Chem. J. Chinese Universities ›› 2018, Vol. 39 ›› Issue (12): 2707.doi: 10.7503/cjcu20180475
• Physical Chemistry • Previous Articles Next Articles
ZHAO Xiaohui1,2, CHU Zhenhua1,2, LI Yu1,2,*()
Received:
2018-07-02
Online:
2018-11-20
Published:
2018-11-20
Contact:
LI Yu
E-mail:liyuxx@jlu.edu.cn
CLC Number:
TrendMD:
ZHAO Xiaohui,CHU Zhenhua,LI Yu. Molecular Design of Lower Photodegradation Fluoroquinolone Antibiotics and Their Photolysis Paths Inference†[J]. Chem. J. Chinese Universities, 2018, 39(12): 2707.
Model | n | q2 | r2 | SEE | F | SEP | SDEPext | S | E | H | D | A | ||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
CoMFA | 6 | 0.592 | 0.998 | 0.002 | 14968.907 | 0.001 | 0.989 | 0.788 | 0.293 | 71% | 29% | - | - | - |
CoMSIA | 7 | 0.633 | 1.000 | 0.004 | 33088.010 | 0.002 | 1.000 | 0.753 | 0.312 | 48.10% | 5.70% | 31.30% | 10.80% | 4.10% |
Table 1 Statistical parameters and contributions of the molecular fields for CoMFA and CoMSIA models*
Model | n | q2 | r2 | SEE | F | SEP | SDEPext | S | E | H | D | A | ||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
CoMFA | 6 | 0.592 | 0.998 | 0.002 | 14968.907 | 0.001 | 0.989 | 0.788 | 0.293 | 71% | 29% | - | - | - |
CoMSIA | 7 | 0.633 | 1.000 | 0.004 | 33088.010 | 0.002 | 1.000 | 0.753 | 0.312 | 48.10% | 5.70% | 31.30% | 10.80% | 4.10% |
FQ | No. | Compound | Exp. | CoMFA | CoMSIA | ||
---|---|---|---|---|---|---|---|
Pred. | Relative error(%) | Pred. | Relative error(%) | ||||
Third | 1 | CIPa | 1.36 | 1.378 | 1.3 | 1.362 | 0.14 |
2 | DANb | 1.06 | 1.061 | 0.09 | 1.06 | 0 | |
3 | DIFb | 1.86 | 1.812 | -2.6 | 1.858 | -0.11 | |
4 | ENRb | 1.52 | 1.521 | 0 | 1.521 | 0 | |
5 | FLE | 0.635 | 0.752 | ||||
6 | GRE | 1.147 | 1.312 | ||||
7 | LEVb | 2.08 | 2.081 | 0 | 2.081 | 0 | |
8 | LOMa | 0.28 | 0.275 | -1.8 | 0.281 | 0.36 | |
9 | NAD | 1.076 | 1.049 | ||||
10 | NORb | 1.46 | 1.459 | -0.07 | 1.462 | 0.13 | |
11 | OFLb | 2.47 | 2.459 | -0.45 | 2.461 | -0.36 | |
12 | PEF | 1.659 | 1.622 | ||||
13 | SARb | 1.49 | 1.490 | 0 | 1.489 | -0.06 | |
14 | SPA | 0.517 | 0.515 | ||||
15 | MARb | 0.79 | 0.762 | -3.5 | 0.785 | -0.63 | |
Fourth | 16 | PAZ | 2.413 | 2.433 | |||
17 | MOX | 1.937 | 1.975 | ||||
18 | PRU | 1.849 | 1.813 | ||||
19 | RUF | 1.564 | 1.568 | ||||
20 | BALb | 2.73 | 2.730 | 0 | 2.731 | 0 | |
21 | SIT | 1.221 | 1.248 | ||||
22 | CLI | 1.255 | 1.064 | ||||
23 | OLA | 2.141 | 2.173 | ||||
24 | BES | 1.246 | 1.251 | ||||
25 | ANT | 2.162 | 2.148 | ||||
26 | GATb | 2.15 | 2.144 | 0.47 | 2.132 | 0.93 |
Table 2 lgt1/2 values of FQs predicted using the CoMFA and CoMSIA models
FQ | No. | Compound | Exp. | CoMFA | CoMSIA | ||
---|---|---|---|---|---|---|---|
Pred. | Relative error(%) | Pred. | Relative error(%) | ||||
Third | 1 | CIPa | 1.36 | 1.378 | 1.3 | 1.362 | 0.14 |
2 | DANb | 1.06 | 1.061 | 0.09 | 1.06 | 0 | |
3 | DIFb | 1.86 | 1.812 | -2.6 | 1.858 | -0.11 | |
4 | ENRb | 1.52 | 1.521 | 0 | 1.521 | 0 | |
5 | FLE | 0.635 | 0.752 | ||||
6 | GRE | 1.147 | 1.312 | ||||
7 | LEVb | 2.08 | 2.081 | 0 | 2.081 | 0 | |
8 | LOMa | 0.28 | 0.275 | -1.8 | 0.281 | 0.36 | |
9 | NAD | 1.076 | 1.049 | ||||
10 | NORb | 1.46 | 1.459 | -0.07 | 1.462 | 0.13 | |
11 | OFLb | 2.47 | 2.459 | -0.45 | 2.461 | -0.36 | |
12 | PEF | 1.659 | 1.622 | ||||
13 | SARb | 1.49 | 1.490 | 0 | 1.489 | -0.06 | |
14 | SPA | 0.517 | 0.515 | ||||
15 | MARb | 0.79 | 0.762 | -3.5 | 0.785 | -0.63 | |
Fourth | 16 | PAZ | 2.413 | 2.433 | |||
17 | MOX | 1.937 | 1.975 | ||||
18 | PRU | 1.849 | 1.813 | ||||
19 | RUF | 1.564 | 1.568 | ||||
20 | BALb | 2.73 | 2.730 | 0 | 2.731 | 0 | |
21 | SIT | 1.221 | 1.248 | ||||
22 | CLI | 1.255 | 1.064 | ||||
23 | OLA | 2.141 | 2.173 | ||||
24 | BES | 1.246 | 1.251 | ||||
25 | ANT | 2.162 | 2.148 | ||||
26 | GATb | 2.15 | 2.144 | 0.47 | 2.132 | 0.93 |
Compound | CoMFA | CoMSIA | Frequency/ cm-1 | pLOEC | ||
---|---|---|---|---|---|---|
Predicted values of lgt1/2 | Change rate(%) | Predicted values of lgt1/2 | Change rate(%) | |||
CIP | 1.36 | 1.36 | 7.58 | |||
| 1.14 | -16.2 | 1.08 | -20.6 | 65.24 | 7.69 |
| 1.11 | -18.4 | 1.14 | -16.2 | 72.37 | 7.96 |
| 0.99 | -27.2 | 1.02 | -25 | 68.54 | 8.34 |
| 1.03 | -24.3 | 1.04 | -23.5 | 77.39 | 8.07 |
| 1.08 | -20.6 | 1.03 | -24.3 | 61.02 | 8.04 |
| 1.13 | -16.9 | 1.06 | -22.1 | 63.46 | 7.78 |
| 1.29 | -5.1 | 1.22 | -10.3 | 75.21 | 8.01 |
| 1.27 | -6.6 | 1.24 | -8.8 | 70.23 | 8.19 |
| 1.25 | -8.1 | 1.14 | -16.2 | 65.30 | 8.08 |
| 1.68 | +23.5 | 1.63 | +19.9 | - | 8.32 |
Table 3 lgt1/2 predicted values, frequency and pLOEC values of the modified CIP molecules*
Compound | CoMFA | CoMSIA | Frequency/ cm-1 | pLOEC | ||
---|---|---|---|---|---|---|
Predicted values of lgt1/2 | Change rate(%) | Predicted values of lgt1/2 | Change rate(%) | |||
CIP | 1.36 | 1.36 | 7.58 | |||
| 1.14 | -16.2 | 1.08 | -20.6 | 65.24 | 7.69 |
| 1.11 | -18.4 | 1.14 | -16.2 | 72.37 | 7.96 |
| 0.99 | -27.2 | 1.02 | -25 | 68.54 | 8.34 |
| 1.03 | -24.3 | 1.04 | -23.5 | 77.39 | 8.07 |
| 1.08 | -20.6 | 1.03 | -24.3 | 61.02 | 8.04 |
| 1.13 | -16.9 | 1.06 | -22.1 | 63.46 | 7.78 |
| 1.29 | -5.1 | 1.22 | -10.3 | 75.21 | 8.01 |
| 1.27 | -6.6 | 1.24 | -8.8 | 70.23 | 8.19 |
| 1.25 | -8.1 | 1.14 | -16.2 | 65.30 | 8.08 |
| 1.68 | +23.5 | 1.63 | +19.9 | - | 8.32 |
Path | Reactant | Reaction product | Energy barrier/ (kJ·mol-1) | Enthalpies/ (kJ·mol-1) | Path | Reactant | Reaction product | Energy barrier/ (kJ·mol-1) | Enthalpies/ (kJ·mol-1) |
---|---|---|---|---|---|---|---|---|---|
1 | CIP | IM1a | 325.56 | -282.46 | IM5b | IM5c | 143.39 | -565.22 | |
IM1a | IM1b | 286.69 | -528.61 | IM5b | IM5c' | 161.92 | -504.21 | ||
IM1b | P1 | 363.55 | -560.78 | IM5c | IM5d | 227.44 | -691.24 | ||
2 | CIP | P2 | 38.83 | -423.46 | IM5d | IM5e | 372.50 | -327.23 | |
CIP | P3 | 4.69 | -508.65 | IM5e | P1 | 301.83 | -469.86 | ||
CIP | P4 | 50.88 | -374.64 | 6 | OH-CIP | IM6a | 90.29 | -385.05 | |
P4 | IM2a | 261.54 | -148.36 | IM6a | IM6b | 23.51 | -432.04 | ||
IM2a | IM2b | 315.81 | -171.59 | IM6b | P7 | 148.95 | -373.80 | ||
IM2b | P5 | 146.94 | -391.25 | 7 | OH-CIP | IM7a | 31.97 | -461.45 | |
3 | CIP | IM3a | 437.69 | -288.86 | IM7a | IM7b | 148.20 | -328.69 | |
IM3a | IM3b | 372.63 | -272.42 | IM7a | IM7c | 117.19 | -432.21 | ||
IM3b | P5 | 146.94 | -391.25 | IM7c | IM7d | 189.83 | -510.49 | ||
4 | CIP | P6 | 127.07 | -355.93 | IM7d | IM7f | 166.23 | -331.62 | |
5 | CIP | IM5a | 52.84 | -372.54 | IM7f | IM7g | 66.44 | -403.13 | |
IM5a | IM5b | 196.77 | -471.16 | IM7g | P8 | 277.69 | -302.67 |
Table 4 Energy barriers and enthalpies of possible reaction paths for CIP molecules and the modified molecules
Path | Reactant | Reaction product | Energy barrier/ (kJ·mol-1) | Enthalpies/ (kJ·mol-1) | Path | Reactant | Reaction product | Energy barrier/ (kJ·mol-1) | Enthalpies/ (kJ·mol-1) |
---|---|---|---|---|---|---|---|---|---|
1 | CIP | IM1a | 325.56 | -282.46 | IM5b | IM5c | 143.39 | -565.22 | |
IM1a | IM1b | 286.69 | -528.61 | IM5b | IM5c' | 161.92 | -504.21 | ||
IM1b | P1 | 363.55 | -560.78 | IM5c | IM5d | 227.44 | -691.24 | ||
2 | CIP | P2 | 38.83 | -423.46 | IM5d | IM5e | 372.50 | -327.23 | |
CIP | P3 | 4.69 | -508.65 | IM5e | P1 | 301.83 | -469.86 | ||
CIP | P4 | 50.88 | -374.64 | 6 | OH-CIP | IM6a | 90.29 | -385.05 | |
P4 | IM2a | 261.54 | -148.36 | IM6a | IM6b | 23.51 | -432.04 | ||
IM2a | IM2b | 315.81 | -171.59 | IM6b | P7 | 148.95 | -373.80 | ||
IM2b | P5 | 146.94 | -391.25 | 7 | OH-CIP | IM7a | 31.97 | -461.45 | |
3 | CIP | IM3a | 437.69 | -288.86 | IM7a | IM7b | 148.20 | -328.69 | |
IM3a | IM3b | 372.63 | -272.42 | IM7a | IM7c | 117.19 | -432.21 | ||
IM3b | P5 | 146.94 | -391.25 | IM7c | IM7d | 189.83 | -510.49 | ||
4 | CIP | P6 | 127.07 | -355.93 | IM7d | IM7f | 166.23 | -331.62 | |
5 | CIP | IM5a | 52.84 | -372.54 | IM7f | IM7g | 66.44 | -403.13 | |
IM5a | IM5b | 196.77 | -471.16 | IM7g | P8 | 277.69 | -302.67 |
Compound | Total score | Compound | Total score | Change rate of total score(%) | Compound | Total score | Change rate of total score(%) |
---|---|---|---|---|---|---|---|
BAL | 4.46 | CIP | 3.49 | CIP | 3.49 | ||
CIP | 3.49 | 1 | 4.36 | 24.93 | P1 | 4.48 | 28.37 |
DAN | 4.52 | 2 | 4.06 | 16.33 | P2 | 4.35 | 24.64 |
DIF | 3.59 | 3 | 4.10 | 13.99 | P3 | 3.91 | 12.03 |
ENR | 4.16 | 4 | 5.34 | 45.57 | P4 | 4.31 | 23.50 |
GAT | 4.83 | 5 | 3.69 | 4.88 | P5 | 4.41 | 26.36 |
LEV | 3.69 | 6 | 3.79 | 5.62 | P6 | 3.91 | 12.03 |
LOM | 2.81 | 7 | 4.67 | 31.98 | N1 | 4.28 | 22.64 |
NOR | 2.66 | 8 | 3.50 | 0.26 | N2 | 4.69 | 34.38 |
OFL | 3.04 | 9 | 2.94 | -11.78 | |||
SAR | 3.70 | 10 | 5.58 | 59.71 | |||
MAR | 3.67 |
Table 5 Scoring functions for docking of FQs, the modified CIP molecules and their photolysis products
Compound | Total score | Compound | Total score | Change rate of total score(%) | Compound | Total score | Change rate of total score(%) |
---|---|---|---|---|---|---|---|
BAL | 4.46 | CIP | 3.49 | CIP | 3.49 | ||
CIP | 3.49 | 1 | 4.36 | 24.93 | P1 | 4.48 | 28.37 |
DAN | 4.52 | 2 | 4.06 | 16.33 | P2 | 4.35 | 24.64 |
DIF | 3.59 | 3 | 4.10 | 13.99 | P3 | 3.91 | 12.03 |
ENR | 4.16 | 4 | 5.34 | 45.57 | P4 | 4.31 | 23.50 |
GAT | 4.83 | 5 | 3.69 | 4.88 | P5 | 4.41 | 26.36 |
LEV | 3.69 | 6 | 3.79 | 5.62 | P6 | 3.91 | 12.03 |
LOM | 2.81 | 7 | 4.67 | 31.98 | N1 | 4.28 | 22.64 |
NOR | 2.66 | 8 | 3.50 | 0.26 | N2 | 4.69 | 34.38 |
OFL | 3.04 | 9 | 2.94 | -11.78 | |||
SAR | 3.70 | 10 | 5.58 | 59.71 | |||
MAR | 3.67 |
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