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Article ; Online: Plain

Achanta, Prabhakar S / Chen, Shao-Nong / Pauli, Guido F

2021 Volume 59, Issue 7, Page(s) 746–751

Abstract: Favipiravir is an established antiviral that is currently being assessed as an investigational drug for the treatment of COVID-19. Favipiravir is strikingly similar to two molecules that the World Health Organization (WHO) lists as essential medicines, ... ...

Abstract	Favipiravir is an established antiviral that is currently being assessed as an investigational drug for the treatment of COVID-19. Favipiravir is strikingly similar to two molecules that the World Health Organization (WHO) lists as essential medicines, which also consist of a six-membered aromatic N-heterocycle bearing a carboxamide function: the anti-tuberculosis agent, pyrazinamide, and nicotinamide, also known as vitamin B
MeSH term(s)	Amides/analysis ; Amides/chemistry ; Antiviral Agents/analysis ; Antiviral Agents/chemistry ; Drug Contamination/prevention & control ; Niacinamide/analysis ; Niacinamide/chemistry ; Proton Magnetic Resonance Spectroscopy ; Pyrazinamide/analysis ; Pyrazinamide/chemistry ; Pyrazines/analysis ; Pyrazines/chemistry ; Quality Control ; World Health Organization
Chemical Substances	Amides ; Antiviral Agents ; Pyrazines ; Niacinamide (25X51I8RD4) ; Pyrazinamide (2KNI5N06TI) ; favipiravir (EW5GL2X7E0)
Language	English
Publishing date	2021-04-13
Publishing country	England
Document type	Letter
ZDB-ID	1475029-6
ISSN	1097-458X ; 0749-1581
ISSN (online)	1097-458X
ISSN	0749-1581
DOI	10.1002/mrc.5154
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Article ; Online: Development of Centrifugal Partition Chromatography for the Purification of Antibody–Drug Conjugates

Achanta, Prabhakar S. / Friesen, J. Brent / Harris, Guy / Webster, Gregory K. / Chen, Shao-Nong / Pauli, Guido F.

Analytical Chemistry. 2023 Jan. 26, v. 95, no. 5 p.2783-2788

2023

Abstract: Monoclonal antibody–drug conjugates (ADCs) are an expanding therapeutic class of biomolecules for which relatively few analytical and preparative separation options exist. Purification of ADCs with a specific drug antibody ratio is even more challenging. ...

Abstract	Monoclonal antibody–drug conjugates (ADCs) are an expanding therapeutic class of biomolecules for which relatively few analytical and preparative separation options exist. Purification of ADCs with a specific drug antibody ratio is even more challenging. We report the first application of countercurrent separation (CCS) to this problem. An ADC mimic was successfully chromatographed using an aqueous two-phase system (ATPS) consisting of PEG 1000/sodium citrate pH 7.5/water, 17.75/17.75/64.50 (w/w/w). Notably, different partition coefficients (K) in this ATPS for the ADC mimic (0.09 < K < 0.16) and its monoclonal antibody backbone, IgG (0.16 < K < 0.27), were observed using CCS. Differential elution behavior of such high-molecular-weight biomolecules, 146,441 vs. ∼150,000 Da, using CCS has no precedent. The results provide a proof of concept for further exploration of the application of ATPSs and CCS to the separation of ADCs.
Keywords	analytical chemistry ; biochemical compounds ; citrates ; countercurrent chromatography ; drugs ; monoclonal antibodies ; pH ; therapeutics
Language	English
Dates of publication	2023-0126
Size	p. 2783-2788.
Publishing place	American Chemical Society
Document type	Article ; Online
ZDB-ID	1508-8
ISSN	1520-6882 ; 0003-2700
ISSN (online)	1520-6882
ISSN	0003-2700
DOI	10.1021/acs.analchem.2c03919
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Article ; Online: Development of Centrifugal Partition Chromatography for the Purification of Antibody-Drug Conjugates.

Achanta, Prabhakar S / Friesen, J Brent / Harris, Guy / Webster, Gregory K / Chen, Shao-Nong / Pauli, Guido F

Analytical chemistry

2023 Volume 95, Issue 5, Page(s) 2783–2788

Abstract: Monoclonal antibody-drug conjugates (ADCs) are an expanding therapeutic class of biomolecules for which relatively few analytical and preparative separation options exist. Purification of ADCs with a specific drug antibody ratio is even more challenging. ...

Abstract	Monoclonal antibody-drug conjugates (ADCs) are an expanding therapeutic class of biomolecules for which relatively few analytical and preparative separation options exist. Purification of ADCs with a specific drug antibody ratio is even more challenging. We report the first application of countercurrent separation (CCS) to this problem. An ADC mimic was successfully chromatographed using an aqueous two-phase system (ATPS) consisting of PEG 1000/sodium citrate pH 7.5/water, 17.75/17.75/64.50 (w/w/w). Notably, different partition coefficients (
MeSH term(s)	Immunoconjugates ; Chromatography, Liquid ; Polyethylene Glycols/chemistry ; Water/chemistry ; Antibodies, Monoclonal
Chemical Substances	Immunoconjugates ; Polyethylene Glycols (3WJQ0SDW1A) ; Water (059QF0KO0R) ; Antibodies, Monoclonal
Language	English
Publishing date	2023-01-26
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	1508-8
ISSN	1520-6882 ; 0003-2700
ISSN (online)	1520-6882
ISSN	0003-2700
DOI	10.1021/acs.analchem.2c03919
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Article ; Online: Pharmaceutical analysis by NMR can accommodate strict impurity thresholds: The case of choline.

Achanta, Prabhakar S / Niemitz, Matthias / Friesen, J Brent / Tadjimukhamedov, Fatkhulla K / Bzhelyansky, Anton / Giancaspro, Gabriel I / Chen, Shao-Nong / Pauli, Guido F

Journal of pharmaceutical and biomedical analysis

2022 Volume 214, Page(s) 114709

Abstract: The ICH guidelines recommend reporting thresholds for regular impurities in drug substances at the level of 0.05% or 0.03% (w/w) depending on the maximum daily intake. Therefore, any instrumental method of analysis applicable to the impurity analysis ... ...

Abstract	The ICH guidelines recommend reporting thresholds for regular impurities in drug substances at the level of 0.05% or 0.03% (w/w) depending on the maximum daily intake. Therefore, any instrumental method of analysis applicable to the impurity analysis should be able to detect and quantify the analytes at those levels. This investigation was designed to verify the suitability of
MeSH term(s)	Choline ; Chromatography, High Pressure Liquid/methods ; Drug Contamination ; Magnetic Resonance Imaging/methods ; Magnetic Resonance Spectroscopy/methods ; Pharmaceutical Preparations
Chemical Substances	Pharmaceutical Preparations ; Choline (N91BDP6H0X)
Language	English
Publishing date	2022-03-05
Publishing country	England
Document type	Journal Article
ZDB-ID	604917-5
ISSN	1873-264X ; 0731-7085
ISSN (online)	1873-264X
ISSN	0731-7085
DOI	10.1016/j.jpba.2022.114709
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Article ; Online: Synthesis and antimicrobial evaluation of piperic acid amides and their lower homologues.

Achanta, Prabhakar S / Raj, Sneha / Horam, Soyar / Arockiaraj, Jesu / Bobbala, Ravi Kumar / Akkinepally, Raghuram Rao / Pasupuleti, Mukesh / Achanta, Appa Rao V N

Drug development research

2019 Volume 81, Issue 3, Page(s) 366–373

Abstract: ... on P. aeruginosa than on S. aureus. However, they did not exhibit potent activity on Vancomycin ... MDCA-AA, 2a) was found to be most active against S. aureus with MIC of 3.125 μg/ml. The PAS and INH ...

Abstract	Seven piperic acid amides along with their lower homologs (12) were synthesized using HATU-DIPEA coupling reagent. All the synthesized derivatives were evaluated for their antibacterial activities against Staphylococcus aureus, Pseudomonas aeruginosa, and vancomycin-resistant P. aeruginosa. They were found to be more active on P. aeruginosa than on S. aureus. However, they did not exhibit potent activity on Vancomycin resistant P. aeruginosa. Among the tested compounds, methylenedioxycinnamic acid amide of anthranilic acid (MDCA-AA, 2a) was found to be most active against S. aureus with MIC of 3.125 μg/ml. The PAS and INH amides of piperic acid were screened against Mycobacterium tuberculosis H37R
MeSH term(s)	Amides/chemical synthesis ; Amides/chemistry ; Amides/pharmacology ; Anti-Bacterial Agents/chemical synthesis ; Anti-Bacterial Agents/chemistry ; Anti-Bacterial Agents/pharmacology ; Fatty Acids, Unsaturated/chemical synthesis ; Fatty Acids, Unsaturated/chemistry ; Fatty Acids, Unsaturated/pharmacology ; Isoniazid/pharmacology ; Microbial Sensitivity Tests ; Mycobacterium tuberculosis/drug effects ; Pseudomonas aeruginosa/drug effects ; Staphylococcus aureus/drug effects ; Structure-Activity Relationship
Chemical Substances	Amides ; Anti-Bacterial Agents ; Fatty Acids, Unsaturated ; piperic acid (GFG3FLA9UR) ; Isoniazid (V83O1VOZ8L)
Language	English
Publishing date	2019-12-04
Publishing country	United States
Document type	Comparative Study ; Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	604587-x
ISSN	1098-2299 ; 0272-4391
ISSN (online)	1098-2299
ISSN	0272-4391
DOI	10.1002/ddr.21630
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Article ; Online: Stereochemistry of 2,2,5-trisubstituted tetrahydrofuran ring-containing natural products based on (1)H NMR spectroscopy: some observations.

Achanta, Prabhakar S / Akkinepally, Raghuram Rao / Bobbala, Ravi Kumar / Achanta, Appa Rao V N

Magnetic resonance in chemistry : MRC

2016 Volume 54, Issue 2, Page(s) 158–163

MeSH term(s)	Biological Products/chemistry ; Furans/chemistry ; Proton Magnetic Resonance Spectroscopy ; Stereoisomerism ; Triterpenes/chemistry
Chemical Substances	Biological Products ; Furans ; Triterpenes
Language	English
Publishing date	2016-02
Publishing country	England
Document type	Letter ; Research Support, Non-U.S. Gov't
ZDB-ID	1475029-6
ISSN	1097-458X ; 0749-1581
ISSN (online)	1097-458X
ISSN	0749-1581
DOI	10.1002/mrc.4329
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Article ; Online: Quantum mechanical NMR full spin analysis in pharmaceutical identity testing and quality control.

Achanta, Prabhakar S / Jaki, Birgit U / McAlpine, James B / Friesen, J Brent / Niemitz, Matthias / Chen, Shao-Nong / Pauli, Guido F

Journal of pharmaceutical and biomedical analysis

2020 Volume 192, Page(s) 113601

Abstract: Issues related to pharmaceutical quality are arising at an alarming rate. Pharmaceutical quality concerns both the Active Pharmaceutical Ingredients (APIs) and the Finished Drug Product/ Formulation. Recently, there has been a significant increase in the ...

Abstract	Issues related to pharmaceutical quality are arising at an alarming rate. Pharmaceutical quality concerns both the Active Pharmaceutical Ingredients (APIs) and the Finished Drug Product/ Formulation. Recently, there has been a significant increase in the number of reports of harmful impurities in marketed drug formulations. Impurities range from solvents, reactants, adulterants, and catalysts to synthetic byproducts. Quality concerns in commercial preparations may also arise due to shelf life stability. Furthermore, a number of falsified and substandard drug cases have been reported. Most of the techniques which are currently in place can, at best, detect the impurities, but cannot identify them unless they are already known and can be compared to a standard. On the other hand,
MeSH term(s)	Hydrogen ; Magnetic Resonance Imaging ; Magnetic Resonance Spectroscopy ; Pharmaceutical Preparations ; Quality Control
Chemical Substances	Pharmaceutical Preparations ; Hydrogen (7YNJ3PO35Z)
Language	English
Publishing date	2020-09-08
Publishing country	England
Document type	Journal Article ; Review
ZDB-ID	604917-5
ISSN	1873-264X ; 0731-7085
ISSN (online)	1873-264X
ISSN	0731-7085
DOI	10.1016/j.jpba.2020.113601
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Article ; Online: Rufomycins or Ilamycins: Naming Clarifications and Definitive Structural Assignments.

Zhou, Bin / Achanta, Prabhakar S / Shetye, Gauri / Chen, Shao-Nong / Lee, Hyun / Jin, Ying-Yu / Cheng, Jinhua / Lee, Mi-Jin / Suh, Joo-Won / Cho, Sanghyun / Franzblau, Scott G / Pauli, Guido F / McAlpine, James B

Journal of natural products

2021 Volume 84, Issue 10, Page(s) 2644–2663

Abstract: Rufomycin and ilamycin are synonymous for the same class of cyclopeptides, currently encompassing 33 structurally characterized isolates and 9 semisynthetic derivatives. Elucidation of new structures prioritized the consolidation of the names and ... ...

Abstract	Rufomycin and ilamycin are synonymous for the same class of cyclopeptides, currently encompassing 33 structurally characterized isolates and 9 semisynthetic derivatives. Elucidation of new structures prioritized the consolidation of the names and established the structures of four diastereoisomeric rufomycins with a 2-piperidinone, named rufomycins 4-7, including full
MeSH term(s)	Antitubercular Agents/chemistry ; Magnetic Resonance Spectroscopy ; Microbial Sensitivity Tests ; Molecular Structure ; Mycobacterium tuberculosis/drug effects ; Oligopeptides/chemistry ; Peptides, Cyclic/chemistry ; Terminology as Topic
Chemical Substances	Antitubercular Agents ; Oligopeptides ; Peptides, Cyclic ; rufomycin
Language	English
Publishing date	2021-10-10
Publishing country	United States
Document type	Journal Article
ZDB-ID	304325-3
ISSN	1520-6025 ; 0163-3864
ISSN (online)	1520-6025
ISSN	0163-3864
DOI	10.1021/acs.jnatprod.1c00198
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Article ; Online: New malabaricane triterpenes from the oleoresin of Ailanthus malabarica.

Achanta, Prabhakar S / Gattu, Rajesh Kumar / Belvotagi, Adavi Rao V / Akkinepally, Raghuram Rao / Bobbala, Ravi Kumar / Achanta, Appa Rao V N

Fitoterapia

2015 Volume 100, Page(s) 166–173

Abstract: Ten malabaricane type triterpenes were isolated from the oleoresin of Ailanthus malabarica, out of which six (1-6) were new. For three of the known compounds (7-9), NMR assignments are being reported for the first time. Compound 10, a known one, is a new ...

Abstract	Ten malabaricane type triterpenes were isolated from the oleoresin of Ailanthus malabarica, out of which six (1-6) were new. For three of the known compounds (7-9), NMR assignments are being reported for the first time. Compound 10, a known one, is a new report from this source. The structures were established by extensive 1D and 2D NMR spectroscopy. The oleoresin and some of the isolates did not possess antimicrobial activity and did not lyse RBCs.
MeSH term(s)	Ailanthus/chemistry ; Molecular Structure ; Plant Extracts/chemistry ; Triterpenes/chemistry ; Triterpenes/isolation & purification
Chemical Substances	Plant Extracts ; Triterpenes ; malabaricane ; oleoresins
Language	English
Publishing date	2015-01
Publishing country	Netherlands
Document type	Journal Article ; Research Support, Non-U.S. Gov't ; Research Support, U.S. Gov't, Non-P.H.S.
ZDB-ID	412385-2
ISSN	1873-6971 ; 0367-326X
ISSN (online)	1873-6971
ISSN	0367-326X
DOI	10.1016/j.fitote.2014.11.022
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Article: Rufomycins or Ilamycins: Naming Clarifications and Definitive Structural Assignments

Zhou, Bin / Achanta, Prabhakar S. / Shetye, Gauri / Chen, Shao-Nong / Lee, Hyun / Jin, Ying-Yu / Cheng, Jinhua / Lee, Mi-Jin / Suh, Joo-Won / Cho, Sanghyun / Franzblau, Scott G. / Pauli, Guido F. / McAlpine, James B.

Journal of natural products. 2021 Oct. 10, v. 84, no. 10

2021

Abstract	Rufomycin and ilamycin are synonymous for the same class of cyclopeptides, currently encompassing 33 structurally characterized isolates and 9 semisynthetic derivatives. Elucidation of new structures prioritized the consolidation of the names and established the structures of four diastereoisomeric rufomycins with a 2-piperidinone, named rufomycins 4–7, including full ¹H/¹³C NMR assignments. The characteristic HSQC cross-peak for the CH-5, the hemiaminal carbon in amino acid #5, allows assignment of the stereocenters C-4 and C-5 within this ring. Semisynthetic derivatives (rufomycinSS 1, 2, and 3) were prepared from a rufomycins 4 and 6 mixture to validate the structural assignments. Based on the X-ray crystal structures of rufomycins 2 and 4, considering the NMR differences of rufomycins 7 vs 4–6 compared to rufomycinSS 1 vs 2 and 3, and taking into account that two major conformers, A and B, occur in both rufomycinSS 2 and 3, structural modeling was pursued. Collectively, this paper discusses the NMR spectroscopic differences of the stereoisomers and their possible 3D conformers and correlates these with the anti-Mycobacterium tuberculosis activity. In addition, a look at the history prioritizes names and numbering schemes for this group of antibiotics and leads to consolidated nomenclature for all currently known members, natural and semisynthetic derivatives, and serves to accommodate future discoveries.
Keywords	X-radiation ; amino acids ; carbon ; stereoisomers ; tuberculosis
Language	English
Dates of publication	2021-1010
Size	p. 2644-2663.
Publishing place	American Chemical Society and American Society of Pharmacognosy
Document type	Article
ZDB-ID	304325-3
ISSN	1520-6025 ; 0163-3864
ISSN (online)	1520-6025
ISSN	0163-3864
DOI	10.1021/acs.jnatprod.1c00198
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