BIOMAT Database Logo BIOMAT Database Logo

Heterocyclic analogs of DNA minor groove alkylating agents. 1998

P G Baraldi, and B Cacciari, and A Guiotto, and R Romagnoli, and A N Zaid, and G Spalluto
Dipartimento di Scienze Farmaceutiche, Università di Ferrara, Italy. pgb@ifeuniv.unife.it

It is generally accepted that neoplastic transformation is related to genes alteration or oncogene activation. In particular, DNA minor groove binding drugs have been extensively studied through the years in order to influence the regulation of gene expression by means of specific interactions with DNA bases moieties. Pyrrolo[2,1-c],[1,4].benzodiazepines (PBDs), CC-1065 and distamycins are three classes of minor groove binders which showed interesting cytotoxicity profiles, refined through already reviewed processes of SAR studies. Among the modifications to the three families of antitumor compounds, heterocyclic substitutions have been extensively applied by many groups in order to either modify the reactivity profile or introduce extra interactions within the minor groove, thus changing the binding site or modulating the binding sequence. The updated material related to these modifications has been rationalised and ordered to offer an overview of the argument.

UI MeSH Term Description Entries
D002626 Chemistry, Pharmaceutical Chemistry dealing with the composition and preparation of agents having PHARMACOLOGIC ACTIONS or diagnostic use. Medicinal Chemistry,Chemistry, Pharmaceutic,Pharmaceutic Chemistry,Pharmaceutical Chemistry,Chemistry, Medicinal
D006575 Heterocyclic Compounds, 3-Ring A class of heterocyclic compounds that include a three-ring fused structure. Both aromatic or non-aromatic ring structures are included in this category. Fused Heterocyclic Compounds, Three-Ring,Heterocyclic Cpds, 3 Ring,Three Ring Heterocyclic Compounds,3-Ring Heterocyclic Compounds,Fused Heterocyclic Compounds, Three Ring,Heterocyclic Compounds, 3 Ring
D000477 Alkylating Agents Highly reactive chemicals that introduce alkyl radicals into biologically active molecules and thereby prevent their proper functioning. Many are used as antineoplastic agents, but most are very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. They have also been used as components in poison gases. Alkylating Agent,Alkylator,Alkylators,Agent, Alkylating,Agents, Alkylating
D000876 Anthramycin A broad-spectrum spectrum antineoplastic antibiotic isolated from Streptomyces refuineus var. thermotolerans. It has low toxicity, some activity against Trichomonas and Endamoeba, and inhibits RNA and DNA synthesis. It binds irreversibly to DNA. Anthramycin, (11a alpha)-Isomer,Antramycin
D000970 Antineoplastic Agents Substances that inhibit or prevent the proliferation of NEOPLASMS. Anticancer Agent,Antineoplastic,Antineoplastic Agent,Antineoplastic Drug,Antitumor Agent,Antitumor Drug,Cancer Chemotherapy Agent,Cancer Chemotherapy Drug,Anticancer Agents,Antineoplastic Drugs,Antineoplastics,Antitumor Agents,Antitumor Drugs,Cancer Chemotherapy Agents,Cancer Chemotherapy Drugs,Chemotherapeutic Anticancer Agents,Chemotherapeutic Anticancer Drug,Agent, Anticancer,Agent, Antineoplastic,Agent, Antitumor,Agent, Cancer Chemotherapy,Agents, Anticancer,Agents, Antineoplastic,Agents, Antitumor,Agents, Cancer Chemotherapy,Agents, Chemotherapeutic Anticancer,Chemotherapy Agent, Cancer,Chemotherapy Agents, Cancer,Chemotherapy Drug, Cancer,Chemotherapy Drugs, Cancer,Drug, Antineoplastic,Drug, Antitumor,Drug, Cancer Chemotherapy,Drug, Chemotherapeutic Anticancer,Drugs, Antineoplastic,Drugs, Antitumor,Drugs, Cancer Chemotherapy
D001665 Binding Sites The parts of a macromolecule that directly participate in its specific combination with another molecule. Combining Site,Binding Site,Combining Sites,Site, Binding,Site, Combining,Sites, Binding,Sites, Combining
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D015195 Drug Design The molecular designing of drugs for specific purposes (such as DNA-binding, enzyme inhibition, anti-cancer efficacy, etc.) based on knowledge of molecular properties such as activity of functional groups, molecular geometry, and electronic structure, and also on information cataloged on analogous molecules. Drug design is generally computer-assisted molecular modeling and does not include PHARMACOKINETICS, dosage analysis, or drug administration analysis. Computer-Aided Drug Design,Computerized Drug Design,Drug Modeling,Pharmaceutical Design,Computer Aided Drug Design,Computer-Aided Drug Designs,Computerized Drug Designs,Design, Pharmaceutical,Drug Design, Computer-Aided,Drug Design, Computerized,Drug Designs,Drug Modelings,Pharmaceutical Designs
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D018736 DNA Adducts The products of chemical reactions that result in the addition of extraneous chemical groups to DNA. DNA Adduct,Adduct, DNA,Adducts, DNA

Related Publications

P G Baraldi, and B Cacciari, and A Guiotto, and R Romagnoli, and A N Zaid, and G Spalluto
DNA minor groove alkylating agents.
April 2001, Current medicinal chemistry,
P G Baraldi, and B Cacciari, and A Guiotto, and R Romagnoli, and A N Zaid, and G Spalluto
Distamycin A as stem of DNA minor groove alkylating agents.
January 2004, Current topics in medicinal chemistry,
P G Baraldi, and B Cacciari, and A Guiotto, and R Romagnoli, and A N Zaid, and G Spalluto
Synthesis and characterization of DNA minor groove binding alkylating agents.
January 2013, Chemical research in toxicology,
P G Baraldi, and B Cacciari, and A Guiotto, and R Romagnoli, and A N Zaid, and G Spalluto
Mismatch repair deficiency is associated with resistance to DNA minor groove alkylating agents.
May 1999, British journal of cancer,
P G Baraldi, and B Cacciari, and A Guiotto, and R Romagnoli, and A N Zaid, and G Spalluto
DNA-directed alkylating agents. 4. 4-anilinoquinoline-based minor groove directed aniline mustards.
May 1991, Journal of medicinal chemistry,
P G Baraldi, and B Cacciari, and A Guiotto, and R Romagnoli, and A N Zaid, and G Spalluto
From old alkylating agents to new minor groove binders.
January 2014, Critical reviews in oncology/hematology,
P G Baraldi, and B Cacciari, and A Guiotto, and R Romagnoli, and A N Zaid, and G Spalluto
Design, synthesis, and biological evaluation of DNA sequence and minor groove selective alkylating agents.
June 1993, Anti-cancer drug design,
P G Baraldi, and B Cacciari, and A Guiotto, and R Romagnoli, and A N Zaid, and G Spalluto
Hematopoietic toxicity and cell cycle perturbations induced by new DNA minor groove-alkylating agents.
September 1997, International journal of cancer,
P G Baraldi, and B Cacciari, and A Guiotto, and R Romagnoli, and A N Zaid, and G Spalluto
Out-of-shape DNA minor groove binders: induced fit interactions of heterocyclic dications with the DNA minor groove.
November 2005, Biochemistry,
P G Baraldi, and B Cacciari, and A Guiotto, and R Romagnoli, and A N Zaid, and G Spalluto
Chemistry of DNA minor groove binding agents.
October 2012, Journal of photochemistry and photobiology. B, Biology,
Copied contents to your clipboard!