Molecules 15, no. 8: 5629-5643. https://doi.org/10.3390/molecules15085629