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Departamento De Química - Física DEPARTAMENTO DE QUÍMICA - FÍSICA SELECCIÓN DE NUEVOS ANTIBACTERIANOS POR TOPOLOGÍA MOLECULAR VICTORIA EUGENIA SIMÓN GARCÍA UNIVERSITAT DE VALENCIA Servei de Publicacions 2004 Aquesta Tesi Doctoral va ser presentada a Valencia el día 04 de Desembre de 2003 davant un tribunal format per: - D. José Luis Moreno Frigols - Dª. Mª Teresa Salabert Salvador - D. Enrique Hernández Jiménez - Dª. Stella Moreno Grau - Dª. Marina Herraez Domínguez Va ser dirigida per: D. Facundo Pérez Giménez D. Francisco José García March ©Copyright: Servei de Publicacions Victoria Eugenia Simón García Depòsit legal: I.S.B.N.:84-370-5170-3 Edita: Universitat de València Servei de Publicacions C/ Artes Gráficas, 13 bajo 46010 València Spain Telèfon: 963864115 UNIVERSITAT DE VALÈNCIA FACULTAT DE FARMÀCIA DEPARTAMENT DE QUÍMICA FÍSICA "SELECCIÓN DE NUEVOS ANTIBACTERIANOS POR TOPOLOGÍA MOLECULAR" Memoria para optar al Grado de Doctora en Farmacia, presentada por: VICTORIA EUGENIA SIMÓN GARCÍA Directores: Prof. Dr. D. FACUNDO PÉREZ GIMÉNEZ Prof. Dr. D. FRANCISCO JOSÉ GARCÍA MARCH 1 2 DPTO. QUÍMICA FÍSICA FACULTAD DE FARMACIA Av. Vicente Andrés Estellés s/n Tf. 963 86 48 94 Fax 963 86 48 92 46100 BURJASSOT (Valencia) ESPAÑA D. FACUNDO PÉREZ GIMÉNEZ y D. FRANCISCO JOSÉ GARCÍA MARCH, Doctores en Farmacia y Profesores Titular y Asociado del Departamento de Química Física de la Facultad de Farmacia de la Universidad de Valencia, CERTIFICAN: Que la Tesis Doctoral presentada sobre el tema “Selección de nuevos antibacterianos por topología molecular” ha sido realizada bajo nuestra dirección por la Licenciada en Farmacia Dña. VICTORIA EUGENIA SIMÓN GARCÍA y mediante este escrito, autorizan su presentación para optar al grado de Doctora en Farmacia. Burjassot, 14 de Julio de 2003. Fdo.: Facundo Pérez Giménez Fdo.: Francisco José García March 3 4 "SELECCIÓN DE NUEVOS ANTIBACTERIANOS POR TOPOLOGÍA MOLECULAR" 5 6 Quisiera expresar mi más sincero y profundo agradecimiento a mis directores, Dr. D. Facundo Pérez Giménez y Dr. D. Francisco José García March quienes han prestado mucho más que su colaboración para la realización del presente trabajo, su tiempo, su dedicación, sus conocimientos, su experiencia, su paciencia, aportando además estímulo, apoyo y amistad. Sin el conjunto de todo ello no habría sido posible la realización de la presente Tesis Doctoral. Mención muy especial al Dr. D. Miguel Murcia Soler, al que quiero agradecer su desinteresada colaboración, su consejo, su tiempo y su apoyo en todo momento. Su ayuda ha sido realmente inestimable. A la Dra. Dña. María Teresa Salabert Salvador, quien siempre me ha mostrado su interés, su estímulo y ayuda. A Ana Pérez Solsona, por su colaboración en la realización de los ensayos farmacológicos. A todos los compañeros del Servicio de Análisis Clínicos del Hospital General de Castellón por el ánimo y el interés mostrado, así como por haber compartido conmigo muchos momentos buenos y algunos que no lo fueron tanto.. A todos los que en algún momento me ayudaron y apoyaron. A TODOS. Gracias por hacer que sea así. Gracias a los que me disteis sin pedir nada a cambio. Gracias a los que pedisteis algo, sin duda me considerabais una amiga. Gracias a los que en alguna ocasión me hicisteis llorar, de nuevo fui una niña. Gracias a los que reísteis conmigo, sin duda fuimos felices. 7 8 Gracias a los que hablasteis de mí en algún momento, bien o mal, poco o mucho, entonces me hicisteis presente. Gracias a los que nunca me echasteis nada en cara, a pesar de mi carácter. Gracias a los que alguna vez me echasteis algo en cara, me hicisteis ver mi imperfección. A mis padres, Juan y Victoria. Todo lo que soy se lo debo a ellos. Se esforzaron en mi educación y bienestar. Me han dado lo que jamás ellos tuvieron. Ojalá todos los padres fueran como vosotros. A mi hermano, Juan, excelente hermano mayor, mejor persona, del que hay que aprender y tomar ejemplo. A mi marido, Javi, por su aliento, su estímulo, a veces su compresión y paciencia, siempre su fuerza y su amor. A mi hijo, Ángel. Eres el mayor de mis éxitos. 9 10 A Ángel. 11 12 ÍNDICE ÍNDICE 13 14 ÍNDICE 1. INTRODUCCIÓN ........................................................................ 25 1.1. CONCEPTO DE ANTIMICROBIANO...................................................27 1.2. ANTECEDENTES HISTÓRICOS DE LOS ANTIMICROBIANOS ...28 2. ANTECEDENTES BIBLIOGRÁFICOS ..................................33 2.1. CONECTIVIDAD MOLECULAR .........................................................36 2.1.1. Origen de la conectividad molecular .................................................36 2.1.1.1. Significado de la estructura molecular ........................................36 2.1.1.2. El aspecto topológico .....................................................................40 2.1.2. Resultados obtenidos por la topología molecular.............................42 2.1.3. Elementos de la teoría de los grafos.................................................45 2.1.4. La matriz topológica .........................................................................47 2.1.5. Descripción del formato Smiles........................................................49 2.1.6. Índices topológicos.............................................................................51 2.1.6.1. Índice de Wiener............................................................................52 2.1.6.2. Índice de Randic ............................................................................53 2.1.7. Descripción del método de conectividad molecular .......................55 2.1.8. Índices de conectividad de Kier y Hall............................................59 - Índice de orden cero (0χ) ..................................................................60 - Índice de primer orden (1χ)..............................................................61 - Índice de segundo orden (2χ)............................................................61 - Índice de tercer orden (3χ) ...............................................................62 - Índice de cuarto orden (4χ)...............................................................63 - Índices de orden superior ................................................................64 - Índices de valencia............................................................................64 - Índices topológicos............................................................................68 15 16 ÍNDICE - Índices electrotopológicos ................................................................71 - Índices tipo de átomo de estado electrotopológico.........................73 - Índices tipo de enlace de estado electrotopológico.........................75 - Índices ortogonales: los índices de diferencia chi ..........................77 2.2. FLUORQUINOLONAS: REVISIÓN BIBLIOGRÁFICA ...................80 2.2.1. Antecedentes históricos.....................................................................80 2.2.2. Estructura química............................................................................82 2.2.3. Relación estructura-actividad ..........................................................84 2.2.4. Mecanismo de acción.........................................................................85 2.2.5. Actividad antibacteriana ..................................................................91 2.2.6. Selectividad ........................................................................................93 2.2.7. Resistencias ........................................................................................93 2.2.8. Farmacocinética................................................................................95 2.2.8.1. Absorción........................................................................................95 2.2.8.2. Distribución...................................................................................96 2.2.8.3. Eliminación.....................................................................................97 2.2.9. Actividad farmacológica...................................................................98 2.2.10. Aplicaciones terapéuticas.................................................................99 3. MATERIAL Y MÉTODOS ........................................................103 3.1. DISEÑO Y SELECCIÓN MOLECULAR .............................................105 3.1.1. Selección del grupo farmacológico a investigar..............................105 3.1.2. Obtención de las funciones topológicas ...........................................106 3.1.2.1. Búsqueda bibliográfica de las propiedades ................................106 17 18 ÍNDICE 3.1.2.2. Obtención de grafos a partir del formato Smiles y cálculo de los índices topológicos ..........................................................................106 3.1.2.3. Obtención de las funciones de conectividad................................107 3.1.3. Obtención de las funciones discriminantes .....................................108 3.1.3.1. Análisis lineal discriminante.........................................................108 3.1.3.2. Patrones de actividad farmacológica ...........................................111 3.2. TRATAMIENTO INFORMÁTICO.......................................................113 3.2.1. Obtención de los índices de conectividad ........................................113 3.2.1.1. Descripción del programa Molconn-Z........................................113 3.2.2. Obtención de las funciones de conectividad y análisis lineal discriminante .....................................................................................116
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