Molecular structure, aromaticity, vibrational investigation and dual descriptor for chemical reactivity on 1- chloroisoquinoline using quantum chemical studies

Vidhya, V.; Austine, A.; Arivazhagan, M.

doi:10.1016/j.rinma.2020.100097

Cited by 11 publications

(4 citation statements)

References 38 publications

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“…According to Koopmans's theorem, the transfer of electrons takes place from the HOMO energy (E HOMO ) level to the LUMO energy (E LUMO ) level, which is represented by ionisation potential and electron affinity, respectively [27][28][29]. Amongst the phlorotannins, PtB demonstrated a significant E HOMO value (ionisation potential) of −4.513 eV and an E LUMO value (electron affinity) of −0.810 eV, indicating its easy electron donating and electron accepting capabilities when compared to volasertib, which showed the higher values of E HOMO (−5.192 eV) and E LUMO (−0.970 eV), respectively [30]. Furthermore, hardness indices measure the stability of molecules, whereas softness indexes show molecular reactivity.…”

Section: Evaluation and Analysis Of Chemical Descriptormentioning

confidence: 99%

Pentafuhalol-B, a Phlorotannin from Brown Algae, Strongly Inhibits the PLK-1 Overexpression in Cancer Cells as Revealed by Computational Analysis

Ansari,

Rab,

Saquib

et al. 2023

Molecules

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Polo-like kinase-1 (PLK-1) is an essential mitotic serine/threonine (Ser/Thr) kinase that belongs to the Polo-like kinase (PLK) family and is overexpressed in non-small cell lung cancer (NSCLC) via promotion of cell division. Therefore, PLK-1 may act as a promising target for the therapeutic cure of various cancers. Although a variety of anti-cancer drugs, both synthetic and naturally occurring, such as volasertib, onvansertib, thymoquinone, and quercetin, are available either alone or in combination with other therapies, they have limited efficacy, especially in the advanced stages of cancer. To the best of our knowledge, no anticancer agent has been reported from marine algae or microorganisms to date. Thus, the aim of the present study is a high-throughput virtual screening of phlorotannins, obtained from edible brown algae, using molecular docking and molecular dynamic simulation analysis. Among these, Pentafuhalol-B (PtB) showed the lowest binding energy (best of triplicate runs) against the target protein PLK-1 as compared to the reference drug volasertib. Further, in MD simulation (best of triplicate runs), the PtB-PLK-1 complex displayed stability in an implicit water system through the formation of strong molecular interactions. Additionally, MMGBSA calculation (best of triplicate runs) was also performed to validate the PtB-PLK-1 complex binding affinities and stability. Moreover, the chemical reactivity of PtB towards the PLK-1 target was also optimised using density functional theory (DFT) calculations, which exhibited a lower HOMO-LUMO energy gap. Overall, these studies suggest that PtB binds strongly within the pocket sites of PLK-1 through the formation of a stable complex, and also shows higher chemical reactivity than the reference drug volasertib. The present study demonstrated the inhibitory nature of PtB against the PLK-1 protein, establishing its potential usefulness as a small molecule inhibitor for the treatment of different types of cancer.

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Section: Evaluation and Analysis Of Chemical Descriptormentioning

confidence: 99%

Pentafuhalol-B, a Phlorotannin from Brown Algae, Strongly Inhibits the PLK-1 Overexpression in Cancer Cells as Revealed by Computational Analysis

Ansari,

Rab,

Saquib

et al. 2023

Molecules

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show abstract

“…The dual descriptor: − normalΔ f ( r ) = ( δ 3 E δ v false( r false) ∂ 2 N ) = true( ∂ f ( r ) ∂ N true) v ( r ) = true( δ η δ v ( r ) true) N …”

Section: Theoretical Backgroundunclassified

1,3 Dipolar Cycloaddition of Münchnones: Factors behind the Regioselectivity

et al. 2023

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The 1,3 dipolar cycloaddition reactions of münchnones and alkenes provide an expedite synthetic way to substituted pyrroles, an exceedingly important structural motif in the pharmaceutical and material science fields of research. The factors governing their regioselectivity rationalization are not well understood. Using several approaches, we investigate a set of 14 reactions (featuring two münchnones, 12 different alkenes, and two alkynes). The Natural Bond Theory and the Non-Covalent Interaction Index analyses of the noncovalent interaction energies fail to predict the experimental major regioisomer. Employing global cDFT descriptors or local ones such as the Fukui function and dual descriptor yields similarly inaccurate predictions. Only the local softness pairing, within Pearson’s Hard and Soft Acids and Bases principle, constitutes a reliable predictor for the major reaction product. By taking into account an estimator for the steric effects, the correct regioisomer is predicted. Steric effects play a major role in driving the regioselectivity, as was corroborated by energy decomposition analysis of the transition states.

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“…It is manifest and obvious that the evaluation of standard deviation (S.D) and scale factors provide fine agreement between the experimental and the calculated fundamental modes of vibrations. The RMS deviation and correlation coefficient for observed and calculated wave numbers at B3LYP/6-31þþG (d,p) level have been carried out using the following equation [32,33].…”

Section: Error Analysis Of Different Fundamentalsmentioning

confidence: 99%

Experimental approach, theoretical investigation and molecular docking of 2- chloro-5-fluoro phenol antibacterial compound

Vidhya

Austine

Arivazhagan

2020

Heliyon

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Molecular structure, aromaticity, vibrational investigation and dual descriptor for chemical reactivity on 1- chloroisoquinoline using quantum chemical studies

Cited by 11 publications

References 38 publications

Pentafuhalol-B, a Phlorotannin from Brown Algae, Strongly Inhibits the PLK-1 Overexpression in Cancer Cells as Revealed by Computational Analysis

Pentafuhalol-B, a Phlorotannin from Brown Algae, Strongly Inhibits the PLK-1 Overexpression in Cancer Cells as Revealed by Computational Analysis

1,3 Dipolar Cycloaddition of Münchnones: Factors behind the Regioselectivity

Experimental approach, theoretical investigation and molecular docking of 2- chloro-5-fluoro phenol antibacterial compound

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