Development of QSARs to investigate the bacterial toxicity and biotransformation potential of aromatic heterocylic compounds

Bundy, Jacob G.; Morriss, Alistair; Durham, David G.; Campbell, Colin D.; Paton, Graeme I.

doi:10.1016/s0045-6535(00)00178-8

Cited by 48 publications

(33 citation statements)

References 28 publications

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“…Total biodegradation (TB d ) is another useful and important factors in chemical and biochemical studies [33]. The LC 50 value is called the median lethal concentration and lethal concentration 50, this value gives an idea of the relative acute toxicity of an in halable material.…”

Section: Discussionmentioning

confidence: 99%

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Chemical compositions of the essential oil and calculation the biophysicochemical coefficients of the components of Hymenocrater longiflorus Benth. of Iran

Maroofi¹,

Changizi²,

Shoushtari³

et al. 2011

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The volatile constituents of the essential oil of Hymenocrater longiflorus Benth. growing wild in Kurdistan-Iran were investigated using the GC and GC/MS techniques. Fifteen compounds, representing twenty (97.03%) of the total oil were identified. The main components were: α-Pinene (22.47%), β-Caryophyllene (18.05%), β-Eudesmol (14.92%), α-Copaene (9.84%), γ-Elemene (6.79%), δ-Cadine-ne (6.13%), (-)Bornyl acetate (5.61%), α-Amorphene (3.84%), α-Fenchyl acetate (2.35%) and β-Pinene (2.07%). Some of the physicochemical properties like the logarithm of calculated Octanol-Water partitioning coefficients (log K ow ) , total biodegradation and (TB d in mol/h and gr./h), water solubility (S w , mg.L -1 at 25ºC) and median lethal concentration 50 (LC 50 ) were calculated for the 15 components of Hymenocrater longiflorus Benth.

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Section: Discussionmentioning

confidence: 99%

“…The log K ow is used in models to estimate plant and soil invertebrate bioaccumulation factors. This parameter is also used in many environmental studies to help determine the environmental fate of chemicals [3][4][5].…”

Section: Introductionmentioning

confidence: 99%

Chemical compositions of the essential oil and calculation the biophysicochemical coefficients of the components of Hymenocrater longiflorus Benth. of Iran

Maroofi¹,

Changizi²,

Shoushtari³

et al. 2011

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“…Heterocyclic aromatic compounds are highly ubiquitous in the environment and are known to exhibit diverse ecotoxic effects such as acute toxicity, developmental and reproductive toxicity, cytotoxicity, photo-induced toxicity, mutagenicity, and carcinogenicity (Bundy et al 2001;Barron et al 2004;Robbiano et al 2004;Brack et al 2007;Eisentraeger et al 2008).…”

Section: Toxicitymentioning

confidence: 99%

Properties, environmental fate and biodegradation of carbazole

2017

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The last two decades had witnessed extensive investigation on bacterial degradation of carbazole, an Nheterocyclic aromatic hydrocarbon. Specifically, previous studies have reported the primary importance of angular dioxygenation, a novel type of oxygenation reaction, which facilitates mineralization of carbazole to intermediates of the TCA cycle. Proteobacteria and Actinobacteria are the predominant bacterial phyla implicated in this novel mode of dioxygenation, while anthranilic acid and catechol are the signature metabolites. Several studies have elucidated the degradative genes involved, the diversity of the car gene clusters and the unique organization of the car gene clusters in marine carbazole degraders. However, there is paucity of information regarding the environmental fate as well as industrial and medical importance of carbazole and its derivatives. In this review, attempt is made to harness this information to present a comprehensive outlook that not only focuses on carbazole biodegradation pathways, but also on its environmental fate as well as medical and industrial importance of carbazole and its derivatives.

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“…Parameters like dipole moment, LUMO energy, hardness and electrophilicity were considered to predict model, since these parameters are widely used to describe the stability, toxicity and reactivity of the chemical compounds (Kapur et al, 2000). We also considered the hydrophobicity, as many authors reported the quantitative correlation of toxicity, activity and metabolism of the compounds with the octanol-water distribution coefficient descriptor (Bundy et al, 2001, Ren and Frymier, 2002, Worgan et al, 2003. In order to establish a better predictability, PLS based QSAR study was performed by considering experimentally observed values (pIC 50 ), along with various descriptors, are presented in Tables 1.…”

Section: Qsar Models For Inhibitor Activitymentioning

confidence: 99%

In silico ADME/T and 3D QSAR analysis of KDR inhibitors

Hosen¹,

Dash²,

Khatun³

et al. 2017

J App Pharm Sci

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Tyrosine kinases (KDR) have been considered as a potential targets for the design of new anticancer agents. Recently, a series of N-4-chlorophenylnaphthamides has been reported with KDR inhibitory activity. In order to demonstrate the pharmacokinetics and the relationship between the structures and their inhibition of KDR, 3D-QSAR and in silico ADME/T analysis were performed on a dataset of 13 compounds. Quantum chemical parameters such as LUMO energy, HOMO energy, ionization energy (I), electron affinity (A), chemical potential (μ), hardness (η) and electrophilicity (χ) of the compounds are calculated by using semi-empirical SCF-MO method at PM3 level of theory and various SlogP descriptors from MOE software. In silico ADME/T analysis was performed by using different software's Discovery Studio 2.5, TOPKAT and QikProp 4.3. From in silico ADME and Toxicity studies, it was revealed that selected derivatives have good oral absorption rate and metabolism with no BBB penetration. QSTR (Quantitative Structure Toxicity Relationship) studies by using TOPAK in various computational animal models, showed high LD50 values and the compounds are found to be noncarcenogenic. Moreover, three different QSAR models were generated by Partial Least Squares (PLS) Regression method having correlation coefficient (Q 2 ) of 0.86382, 0.84372, and 0.82629, respectively. These models conclude a significant relationship of KDR inhibition with dipole moment (D), LUMO energy (ELUMO), hardness (η) and electrophilicity (χ), and hydrophobicity of compounds, regarding N-4-chlorophenylnaphthamides.

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Development of QSARs to investigate the bacterial toxicity and biotransformation potential of aromatic heterocylic compounds

Cited by 48 publications

References 28 publications

Chemical compositions of the essential oil and calculation the biophysicochemical coefficients of the components of Hymenocrater longiflorus Benth. of Iran

Chemical compositions of the essential oil and calculation the biophysicochemical coefficients of the components of Hymenocrater longiflorus Benth. of Iran

Properties, environmental fate and biodegradation of carbazole

In silico ADME/T and 3D QSAR analysis of KDR inhibitors

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