Correlation study of antibacterial activity and spectrum of Penicillins through a structure-activity relationship analysis

Morán-Díaz, Jessica R; Jiménez‐Vázquez, Hugo A.; Gómez-Pliego, Raquel; Arellano-Mendoza, Mónica Griselda; Quintana, Delia; Guevara‐Salazar, Juan Alberto

doi:10.1007/s00044-019-02391-9

Cited by 11 publications

(8 citation statements)

References 110 publications

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“…3 D and Dataset S3 ). In particular, the gene clusters coding for biosyntheses of antimicrobial substances present high similarity scores [e.g., showdomycin ( 38 ), promysalin ( 39 ), curacomycin ( 40 ), neopolyoxin C ( 41 ), and thienamycin ( 42 )]. Physiological assays further support these observations, and find that the Pseudonocardiaceae strains exclusively have negative effects on the growth of gram-positive bacteria, such as Bacillus subtilis ( Fig.…”

Section: Resultsmentioning

confidence: 99%

Multikingdom interactions govern the microbiome in subterranean cultural heritage sites

Liu

Zhou

Jin

et al. 2022

Proc. Natl. Acad. Sci. U.S.A.

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Significance The conservation of historical relics against microbial biodeterioration is critical to preserving cultural heritages. One major challenge is our limited understanding of microorganisms’ dispersal, colonization, and persistence on relics after excavation and opening to external environments. Here, we investigate the ecological and physiological profiles of the microbiome within and outside the Dahuting Han Dynasty Tomb with a 1,800-y history. Actinobacteria dominate the microbiome in this tomb. Via interkingdom signaling mutualism, springtails carry Actinobacteria as one possible source into the tomb from surrounding environments. Subsequently, Actinobacteria produce cellulases combined with antimicrobial substances, which helps them to colonize and thrive in the tomb via intrakingdom competition. Our findings unravel the ecology of the microbiomes colonizing historical relics and provide help for conservation practices.

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Section: Resultsmentioning

confidence: 99%

Multikingdom interactions govern the microbiome in subterranean cultural heritage sites

Liu

Zhou

Jin

et al. 2022

Proc. Natl. Acad. Sci. U.S.A.

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“…Penicillins, especially penicillin G, are among the first line of antimicrobial agents currently in use for the treatment of intra-hospital infections [2]. However penicillins suffer from inactivity against Gram negative bacteria [1].…”

Section: Discussionmentioning

confidence: 99%

“…Beta-lactam antibiotics inhibit the synthesis of bacterial cell membranes, while they activate the autolytic enzymes which destroy cell membranes, simultaneously [1]. Nowadays, penicillins constitute about 50% of the antimicrobial agents currently in use (WHO 2018a, 2018b) [2] and they are first choice drugs in the treatment of nosocomial infections [2]. Benzyl-penicillin (penicillin G) is the gold standard penicillin, which is obtained biotechnologically using the fungus P. chrysogenum [1].…”

Section: Introductionmentioning

confidence: 99%

Conjugation of Penicillin-G with Silver(I) Ions Expands Its Antimicrobial Activity against Gram Negative Bacteria

et al. 2020

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Conjugation of penicillin G (PenH) with silver(I) ions forms a new CoMeD (conjugate of metal with a drug) with formula [Ag(pen)(CH3OH)]2 (PenAg). PenAg was characterized by a plethora of physical and spectroscopic techniques, which include in the solid state m.p.; elemental analysis; X-ray fluorescence (XRF) spectroscopy; scanning electron microscopy (SEM); energy-dispersive X-ray spectroscopy (EDX); FT-IR; and in solution: attenuated total reflection spectroscopy (FT-IR-ATR), UV–Vis, 1H NMR, and atomic absorption (AA). The structure of PenAg was determined by NMR spectroscopy. Silver(I) ions coordinate to the carboxylic group of PenH, while secondary intra-molecular interactions are developed through (i) the nitrogen atom of the amide group in MeOD-d4 or (ii) the sulfur atom in the thietane ring in deuterated dimethyl sulfoxide DMSO-d6. The antibacterial activities of PenAg and the sodium salt of penicillin (PenNa) (the formulation which is clinically used) against Gram positive (Staphylococcus epidermidis (S. epidermidis) and Staphylococcus aureus (S. aureus)) and Gram negative (Pseudomonas aeruginosa (P. aeuroginosa PAO1)) bacteria were evaluated by the means of minimum inhibitory concentration (MIC), minimum bactericidal concentration (MBC), and inhibition zone (IZ). PenAg inhibits the growth of the Gram negative bacterial strain P. aeuroginosa with a MIC value of 23.00 ± 2.29 μM, in contrast to PenNa, which shows no such activity (>2 mM). The corresponding antimicrobial activities of PenAg against the Gram positive bacteria S. epidermidis and S. aureus are even better than those of PenNa. Moreover, PenAg exhibits no in vivo toxicity against Artemia salina at concentration up to 300 μΜ. The wide therapeutic window and the low toxicity, make PenAg a possible candidate for the development of a new antibiotic.

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“…The QSAR was performed under QSAR-2D, proposed by Corwin Hansch and Toshio Fujita [49,50]. Concerning the physicochemical properties of the N-arylbenzylimines, size was measured by molar refractivity (Advanced Chemistry Development, Inc.) and lipophilicity by the partition coefficient [51,52]. These parameters were determined on ACD/ChemSketch 2015 and CS ChemDraw Pro v.6 software, respectively [53].…”

Section: Qsar Studymentioning

confidence: 99%

Physicochemical Interpretation, with QSAR/SAR Analysis, of How the Barriers Of Pseudomonas Aeruginosa Bacteria Were Penetrated by Para-Substituted N-Arylbenzylimines: Synthesis, Characterization, and In Vitro Antibacterial Effect

et al. 2021

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Abstract. Resistance to antibiotics is a growing problem that imposes limitations on current therapy around the world. The World Health Organization (WHO) recommends creating new antibacterial molecules to inhibit the most harmful bacteria by aiming at specific targets. Among such bacteria is multi-drug resistant Pseudomonas aeruginosa, a Gram-negative bacterium responsible for 70% of invasive infections worldwide. The aim of this investigation was to synthesize N-arylbenzylimines, examine their antibacterial activity against P. aeruginosa ATCC 27853, and determine their physicochemical properties by quantitative structure-activity relationship (QSAR/SAR) analysis. Seven N-arylbenzylimines were synthesized with yields ≥50%, all with the E-configuration (as shown by NMR spectra and confirmed with X-ray diffraction). The in vitro microbiological evaluations were carried out with the Kirby-Bauer method, following the guidelines of the Clinical & Laboratory Standards Institute (CLSI). The N-arylbenzylimines produced a very good antibacterial effect on P. aeruginosa, with minimum inhibitory concentration (MIC) values ranging from 198.47-790.10 µM, calculated by the Hill method. Based on the slopes of the concentration-response curves, the mechanism of action is different between the test compounds and aztreonam, the reference drug. The QSAR study performed with in vitro experimental data found that biological activity correlates most significantly with molecular size, followed by lipophilicity and electronic effects. According to the SAR analysis of antibacterial activity, molecules cross bacterial barriers differently if they bear substituents with resonance versus inductive electronic effects. The physicochemical data presently described are of utmost importance for designing and developing new molecules to combat the pathogenicity and resistance of P. aeruginosa. Resumen. La resistencia a los antibióticos es un problema en aumento que impone limitaciones en la terapia actual a nivel mundial. La Organización Mundial de la Salud (OMS) recomienda crear nuevas moléculas antibacterianas para inhibir las bacterias más dañinas por medio de dianas específicas. Pseudomonas aeruginosa, entre estas bacterias, es Gram-negativa, resistente a múltiples fármacos, y responsable del 70% de las infeccione invasivas en el mundo. El objetivo de esta investigación fue sintetizar N-arilbenziliminas, examinar su actividad antibacteriana contra P. aeruginosa ATCC 27853, y determinar sus propiedades fisicoquímicas mediante análisis cuantitativo de relación estructura-actividad (QSAR/SAR). Todos los siete N-arilbenziliminas sintetizados tuvieron rendimientos ≥50% y la configuración E (de acuerdo con la espectroscopía de RMN y la difracción de rayos-X). Las pruebas microbiológicas in vitro se realizaron mediante el método Kirby-Bauer, siguiendo las directrices del Instituto de Estándares Clínicos y de Laboratorio (CLSI). Las N-arilbenziliminas mostraron efecto antibacteriano relevante sobre P. aeruginosa, con valores de la concentración mínima inhibitoria (MIC) en el rango de 198.47-790.10 µM, calculado por el método de Hill. Las pendientes de las curvas de concentración-respuesta sugieren que el mecanismo de acción es distinto entre las N-arilbenziliminas y aztreonam, el fármaco de referencia. El analisis QSAR de los datos experimentales indica que la actividad biológica se correlaciona de manera más significativa con el tamaño molecular, seguida de la lipofilicidad y los efectos electrónicos. Según el análisis SAR de la actividad antibacteriana, las moléculas cruzan las barreras bacterianas en forma diferente si portan sustituyentes con efectos electrónicos inductivos versus de resonancia. Estos datos fisicoquímicos son de suma importancia en el diseño y desarrollo de nuevas moléculas para combatir la infección y resistencia de P. aeruginosa.

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Correlation study of antibacterial activity and spectrum of Penicillins through a structure-activity relationship analysis

Cited by 11 publications

References 110 publications

Multikingdom interactions govern the microbiome in subterranean cultural heritage sites

Multikingdom interactions govern the microbiome in subterranean cultural heritage sites

Conjugation of Penicillin-G with Silver(I) Ions Expands Its Antimicrobial Activity against Gram Negative Bacteria

Physicochemical Interpretation, with QSAR/SAR Analysis, of How the Barriers Of Pseudomonas Aeruginosa Bacteria Were Penetrated by Para-Substituted N-Arylbenzylimines: Synthesis, Characterization, and In Vitro Antibacterial Effect

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