Molecular Fingerprint Recombination: Generating Hybrid Fingerprints for Similarity Searching from Different Fingerprint Types

Nisius, Britta; Bajorath, Jürgen

doi:10.1002/cmdc.200900243

Cited by 38 publications

(36 citation statements)

References 30 publications

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“…However, alternative methods using other types of fingerprints or molecular descriptors could still be explored [44], [45]. Another possibility for further study is the construction of similar models taking into account the 3D most stable conformation in drugs [46].…”

Section: Discussionmentioning

confidence: 99%

Enhancing Adverse Drug Event Detection in Electronic Health Records Using Molecular Structure Similarity: Application to Pancreatitis

et al. 2012

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Background Adverse drug events (ADEs) detection and assessment is at the center of pharmacovigilance. Data mining of systems, such as FDA’s Adverse Event Reporting System (AERS) and more recently, Electronic Health Records (EHRs), can aid in the automatic detection and analysis of ADEs. Although different data mining approaches have been shown to be valuable, it is still crucial to improve the quality of the generated signals. Objective To leverage structural similarity by developing molecular fingerprint-based models (MFBMs) to strengthen ADE signals generated from EHR data. Methods A reference standard of drugs known to be causally associated with the adverse event pancreatitis was used to create a MFBM. Electronic Health Records (EHRs) from the New York Presbyterian Hospital were mined to generate structured data. Disproportionality Analysis (DPA) was applied to the data, and 278 possible signals related to the ADE pancreatitis were detected. Candidate drugs associated with these signals were then assessed using the MFBM to find the most promising candidates based on structural similarity. Results The use of MFBM as a means to strengthen or prioritize signals generated from the EHR significantly improved the detection accuracy of ADEs related to pancreatitis . MFBM also highlights the etiology of the ADE by identifying structurally similar drugs, which could follow a similar mechanism of action. Conclusion The method proposed in this paper provides evidence of being a promising adjunct to existing automated ADE detection and analysis approaches.

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Section: Discussionmentioning

confidence: 99%

Enhancing Adverse Drug Event Detection in Electronic Health Records Using Molecular Structure Similarity: Application to Pancreatitis

et al. 2012

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“…3b). These hybrid fingerprints illustrate the complementary nature of different chemical reference space representations and corresponding fingerprint designs [66].…”

Section: Molecular Fingerprints and Their Selection Methodsmentioning

confidence: 99%

Descriptors and their selection methods in QSAR analysis: paradigm for drug design

Danishuddin

Khan

2016

Drug Discovery Today

272

126

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“…These hybrids were generated by merging best-performing feature subsets from fingerprints of different design, for example, structural fragment and 2D pharmacophore fingerprints, as illustrated in Figure 2. These hybrid fingerprints often further improved the search performance of reduced fingerprints, which illustrates the complementary nature of different chemical reference space representations and corresponding fingerprint designs [72].…”

Section: Fingerprint Reduction Approachesmentioning

confidence: 99%

“…These findings were also consistent with observations made when applying the bit silencing technique, as described above. Moreover, fingerprint reduction was also followed by a fingerprint 'recombination' step to generate compound class-directed 'hybrid fingerprints' [72]. These hybrids were generated by merging best-performing feature subsets from fingerprints of different design, for example, structural fragment and 2D pharmacophore fingerprints, as illustrated in Figure 2.…”

Section: Fingerprint Reduction Approachesmentioning

confidence: 99%

Advances in 2D fingerprint similarity searching

Geppert¹,

Bajorath²

2010

Expert Opinion on Drug Discovery

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The reader is provided with an overview of the state-of-the-art fingerprint design and search strategies developed. It will be possible to rationalize opportunities and limitations of 2D fingerprint similarity searching. Take home messages: Fingerprint search calculations are more complex than it might appear at first glance and susceptible to complications that are often overlooked in practical applications. Fingerprint search performance typically only depends on relatively small subsets of bit positions. Recently, different fingerprint engineering strategies have been applied to 'tune' existing fingerprints in a compound class-directed manner. Fingerprints have substantial scaffold hopping potential, despite the simplicity of their design.

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Molecular Fingerprint Recombination: Generating Hybrid Fingerprints for Similarity Searching from Different Fingerprint Types

Cited by 38 publications

References 30 publications

Enhancing Adverse Drug Event Detection in Electronic Health Records Using Molecular Structure Similarity: Application to Pancreatitis

Enhancing Adverse Drug Event Detection in Electronic Health Records Using Molecular Structure Similarity: Application to Pancreatitis

Descriptors and their selection methods in QSAR analysis: paradigm for drug design

Advances in 2D fingerprint similarity searching

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