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Start Over Author "Mesini A" Journal journal of the american chemical society
10 results on '"Mesini A"'

1. Reversed and sandwiched analogs of duocarmycin SA: establishment of the origin of the sequence-selective alkylation of DNA and new insights into the source of catalysis

Author

Boger, Dale L., Bollinger, Bernd, Hertzog, Donald L., Johnson, Douglas S., Cai, Hui, Mesini, Philippe, Garbaccio, Robert M., Jin, Qing, and Kitos, Paul A.

Subjects
Alkylation -- Analysis, Cyclic compounds -- Analysis, Chemistry
Abstract

The origin of the DNA alkylation selectivity was evaluated through analysis of the reversed and sandwiched analogs of duocarmycin SA. Studies suggested that the ground state destabilization of the substrate disrupted the amide stabilization of the alkylation subunit and increased its reactivity toward nucleophiles. The DNA adenine-thymine minor grove binding mediates the reaction.

Published
1997

2. DNA alkylation properties of CC-1065 and duocarmycin analogs incorporating the 2,3,10,10a-tetrahydrocyclopropa(d)benzo(f)quinol-5-one alkylation subunit: identification of subtle structural features that contribute to the regioselectivity of the adenine N3 alkylation reaction

Author

Boger, Dale L. and Mesini, Philippe

Subjects
Alkylation -- Analysis, Organic compounds -- Research, Chemistry
Abstract

The adenine N3 alkylation is mediated by additional characteristics that resemble the imposed stereoelectronic control. Reactive 2,3,10,10a-tetrahydrocyclopropa(d)benzo(f)quinol-5-one (CBQ)-based agents alkylate same sites as the corresponding DSA-, CPI-, DA-, and CI-based agents. These agents have less selectivity among the established alkylation sites and low efficiency to alkylate DNA. Adducts obtained from adenine N3 addition to the least substituted cyclopropane carbon were detected under the relevant conditions of limiting agent.

Published
1995

3. Design, synthesis, and evaluation of CC-1065 and duocarmycin analogs incorporating the 2,3,10,10a-tetrahydro-1H-cyclopropa(d)benzo(f)quinol-5-one (CBQ) alkylation subunit: identification and structural origin of subtle stereoelectronic features that govern reactivity and regioselectivity

Author

Boger, Dale L. and Mesini, Philippe

Subjects
Antineoplastic antibiotics -- Research, Organic compounds -- Synthesis, Stereochemistry -- Analysis, Chemistry
Abstract

A new synthesis method is proposed for CC-1065 and duocarmycin analogs that incorporate the 2,3,10, 10a-tetrahydro-1H-cyclopropa(d)benzo(f)quinol-5-one (CBQ) alkylation subunit. The synthesis involves a key 6-exo-trig aryl radical alkene cyclization and subsequent Winstein Ar-3' alkylation. These CBQ-based analogs show marked solvolysis reactivity and mixed solvolysis regioselectivity. These analogs are highly stable and their potent activity is correlated with their chemical stability.

Published
1994

4. Reversed and Sandwiched Analogs of Duocarmycin SA: Establishment of the Origin of the Sequence-Selective Alkylation of DNA and New Insights into the Source of Catalysis

Author

Bernd Bollinger, Dale L. Boger, Qing Jin, Donald L. Hertzog, Paul A. Kitos, Hui Cai, Douglas S. Johnson, Robert M. Garbaccio, and Philippe Mesini

Subjects
Chemistry, Stereochemistry, Substituent, General Chemistry, Alkylation, Biochemistry, Catalysis, DNA Alkylation, chemistry.chemical_compound, Colloid and Surface Chemistry, Polynucleotide, Amide, Enantiomer, Selectivity, DNA
Abstract

The synthesis and examination of two unique classes of duocarmycin SA analogs are described which we refer to as reversed and sandwiched analogs. Their examination established both the origin of the DNA alkylation selectivity and that both enantiomers of this class of natural products are subject to the same polynucleotide recognition features. The most beautiful demonstration of this is the complete switch in the enantiomeric alkylation selectivity of the reversed analogs which is only consistent with the noncovalent binding model and incompatible with alkylation site models of the origin of the DNA alkylation selectivity. In addition, dramatic alterations in the rates of DNA alkylation were observed among the agents and correlate with the presence or absence of an extended, rigid N2 amide substituent. This has led to the proposal of a previously unrecognized source of catalysis for the DNA alkylation reaction which was introduced in the preceding paper of this issue (J. Am. Chem. Soc. 1997, 119, 4977−4986).

Published
1997

5. DNA Alkylation Properties of CC-1065 and Duocarmycin Analogs Incorporating the 2,3,10,10a-Tetrahydrocyclopropa[d]benzo[f]quinol-5-one Alkylation Subunit: Identification of Subtle Structural Features That Contribute to the Regioselectivity of the Adenine N3 Alkylation Reaction

Author

Philippe Mesini and Dale L. Boger

Subjects
chemistry.chemical_compound, DNA Alkylation, Colloid and Surface Chemistry, chemistry, Stereochemistry, Protein subunit, Regioselectivity, General Chemistry, Alkylation, Biochemistry, Catalysis, Duocarmycin
Published
1995

6. Design, Synthesis, and Evaluation of CC-1065 and Duocarmycin Analogs Incorporating the 2,3,10,10a-Tetrahydro-1H-cyclopropa[d]benzo[f]quinol-5-one (CBQ) Alkylation Subunit: Identification and Structural Origin of Subtle Stereoelectronic Features That Govern Reactivity and Regioselectivity

Author

Dale L. Boger and Philippe Mesini

Subjects
Stereochemistry, Chemistry, Protein subunit, Regioselectivity, General Chemistry, Alkylation, Biochemistry, Catalysis, chemistry.chemical_compound, Colloid and Surface Chemistry, Design synthesis, Reactivity (chemistry), Identification (biology), Duocarmycin
Published
1994

7. Formation of helical mesopores in organic polymer matrices

Author

Simon, Francois-Xavier, Khelfallah, Nawel S., Schmutz, Marc, Dfaz, Nancy, and Mesini, Philippe J.

Subjects
Polymers -- Structure, Polymers -- Chemical properties, Benzoic acid -- Chemical properties, Ethylene glycol -- Chemical properties, Transmission electron microscopes -- Usage, Chemistry
Abstract

Self-assembled helices are used as templates to form helical pores in organic matrices. The imprints are obtained with a high resolution and facilitated by the choice of a high cross-linking density network, which prevents any shrinking of the matrix.

Published
2007

8. Chemical and structural comparison of N-BOC-CBQ and N-BOC-CBI: identification and structural origin of an unappreciated but productive stability of the CC-1605 and duocarmycin SA alkylation subunits

Author

Boger, Dale L., Mesini, Philippe, and Tarby, Christine M.

Subjects
Antineoplastic agents -- Analysis, Electronic structure -- Analysis, Stereochemistry -- Analysis, Chemistry
Abstract

A five-membered ring, associated with the alkylation subunits of CC-1065 and duocarmycin, exhibits geometrical constraints that induce stereoelectronic control on the cleavage of cyclopropane that needs addition to the carbon with least substitution. Chemical and structural properties of N-BOC-CBQ and N-BOC-CB1 reveal the direct relationship of chemical stability to cytotoxic potency.

Published
1994

10. DNA alkylation properties of CC-1065 and duocarmycin analogs incorporating the 2,3,10,10-a...

Author

Boger, Dale L. and Mesini, Philippe

Subjects
*ADENINE nucleotides, *ALKYLATION
Abstract

Identifies subtle structural features that contribute to the regioselectivity of the adenine N3 alkylation reaction. Details of some DNA alkylation properties; Analyses on the adenine N3 adduct obtained by thermal depurination; Benefit of the regiochemcial course of the adenine N3 DNA alkylation reaction; Features that complement regioselectivity.

Published
1995
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