rudy potenzone - Academia.edu (original) (raw)

Papers by rudy potenzone

Carbohydrate Research, 1976

The geometry of the glycosidic valence-bond angle for both the beta-D-(1linked to4) and beta-D-(1... more The geometry of the glycosidic valence-bond angle for both the beta-D-(1linked to4) and beta-D-(1linked to 3) linkages has been investigated by using CNDO and PCILO molecularorbital techniques on model compounds. In each case, the glycosidic valence-bond angle of minimum energy was about 111 degrees, corresponding to the value observed in ether analogs. A secondary energy-minimum was found near 116 degrees, which is the value experimentally observed for saccharides. It was concluded that long-range intra-and/or inter-molecular interactions are responsible for overall preference for the 116 degrees value of the valence-bond angle. The force constants predicted from the shapes of the 116 degrees bond-angle minima gave poor agreement with the experimental values found for ethers and employed in normal coordinate analyses of saccharides. The results did suggest that the beta-D-(1linked to3) bond angle should be 115.6 degrees, which is smaller than the corresponding beta-D-(1linked to4) bond angle. An intrinsic torsional potential-function and general steric map were also determined for the torsion-angle rotations of the beta-D-(1linked to3) linkage.

PubMed, 1982

A quantitative structure-activity relationship (QSAR) based upon molecular shape analysis has bee... more A quantitative structure-activity relationship (QSAR) based upon molecular shape analysis has been developed for a set of 18 1-(X-phenyl)-3,3-dialkyltriazenes for which mutagenic potency is reported. An "active" molecular shape is proposed which suggests, in turn, a self-consistent mechanism for the microsomal hydroxylation of the nitrogen methyl group. A second QSAR has been constructed for an alternate set of 24 1-(X-phenyl)-3,3-dialkyltriazenes for which antitumor potency is reported. The QSAR suggests that the "active shape for antitumor potency is the same as that hypothesized for Ames mutagenic potency. A QSAR for a therapeutic index (TI) has been constructed to allow optimization of the difference between antitumor and mutagenic potencies. Large TIs require substituents on position 3 of the phenyl ring which are hydrophilic. The antitumor QSAR has been applied to three known compounds to test its reliability. A compound is predicted that is expected to have high antitumor activity and low mutagenicity. An overview of the methodology of molecular shape analysis, and its limitations, is included as part of this report on the development of QSARs.

Polymer Journal, Feb 1, 1978

We present the results of our theoretical conformational analysis of hyaluronic acid (HA) and sod... more We present the results of our theoretical conformational analysis of hyaluronic acid (HA) and sodium hyaluronate. Empirical potential energy functions for steric, electrostatic, hydrogen bonding, torsional, and solvation energies were used to evaluate the conformational energy with the CAMSEQ Software System. A trisaccharide model of the HA polymer was employed. Three chemical states were studied: HA-, charged HA in the absence of a counter-ion, neutral pH, and very low ionic strength; HAH, uncharged, protonated HA, low pH; HA-• Na +, charged HA with sodium ion present, neutral pH, and high ionic strength. Two sets of conformational energy data were collected. The first was generated by a series of sequential and random scans followed by gradient-search minimizations at each of the local minima. This was intended to give a general picture of the energy surface of each form of HA. The second data set consisted of 10,000 randomly generated conformations for each form. This was sufficient to account for the minima found in the first data set. The second set of energies was employed to estimate the partition function and corresponding chain dimensions for comparison with available hydrodynamic data. In addition, we compare and contrast our structural findings with the published crystal structures ofHA. KEY WORDS Hyaluronic Acid I Conformational Analysis I Glycosaminoglycans I * Sloan Research Fellow, to whom reprint requests should be sent. Early viscosity studies on HA isolated from vitreous humor, umbilical cord, and synovial fluid by Blix and Snellman 4 showed a molecular weight of 200,000 to 500,000 and particle lengths of 4800A to 10,000A. Several other molecular

Science, Jan 22, 1982

A publicly accessible computer system for chemical information has been developed jointly by a nu... more A publicly accessible computer system for chemical information has been developed jointly by a number of agencies of the U.S. government. The system contains spectroscopic, crystallographic, toxicological, and regulatory data for more than 200,000 chemicals. The entire data base may be searched for a particular chemical structure or substructure, whose properties may then be retrieved. Alternatively, searching with numeric properties data is possible, permitting the identification of chemicals. Access is by local telephone call, and the system is used on a fee-for-service basis by organizations in over 20 countries. An important application of the system is to problems of chemical pollution.

Carbohydrate Research, Apr 1, 1975

... I. Charge distributions, torsional potentials, and steric maps. Rudolph Potenzone, Jr. and An... more ... I. Charge distributions, torsional potentials, and steric maps. Rudolph Potenzone, Jr. and Anton J. Hopfinger Corresponding Author Contact Information. ... 11. EDT Atkins, R. Gansen, DH Isaac, V. Nandanwar and JK Sheehan. Polymer Lett. 10 (1972), p. 863. Full Text via CrossRef. ...

Trends in Analytical Chemistry, Nov 1, 1981

Biopolymers, Feb 1, 1980

Molecular mechanics calculations have been used to determine the preferred physical association s... more Molecular mechanics calculations have been used to determine the preferred physical association sites of the known alkylating agent dimethyl aziridinium ion (Az+) and a CH prototype test probe with B‐form, tetrameric DNA sequences. Electrostatic interactions are most important in determining these preferential physical association sites. In turn, the intermolecular energy minima depend on the charge distribution assigned to the DNA sequence. However, for three reported DNA charge distributions, only two distinct sets of energy minima were obtained for the CH‐like ion interacting with (G‐C)4, (A‐T)4, and [(G‐C)·(A‐T)]2 deoxyribonucleic acids. These minima correspond to physical association geometries in which the CH‐like ion is near known alkylation sites. The results of the Az+ … [(G‐C)·(A‐T)]2 interaction are virtually identical to those found for the CH‐like ion. Aqueous solvation energetics have little effect on the physical association of Az+ with [(G‐C)·(A‐T)]2.

Chemischer Informationsdienst, Apr 12, 1983

ChemInform Abstract Bei der Bromierung des Rotameren-Gemisches von (S)-(I) in Eisessig entstehen ... more ChemInform Abstract Bei der Bromierung des Rotameren-Gemisches von (S)-(I) in Eisessig entstehen regioselektiv die isomeren Brom-Rotameren (II) und (III), von denen das thermodynamisch weniger stabile cis-Rotamere (III) leicht durch direkte Kristallisation isoliert werden kann. Die strukturelle Zuordnung erfolgt durch-Röntgen-Einkristallstrukturanalyse. Die Verseifung liefert die (S)-Bromverbindung (IV). (IR-, NMR-, Massen-, Röntgen-Daten).

Trends in Analytical Chemistry, Oct 1, 1983

Computer readable analytical chemical data comments on a critical need Do academics, journal edit... more Computer readable analytical chemical data comments on a critical need Do academics, journal editors and research funding agencies place too little emphasis on the compilation of high quality data collections? Stephen Heller and Rudolph Potenzone think so, and contrast this situation with that found in industry, where large databanks abound.

Acs Symposium Series, Nov 28, 1979

ACS Symposium Series, 1979

Molecular pharmacology, 1982

A quantitative structure-activity relationship (QSAR) based upon molecular shape analysis has bee... more A quantitative structure-activity relationship (QSAR) based upon molecular shape analysis has been developed for a set of 18 1-(X-phenyl)-3,3-dialkyltriazenes for which mutagenic potency is reported. An "active" molecular shape is proposed which suggests, in turn, a self-consistent mechanism for the microsomal hydroxylation of the nitrogen methyl group. A second QSAR has been constructed for an alternate set of 24 1-(X-phenyl)-3,3-dialkyltriazenes for which antitumor potency is reported. The QSAR suggests that the "active shape for antitumor potency is the same as that hypothesized for Ames mutagenic potency. A QSAR for a therapeutic index (TI) has been constructed to allow optimization of the difference between antitumor and mutagenic potencies. Large TIs require substituents on position 3 of the phenyl ring which are hydrophilic. The antitumor QSAR has been applied to three known compounds to test its reliability. A compound is predicted that is expected to have hig...

Science, 1982

A publicly accessible computer system for chemical information has been developed jointly by a nu... more A publicly accessible computer system for chemical information has been developed jointly by a number of agencies of the U.S. government. The system contains spectroscopic, crystallographic, toxicological, and regulatory data for more than 200,000 chemicals. The entire data base may be searched for a particular chemical structure or substructure, whose properties may then be retrieved. Alternatively, searching with numeric properties data is possible, permitting the identification of chemicals. Access is by local telephone call, and the system is used on a fee-for-service basis by organizations in over 20 countries. An important application of the system is to problems of chemical pollution.

Biopolymers, 1980

Molecular mechanics calculations have been used to determine the preferred physical association s... more Molecular mechanics calculations have been used to determine the preferred physical association sites of the known alkylating agent dimethyl aziridinium ion (Az+) and a CH prototype test probe with B‐form, tetrameric DNA sequences. Electrostatic interactions are most important in determining these preferential physical association sites. In turn, the intermolecular energy minima depend on the charge distribution assigned to the DNA sequence. However, for three reported DNA charge distributions, only two distinct sets of energy minima were obtained for the CH‐like ion interacting with (G‐C)4, (A‐T)4, and [(G‐C)·(A‐T)]2 deoxyribonucleic acids. These minima correspond to physical association geometries in which the CH‐like ion is near known alkylation sites. The results of the Az+ … [(G‐C)·(A‐T)]2 interaction are virtually identical to those found for the CH‐like ion. Aqueous solvation energetics have little effect on the physical association of Az+ with [(G‐C)·(A‐T)]2.

Biopolymers, 1980

Molecular mechanics calculations have been used to determine the preferred physical association s... more Molecular mechanics calculations have been used to determine the preferred physical association sites of the known alkylating agent dimethyl aziridinium ion (Az+) and a CH prototype test probe with B-form, tetrameric DNA sequences. Electrostatic interactions are most important in determining these preferential physical association sites. In turn, the intermolecular energy minima depend on the charge distribution assigned to the DNA sequence. However, for three reported DNA charge distributions, only two distinct sets of energy minima were obtained for the CH-like ion interacting with (G-C)4, (A-T)4, and [(G-C)·(A-T)]2 deoxyribonucleic acids. These minima correspond to physical association geometries in which the CH-like ion is near known alkylation sites. The results of the Az+ … [(G-C)·(A-T)]2 interaction are virtually identical to those found for the CH-like ion. Aqueous solvation energetics have little effect on the physical association of Az+ with [(G-C)·(A-T)]2.

Journal of Organic Chemistry, 1982

Science, 1982

A publicly accessible computer system for chemical information has been developed jointly by a nu... more A publicly accessible computer system for chemical information has been developed jointly by a number of agencies of the U.S. government. The system contains spectroscopic, crystallographic, toxicological, and regulatory data for more than 200,000 chemicals. The entire data base may be searched for a particular chemical structure or substructure, whose properties may then be retrieved. Alternatively, searching with numeric properties data is possible, permitting the identification of chemicals. Access is by local telephone call, and the system is used on a fee-for-service basis by organizations in over 20 countries. An important application of the system is to problems of chemical pollution.

Carbohydrate Research, 1976

The geometry of the glycosidic valence-bond angle for both the beta-D-(1linked to4) and beta-D-(1... more The geometry of the glycosidic valence-bond angle for both the beta-D-(1linked to4) and beta-D-(1linked to 3) linkages has been investigated by using CNDO and PCILO molecularorbital techniques on model compounds. In each case, the glycosidic valence-bond angle of minimum energy was about 111 degrees, corresponding to the value observed in ether analogs. A secondary energy-minimum was found near 116 degrees, which is the value experimentally observed for saccharides. It was concluded that long-range intra-and/or inter-molecular interactions are responsible for overall preference for the 116 degrees value of the valence-bond angle. The force constants predicted from the shapes of the 116 degrees bond-angle minima gave poor agreement with the experimental values found for ethers and employed in normal coordinate analyses of saccharides. The results did suggest that the beta-D-(1linked to3) bond angle should be 115.6 degrees, which is smaller than the corresponding beta-D-(1linked to4) bond angle. An intrinsic torsional potential-function and general steric map were also determined for the torsion-angle rotations of the beta-D-(1linked to3) linkage.

PubMed, 1982

A quantitative structure-activity relationship (QSAR) based upon molecular shape analysis has bee... more A quantitative structure-activity relationship (QSAR) based upon molecular shape analysis has been developed for a set of 18 1-(X-phenyl)-3,3-dialkyltriazenes for which mutagenic potency is reported. An "active" molecular shape is proposed which suggests, in turn, a self-consistent mechanism for the microsomal hydroxylation of the nitrogen methyl group. A second QSAR has been constructed for an alternate set of 24 1-(X-phenyl)-3,3-dialkyltriazenes for which antitumor potency is reported. The QSAR suggests that the "active shape for antitumor potency is the same as that hypothesized for Ames mutagenic potency. A QSAR for a therapeutic index (TI) has been constructed to allow optimization of the difference between antitumor and mutagenic potencies. Large TIs require substituents on position 3 of the phenyl ring which are hydrophilic. The antitumor QSAR has been applied to three known compounds to test its reliability. A compound is predicted that is expected to have high antitumor activity and low mutagenicity. An overview of the methodology of molecular shape analysis, and its limitations, is included as part of this report on the development of QSARs.

Polymer Journal, Feb 1, 1978

We present the results of our theoretical conformational analysis of hyaluronic acid (HA) and sod... more We present the results of our theoretical conformational analysis of hyaluronic acid (HA) and sodium hyaluronate. Empirical potential energy functions for steric, electrostatic, hydrogen bonding, torsional, and solvation energies were used to evaluate the conformational energy with the CAMSEQ Software System. A trisaccharide model of the HA polymer was employed. Three chemical states were studied: HA-, charged HA in the absence of a counter-ion, neutral pH, and very low ionic strength; HAH, uncharged, protonated HA, low pH; HA-• Na +, charged HA with sodium ion present, neutral pH, and high ionic strength. Two sets of conformational energy data were collected. The first was generated by a series of sequential and random scans followed by gradient-search minimizations at each of the local minima. This was intended to give a general picture of the energy surface of each form of HA. The second data set consisted of 10,000 randomly generated conformations for each form. This was sufficient to account for the minima found in the first data set. The second set of energies was employed to estimate the partition function and corresponding chain dimensions for comparison with available hydrodynamic data. In addition, we compare and contrast our structural findings with the published crystal structures ofHA. KEY WORDS Hyaluronic Acid I Conformational Analysis I Glycosaminoglycans I * Sloan Research Fellow, to whom reprint requests should be sent. Early viscosity studies on HA isolated from vitreous humor, umbilical cord, and synovial fluid by Blix and Snellman 4 showed a molecular weight of 200,000 to 500,000 and particle lengths of 4800A to 10,000A. Several other molecular

Science, Jan 22, 1982

A publicly accessible computer system for chemical information has been developed jointly by a nu... more A publicly accessible computer system for chemical information has been developed jointly by a number of agencies of the U.S. government. The system contains spectroscopic, crystallographic, toxicological, and regulatory data for more than 200,000 chemicals. The entire data base may be searched for a particular chemical structure or substructure, whose properties may then be retrieved. Alternatively, searching with numeric properties data is possible, permitting the identification of chemicals. Access is by local telephone call, and the system is used on a fee-for-service basis by organizations in over 20 countries. An important application of the system is to problems of chemical pollution.

Carbohydrate Research, Apr 1, 1975

... I. Charge distributions, torsional potentials, and steric maps. Rudolph Potenzone, Jr. and An... more ... I. Charge distributions, torsional potentials, and steric maps. Rudolph Potenzone, Jr. and Anton J. Hopfinger Corresponding Author Contact Information. ... 11. EDT Atkins, R. Gansen, DH Isaac, V. Nandanwar and JK Sheehan. Polymer Lett. 10 (1972), p. 863. Full Text via CrossRef. ...

Trends in Analytical Chemistry, Nov 1, 1981

Biopolymers, Feb 1, 1980

Molecular mechanics calculations have been used to determine the preferred physical association s... more Molecular mechanics calculations have been used to determine the preferred physical association sites of the known alkylating agent dimethyl aziridinium ion (Az+) and a CH prototype test probe with B‐form, tetrameric DNA sequences. Electrostatic interactions are most important in determining these preferential physical association sites. In turn, the intermolecular energy minima depend on the charge distribution assigned to the DNA sequence. However, for three reported DNA charge distributions, only two distinct sets of energy minima were obtained for the CH‐like ion interacting with (G‐C)4, (A‐T)4, and [(G‐C)·(A‐T)]2 deoxyribonucleic acids. These minima correspond to physical association geometries in which the CH‐like ion is near known alkylation sites. The results of the Az+ … [(G‐C)·(A‐T)]2 interaction are virtually identical to those found for the CH‐like ion. Aqueous solvation energetics have little effect on the physical association of Az+ with [(G‐C)·(A‐T)]2.

Chemischer Informationsdienst, Apr 12, 1983

ChemInform Abstract Bei der Bromierung des Rotameren-Gemisches von (S)-(I) in Eisessig entstehen ... more ChemInform Abstract Bei der Bromierung des Rotameren-Gemisches von (S)-(I) in Eisessig entstehen regioselektiv die isomeren Brom-Rotameren (II) und (III), von denen das thermodynamisch weniger stabile cis-Rotamere (III) leicht durch direkte Kristallisation isoliert werden kann. Die strukturelle Zuordnung erfolgt durch-Röntgen-Einkristallstrukturanalyse. Die Verseifung liefert die (S)-Bromverbindung (IV). (IR-, NMR-, Massen-, Röntgen-Daten).

Trends in Analytical Chemistry, Oct 1, 1983

Computer readable analytical chemical data comments on a critical need Do academics, journal edit... more Computer readable analytical chemical data comments on a critical need Do academics, journal editors and research funding agencies place too little emphasis on the compilation of high quality data collections? Stephen Heller and Rudolph Potenzone think so, and contrast this situation with that found in industry, where large databanks abound.

Acs Symposium Series, Nov 28, 1979

ACS Symposium Series, 1979

Molecular pharmacology, 1982

A quantitative structure-activity relationship (QSAR) based upon molecular shape analysis has bee... more A quantitative structure-activity relationship (QSAR) based upon molecular shape analysis has been developed for a set of 18 1-(X-phenyl)-3,3-dialkyltriazenes for which mutagenic potency is reported. An "active" molecular shape is proposed which suggests, in turn, a self-consistent mechanism for the microsomal hydroxylation of the nitrogen methyl group. A second QSAR has been constructed for an alternate set of 24 1-(X-phenyl)-3,3-dialkyltriazenes for which antitumor potency is reported. The QSAR suggests that the "active shape for antitumor potency is the same as that hypothesized for Ames mutagenic potency. A QSAR for a therapeutic index (TI) has been constructed to allow optimization of the difference between antitumor and mutagenic potencies. Large TIs require substituents on position 3 of the phenyl ring which are hydrophilic. The antitumor QSAR has been applied to three known compounds to test its reliability. A compound is predicted that is expected to have hig...

Science, 1982

A publicly accessible computer system for chemical information has been developed jointly by a nu... more A publicly accessible computer system for chemical information has been developed jointly by a number of agencies of the U.S. government. The system contains spectroscopic, crystallographic, toxicological, and regulatory data for more than 200,000 chemicals. The entire data base may be searched for a particular chemical structure or substructure, whose properties may then be retrieved. Alternatively, searching with numeric properties data is possible, permitting the identification of chemicals. Access is by local telephone call, and the system is used on a fee-for-service basis by organizations in over 20 countries. An important application of the system is to problems of chemical pollution.

Biopolymers, 1980

Molecular mechanics calculations have been used to determine the preferred physical association s... more Molecular mechanics calculations have been used to determine the preferred physical association sites of the known alkylating agent dimethyl aziridinium ion (Az+) and a CH prototype test probe with B‐form, tetrameric DNA sequences. Electrostatic interactions are most important in determining these preferential physical association sites. In turn, the intermolecular energy minima depend on the charge distribution assigned to the DNA sequence. However, for three reported DNA charge distributions, only two distinct sets of energy minima were obtained for the CH‐like ion interacting with (G‐C)4, (A‐T)4, and [(G‐C)·(A‐T)]2 deoxyribonucleic acids. These minima correspond to physical association geometries in which the CH‐like ion is near known alkylation sites. The results of the Az+ … [(G‐C)·(A‐T)]2 interaction are virtually identical to those found for the CH‐like ion. Aqueous solvation energetics have little effect on the physical association of Az+ with [(G‐C)·(A‐T)]2.

Biopolymers, 1980

Molecular mechanics calculations have been used to determine the preferred physical association s... more Molecular mechanics calculations have been used to determine the preferred physical association sites of the known alkylating agent dimethyl aziridinium ion (Az+) and a CH prototype test probe with B-form, tetrameric DNA sequences. Electrostatic interactions are most important in determining these preferential physical association sites. In turn, the intermolecular energy minima depend on the charge distribution assigned to the DNA sequence. However, for three reported DNA charge distributions, only two distinct sets of energy minima were obtained for the CH-like ion interacting with (G-C)4, (A-T)4, and [(G-C)·(A-T)]2 deoxyribonucleic acids. These minima correspond to physical association geometries in which the CH-like ion is near known alkylation sites. The results of the Az+ … [(G-C)·(A-T)]2 interaction are virtually identical to those found for the CH-like ion. Aqueous solvation energetics have little effect on the physical association of Az+ with [(G-C)·(A-T)]2.

Journal of Organic Chemistry, 1982

Science, 1982

A publicly accessible computer system for chemical information has been developed jointly by a nu... more A publicly accessible computer system for chemical information has been developed jointly by a number of agencies of the U.S. government. The system contains spectroscopic, crystallographic, toxicological, and regulatory data for more than 200,000 chemicals. The entire data base may be searched for a particular chemical structure or substructure, whose properties may then be retrieved. Alternatively, searching with numeric properties data is possible, permitting the identification of chemicals. Access is by local telephone call, and the system is used on a fee-for-service basis by organizations in over 20 countries. An important application of the system is to problems of chemical pollution.