Quantum mechanics is especially useful in drug design when the mode of action of the drug involves a chemical reaction. Some advantages as well as caveats about the role of quantum mechanics in molecular modeling are reviewed.
BoydDBLipkowitzKB: Molecular mechanics: The method and its underlying philosophy. J Chem Educ1982;59: 269–274.
2.
LipkowitzKBBoydDB: Abstracts of Molecular Mechanics Symposium, Indiana University-Purdue University at Indianapolis, Indianapolis, IN. June 23–24, 1983.
3.
BurkertUAllingerNL: Molecular Mechanics, ACS Monograph 177. American Chemical Society, Washington, DC, 1982, and references cited therein.
4.
PullmanBPullmanA: Quantum Biochemistry. New York, Wiley-Interscience, 1963.
5.
BergmannEDPullmanB: Molecular and Quantum Pharmacology, Dordrecht, Holland; D. Reidel; 1974.
BoydDB: Notes on CNDO, INDO, MINDO, and MNDO. Quantum Chemistry Program Exchange Workshop on Practical Aspects of Quantum Chemistry, Indiana University, Bloomington, IN, June 21–26, 1981, and references cited therein.
8.
GormanDB: Theoretical and physicochemical studies on β-lactam antibiotics, MorinRBBoydM (eds): Chemistry and Biology of β-Lactam Antibiotics. New York, Academic Press, 1982vol 1, chap 5, pp 437–545, and references cited therein.
9.
DomelsmithLNEatonTAHoukKNPhotoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J Med Chem1981;24: 1414–1421.
10.
BoydDBMarshMM: Computational chemistry in the design of biologically active molecules at Lilly. Abstracts of 183rd American Chemical Society National Meeting, Las Vegas, Nevada, March 28-April 2, 1982, COMP 9.
11.
BoydDB: Electron density and dipole moment analysis of valence-electron wave functions. J Am Chem Soc1972;94: 64–70. Boyd DB: Electronic structures of cephalosporins and penicillins. III. EH and CNDO/2D electron density maps of 7-amino-3-cephem. J Phys Chem 1974; 78: 2604–2611.
12.
HalgrenTAKleierDAHallJHJr.: Speed and accuracy in molecular orbital calculations: A comparison of CNDO/2, INDO, PRDDO, STO-3G, and other methods, including AAMOM, VRDDO, and ESE MO. J Am Chem Soc1978;100: 6595–6608.
13.
DewarMJSFordGP: An addendum to a recent paper by Halgren, Lipscomb, and their co-workers concerning the relative accuracies of several current MO methods. J Am Chem Soc1979;101: 5558–5561.
14.
HavlasZMalonP: Molecular geometries: Accuracy test of the PCILO method. Coll Czech Chem Commun1980;45: 321–329.
15.
ZielinskiTJBreenDLReinR: AMINDO/3 study of some hydrogen-bonded systems. J Am Chem Soc1978;100: 6266–6267.
16.
KlopmanGAndreozziPHopfingerAJ: Hydrogen bonding in the MINDO/3 approximation. J Am Chem Soc1978;100: 6267–6268.
17.
YadavJSBarnickelGBradaczekH: Quantum chemical studies on the conformational structure of bacterial peptidoglycan. III. CNDO and INDO calculations on the N-acetyl-glucosamine. J Theor Biol1982;95: 167–179.
18.
MohammadNSHopfingerAJ: Treatment of hydrogen bonding within CNDO/2 and MINDO/3: CNDO/2H and MINDO/3H. Int J Quantum Chem1982;22: 1189–1207.
19.
DewarMJSThielW: Ground states of molecules. 39. MNDO results for molecules containing hydrogen, carbon, nitrogen, and oxygen. J Am Chem Soc1977;99: 4907–4917.
20.
DodziukH: The inapplicability of the MINDO/3 method to the conformational analysis of conjugated systems. J Mol Structure1979;55: 107–111.
21.
KollmanPAAllenLC: The theory of the hydrogen bond. Chem Rev1972;72: 283–303.
22.
GregoryARPaddon-RowMN: On the ability of the CNDO/2 and INDO MO methods to cope with nonbonded interactions. J Am Chem Soc1976;98: 7521–7523.
23.
BoydDB: Mapping electron density in molecules. Nonbonded contacts between lone pairs on divalent sulfurs.J Phys Chem1978;82: 1407–1416.
24.
Quantum mechanics aids antibiotic design.Chemical and Engineering News, June 16, 1980, p 27.
25.
TipperDJStromingerJL: Mechanism of action of penicillins: A proposal based on their structural similarity to acyl-D-alanyl-D-alanine. Proc Natl Acad Sci VSA1965;54: 1133–1141.
26.
SprattBG: The mechanism of action of penicillin. Sci Prog, Oxford, 65, 101–128 (1978).
27.
WaxmanDJYocumRRStromingerJL: Penicillins and cephalosporins are active site-directed acylating agents: Evidence in support of the substrate analogue hypothesis. Phil Trans Roy Soc Ser B, London, 1980, 289: 257–271.
28.
BoydDB: Theoretical studies of β-lactam antibiotics. Ann N Y Acad Sci1981;367: 531–542.
29.
MoewsPCKnoxJRWaxmanDJStromingerJL: Secondary structure relations between β-lactamases and penicillin-sensitive D-alanine-carboxypeptidases. Int J Peptide Protein Res1981;17: 211–218.
30.
KellyJAMoewsPCKnoxJR: Penicillin target enzyme and the antibiotic binding site. Science1982;218: 479–481.
31.
BoydDBHermannRBPrestiDEMarshMM: Electronic structures of cephalosporins and penicillins. 4. Modeling acylation by the β-lactam ring. J Med Chem1975;18: 408–417.
32.
BoydDBHerronDKLunnWHWSpitzerWA: Parabolic relationships between antibacterial activity of cephalosporins and β-lactam reactivity predicted from molecular orbital calculations. J Am Chem Soc1980;102: 1812–1814.
33.
CohenNC: β-lactam antibiotics: Geometrical requirements for antibacterial activities. J Med Chem1983;26: 259–264.
34.
FrereJMKellyJAKleinD: Δ2 and Δ3 cephalosporins, penicillinate and 6-unsubstituted penems: Intrinsic reactivity and interaction with β-lactamases and D-alanyl-D-alanine cleaving serine peptidases. Biochem J1982;203: 223–234.
35.
BoydDB: Substituents effects in cephalosporins as assessed by molecular orbital calculations, nuclear magnetic resonance, and kinetics. J Med Chem1983;26: 1010–1013.
36.
NishikawaJToriK: NMR studies of penicillins and cephalosporins. III. 3-Methylene substituent effect on structure-reactivity relationship of cephalosporins studied by carbon-13 NMR spectroscopy. J Antibiot1981;34: 1641–1644.
37.
SchanckACoeneBDereppeJMVanMeersscheM: Substituent effect on chemical reactivity of cephalosporins by kinetic and carbon-13 NMR. Bull Soc Chim Belg1983;92: 81–82.
